1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine [DOI] by Asch

Reaxys

PubChem

eMolecules

Reactions (15)

Substances (18)

Structure

Citations (326)

Structure/Compound Data Chemical Name: [125I]-DOI

N° of preparations All Preps | All Reactions

Available Data

N° of ref.

no reactions.

Bioactivity (2)

Reaxys Registry Number: 10439827

Type of Substance: isocyclic Molecular Formula: C11H16INO2

Linear Structure Formula: C11H16(125)INO2

Molecular Weight: 319.254

InChI Key: BGMZUEKZENQUJY-DACUFJSSSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms [125I]-DOI, [125I]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane, [125I](±)DOI Bioactivity Pharmacological Data (2) 1 of 2

2 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike

Naunyn-Schmiedeberg's Archives of Pharmacology, 2004 , vol. 370, # 2 p. 114 - 123 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

HEK-293 cell membranes expressing human 5-HT2A receptor

Concentration (Pharmacological Data)

0.1 - 20 nmol/l

Method (Pharmacological Data)

saturation binding assay; <3H>-labeled title comp. used as radioligand; membranes incubated with radioligand for 1 h at 37 deg C in assay buffer supplemented with 5 mmol/l CaCl2; radioactivity quantified by scintillation spectrophotometry

Further Details (Pharmacological Data)

assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.36 nmol/l

Reference

Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike

Naunyn-Schmiedeberg's Archives of Pharmacology, 2004 , vol. 370, # 2 p. 114 - 123 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 4-iodo-2,5-dimethoxyphenylisopropylamine Reaxys Registry Number: 2727017

CAS Registry Number: 64584-34-5, 82830-53-3, 82864-06-0, 99665-04-0 Type of Substance: isocyclic Molecular Formula: C11H16INO2

Linear Structure Formula: C11H16INO2

Molecular Weight: 321.158

InChI Key: BGMZUEKZENQUJY-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms 4-iodo-2,5-dimethoxyphenylisopropylamine, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane Identification Substance Label (12) Label

Reference

DOI

Le Grand; Talmant; Rieu; Patoiseau; Colpaert; John

Journal of Cardiovascular Pharmacology, 1995 , vol. 26, # 5 p. 803 - 809 Title/Abstract Full Text View citing articles Show Details

Sanchez

Pharmacology and Toxicology, 1995 , vol. 77, # 1 p. 71 - 78 Title/Abstract Full Text View citing articles Show Details

Yamada; Sugimoto; Horisaka

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 11 p. 1580 - 1583 Title/Abstract Full Text View citing articles Show Details

Garnovskaya; Nebigil; Arthur; Spurney; Raymond

Molecular Pharmacology, 1995 , vol. 48, # 2 p. 230 - 237 Title/Abstract Full Text View citing articles Show Details

Mundey; Fletcher; Marsden

British Journal of Pharmacology, 1996 , vol. 117, # 4 p. 750 - 756 Title/Abstract Full Text View citing articles Show Details

Padoin; Lucion

European Journal of Pharmacology, 1995 , vol. 277, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Nankai; Yamada; Muneoka; Toru

European Journal of Pharmacology, 1995 , vol. 281, # 2 p. 123 - 130 Title/Abstract Full Text View citing articles Show Details

Schreiber; Brocco; Audinot; Gobert; Veiga; Millan

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 273, # 1 p. 101 - 112 Title/Abstract Full Text View citing articles Show Details

Eison; Freeman; Cuss; Mullins; Wright

4 prep out of 5 reactions.

Identification Physical Data (2) Spectra (2) Bioactivity (176) Other Data (15)

242

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 273, # 1 p. 304 - 308 Title/Abstract Full Text View citing articles Show Details

Ullmer; Boddeke; Schmuck; Lubbert

British Journal of Pharmacology, 1996 , vol. 117, # 6 p. 1081 - 1088 Title/Abstract Full Text View citing articles Show Details

Chen; Li; Chuang

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 2 p. 674 - 680 Title/Abstract Full Text View citing articles Show Details

Sleight, Andrew J.; Stam, Nico J.; Mutel, Vincent; Vanderheyden, Patrick M. L.

Biochemical Pharmacology, 1996 , vol. 51, # 1 p. 71 - 76 Title/Abstract Full Text View citing articles Show Details

Hillegaart; Estival; Ahlenius

European Journal of Pharmacology, 1996 , vol. 295, # 2-3 p. 155 - 161 Title/Abstract Full Text View citing articles Show Details

Berendsen, Hemmie H.G.; Kester, Robert C.H.; Peeters, Bernard W.M.M.; Broekkamp, Chris L.E.

European Journal of Pharmacology, 1996 , vol. 308, # 2 p. 103 - 111 Title/Abstract Full Text View citing articles Show Details

Roth; Palvimaki; Berry; Khan; Sachs; Uluer; Choudhary

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 3 p. 1638 - 1646 Title/Abstract Full Text View citing articles Show Details

Pauwels, Petrus J.; Wurch, Thierry; Palmier, Christiane; Colpaert, Francis C.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 2 p. 136 - 144 Title/Abstract Full Text View citing articles Show Details

Krebs-Thomson, Kirsten; Lehmann-Masten, Virginia; Naiem, Shahrouz; Paulus, Martin P.; Geyer, Mark A.

European Journal of Pharmacology, 1998 , vol. 343, # 2-3 p. 135 - 143 Title/Abstract Full Text View citing articles Show Details

Cussac, Didier; Newman-Tancredi, Adrian; Quentric, Yann; Carpentier, Nathalie; Poissonnet, Guillaume; Parmentier, Jean-Gilles; Goldstein, Solo; Millan, Mark J.

Naunyn-Schmiedeberg's Archives of Pharmacology, 2002 , vol. 365, # 3 p. 242 - 252 Title/Abstract Full Text View citing articles Show Details

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

Tian, Run-Xian; Kimura, Shoji; Kondou, Naoki; Fujisawa, Yoshihide; Zhou, Ming-Sheng; Yoneyama, Hirohito; Kosaka, Hiroaki; Rahman, Matlubur; Nishiyama, Akira; Abe, Youichi

European journal of pharmacology, 2002 , vol. 437, # 1-2 p. 79 - 84 Title/Abstract Full Text View citing articles Show Details

Willins, David L.; Meltzer, Herbert Y.

Journal of Pharmacology and Experimental Therapeutics, 1997 , vol. 282, # 2 p. 699 - 706 Title/Abstract Full Text View citing articles Show Details

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Marek, Gerard J.; Aghajanian, George K.

Journal of Pharmacology and Experimental Therapeutics, 1996 , vol. 278, # 3 p. 1373 - 1382 Title/Abstract Full Text View citing articles Show Details

Locher, Christopher P.; Ruben, Peter C.; Gut, Jiri; Rosenthal, Philip J.

Antimicrobial Agents and Chemotherapy, 2003 , vol. 47, # 12 p. 3806 - 3809 Title/Abstract Full Text View citing articles Show Details

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Sugimoto; Yamada

Biological and pharmaceutical bulletin, 2000 , vol. 23, # 12 p. 1521 - 1523 Title/Abstract Full Text View citing articles Show Details

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero

Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details

INTRA-CELLULAR THERAPIES, INC.; VANOVER, Kimberly; LI, Peng; MATES, Sharon; DAVIS, Robert; WENNOGLE, Lawrence P.

Patent: WO2015/85004 A1, 2015 ; Title/Abstract Full Text Show Details

Mori, Tomohisa; Uzawa, Naoki; Iwase, Yoshiyuki; Masukawa, Daiki; Rahmadi, Mahardian; Hirayama, Shigeto; Hokazono, Mayuna; Higashiyama, Kimio; Shioda, Seiji; Suzuki, Tsutomu

Psychopharmacology, 2016 , vol. 233, # 12 p. 2343 - 2353 Title/Abstract Full Text View citing articles Show Details

Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4346 - 4351 Title/Abstract Full Text View citing articles Show Details

UNIVERSITÉ LAVAL; GUERTIN, Pierre

Patent: WO2015/127556 A1, 2015 ; Title/Abstract Full Text Show Details

5; DOI

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 8 p. 4661 - 4669 Title/Abstract Full Text View citing articles Show Details

rac-DOI

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309

Title/Abstract Full Text View citing articles Show Details

1c, DOI

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.

Medicinal Chemistry Research, 1995 , vol. 5, # 9 p. 651 - 663 Title/Abstract Full Text Show Details

DOI, Fig. 4

Zethof, Theo J. J.; Van der Heyden, Jan A. M.; Tolboom, Jeroen T. B. M.; Olivier, Berend

European Journal of Pharmacology, 1995 , vol. 294, # 1 p. 125 - 136 Title/Abstract Full Text View citing articles Show Details

(+/-)DOI

Odagaki; Fuxe

European Journal of Pharmacology - Molecular Pharmacology Section, 1995 , vol. 288, # 3 p. 385 - 388 Title/Abstract Full Text View citing articles Show Details

Dawson, Brian A.; Black, D. B.; Sy, W.-W.; Graham, K.

Magnetic Resonance in Chemistry, 1994 , vol. 32, # 9 p. 557 - 558 Title/Abstract Full Text Show Details

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon

Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

Braun et al.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 1543 Full Text View citing articles Show Details

Coutts; Malicky

Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (2) Related Markush Structure (RN)

Location in Patent

Reference Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.

Patent: US2007/27208 A1, 2007 ;

11337200

Title/Abstract Full Text Show Details

Claim

Luminis Pty Limited

Patent: US6403651 B1, 2002 ; Title/Abstract Full Text Show Details

Board of Supervisors of Louisiana State University; Agricultural and Mechanical College

Patent: US5417987 A1, 1995 ; Title/Abstract Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

Hydrochlorid: F.: 200.5-201.5grad

Braun et al.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 1543 Full Text View citing articles Show Details

Physical Data Chromatographic Data (2) Chromatographic data

Reference

GC (Gas chromatography)

Robayo, Diego A. Snchez; Mendez, William F. Garzn; Ocampo, Gonzalo Taborda; Moreano, Milton Rosero

Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 6 p. 992 - 997 Title/Abstract Full Text View citing articles Show Details

CE (Capillar electrophoresis)

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero

Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Temperature (NMR Spectroscopy)

Chemical shifts

13C

CDCl3

26.9 °C

Reference Dawson, Brian A.; Black, D. B.; Sy, W.-W.; Graham, K.

Magnetic Resonance in Chemistry, 1994 , vol. 32, # 9 p. 557 - 558 Title/Abstract Full Text Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

gas chromatography mass spectrometry (GCMS) IT (ion trap) spectrum

Robayo, Diego A. Snchez; Mendez, William F. Garzn; Ocampo, Gonzalo Taborda; Moreano, Milton Rosero

Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 6 p. 992 - 997 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (174) 1 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Coutts; Malicky

Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409 Title/Abstract Full Text View citing articles Show Details

American Home Products Corporation

Patent: US2001/51622 A1, 2001 ; Title/Abstract Full Text Show Details

Synaptic Pharmaceutical Corporation

Patent: US5476782 A1, 1995 ; Title/Abstract Full Text Show Details

Washington University

Patent: US5958919 A1, 1999 ; Title/Abstract Full Text Show Details

Olney, John W.; Farber, Nuri B.

Patent: US6391871 B1, 2002 ; Title/Abstract Full Text Show Details

Luminis Pty Limited

Patent: US6403651 B1, 2002 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US6476032 B2, 2002 ; Title/Abstract Full Text Show Details

May, Jesse A.; Zinke, Paul W.

Patent: US2003/83346 A1, 2003 ; Title/Abstract Full Text Show Details

Synaptic Pharmaceutical Corporation

Patent: US2003/166066 A1, 2003 ; Title/Abstract Full Text Show Details

May, Jesse A.; Dean, Thomas R.; Sharif, Najam A.; Hellberg, Mark R.

Patent: US2003/203912 A1, 2003 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US6667303 B1, 2003 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US2004/9970 A1, 2004 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US2004/19040 A1, 2004 ; Title/Abstract Full Text Show Details

ALCON, INC.

Patent: WO2004/19874 A2, 2004 ;

Title/Abstract Full Text Show Details

AMERICAN HOME PRODUCTS CORPORATION

Patent: WO2000/35922 A1, 2000 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2003/91257 A1, 2003 ; Title/Abstract Full Text Show Details

WYETH A CORPORATION OF THE STATE OF DELAWARE

Patent: WO2005/44812 A1, 2005 ; Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US2005/261347 A1, 2005 ; Title/Abstract Full Text Show Details

TAKEDA PHARMACEUTICAL COMPANY LIMITED

Patent: WO2006/22420 A1, 2006 ; Title/Abstract Full Text Show Details

2 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

UNIVERSIDADE FEDERAL DO RIO DE JANEIRO-UFRJ; UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL-UFRGS

Patent: WO2006/24121 A1, 2006 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US2006/94752 A1, 2006 ; Title/Abstract Full Text Show Details

JANSSEN PHARMACEUTICA N.V.

Patent: WO2006/76741 A2, 2006 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US2006/247276 A1, 2006 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2006/116170 A1, 2006 ; Title/Abstract Full Text Show Details

Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.

Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details

Takeda Pharmaceutical Company Limited

Patent: EP1792629 A1, 2007 ; Title/Abstract Full Text Show Details

Braun et al.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 1543 Full Text View citing articles Show Details

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon

Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details

Goodman; Kabalka; Marks; Knapp Jr.; Lee; Liang

Journal of Medicinal Chemistry, 1992 , vol. 35, # 2 p. 280 - 285 Title/Abstract Full Text View citing articles Show Details

Macor; Fox; Johnson; Koe; Lebel; Zorn

Journal of Medicinal Chemistry, 1992 , vol. 35, # 20 p. 3625 - 3632 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

Glennon; Young; Benington; Morin

Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details

Tetrahedron Letters, 1993 , vol. 34, # 39 p. 6223 - 6224 Title/Abstract Full Text View citing articles Show Details

Dawson, Brian A.; Black, D. B.; Sy, W.-W.; Graham, K.

Magnetic Resonance in Chemistry, 1994 , vol. 32, # 9 p. 557 - 558 Title/Abstract Full Text Show Details

Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4346 - 4351 Title/Abstract Full Text View citing articles Show Details

Parker, Matthew A.; Marona-Lewicka, Danuta; Kurrasch, Deborah; Shulgin, Alexander T.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 6 p. 1001 - 1005 Title/Abstract Full Text View citing articles Show Details

Clare, Brian W.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 20 p. 3845 - 3856 Title/Abstract Full Text View citing articles Show Details

Le Grand; Talmant; Rieu; Patoiseau; Colpaert; John

Journal of Cardiovascular Pharmacology, 1995 , vol. 26, # 5 p. 803 - 809 Title/Abstract Full Text View citing articles Show Details

Sanchez

Pharmacology and Toxicology, 1995 , vol. 77, # 1 p. 71 - 78 Title/Abstract Full Text View citing articles Show Details

3 of 174

4 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Yamada; Sugimoto; Horisaka

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 11 p. 1580 - 1583 Title/Abstract Full Text View citing articles Show Details

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.

Medicinal Chemistry Research, 1995 , vol. 5, # 9 p. 651 - 663 Title/Abstract Full Text Show Details

Garnovskaya; Nebigil; Arthur; Spurney; Raymond

Molecular Pharmacology, 1995 , vol. 48, # 2 p. 230 - 237 Title/Abstract Full Text View citing articles Show Details

Mundey; Fletcher; Marsden

British Journal of Pharmacology, 1996 , vol. 117, # 4 p. 750 - 756 Title/Abstract Full Text View citing articles Show Details

Padoin; Lucion

European Journal of Pharmacology, 1995 , vol. 277, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Parker, Matthew A.; Marona-Lewicka, Danuta; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 26 p. 5148 - 5149 Title/Abstract Full Text View citing articles Show Details

Blair, Joseph B.; Marona-Lewicka, Danuta; Kanthasamy, Arthi; Lucaites, Virginia L.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1999 , vol. 42, # 6 p. 1106 - 1111 Title/Abstract Full Text View citing articles Show Details

Nankai; Yamada; Muneoka; Toru

European Journal of Pharmacology, 1995 , vol. 281, # 2 p. 123 - 130 Title/Abstract Full Text View citing articles Show Details

Schreiber; Brocco; Audinot; Gobert; Veiga; Millan

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 273, # 1 p. 101 - 112 Title/Abstract Full Text View citing articles Show Details

Eison; Freeman; Cuss; Mullins; Wright

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 273, # 1 p. 304 - 308 Title/Abstract Full Text View citing articles Show Details

Ullmer; Boddeke; Schmuck; Lubbert

British Journal of Pharmacology, 1996 , vol. 117, # 6 p. 1081 - 1088 Title/Abstract Full Text View citing articles Show Details

Shi Wei-Xing; Nathaniel; Bunney

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 2 p. 735 - 740 Title/Abstract Full Text View citing articles Show Details

Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.

Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.

Molecular Pharmacology, 1996 , vol. 50, # 1 p. 34 - 42 Title/Abstract Full Text View citing articles Show Details

Chen; Li; Chuang

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 2 p. 674 - 680 Title/Abstract Full Text View citing articles Show Details

Sleight, Andrew J.; Stam, Nico J.; Mutel, Vincent; Vanderheyden, Patrick M. L.

Biochemical Pharmacology, 1996 , vol. 51, # 1 p. 71 - 76 Title/Abstract Full Text View citing articles Show Details

Hillegaart; Estival; Ahlenius

European Journal of Pharmacology, 1996 , vol. 295, # 2-3 p. 155 - 161 Title/Abstract Full Text View citing articles Show Details

Zethof, Theo J. J.; Van der Heyden, Jan A. M.; Tolboom, Jeroen T. B. M.; Olivier, Berend

European Journal of Pharmacology, 1995 , vol. 294, # 1 p. 125 - 136 Title/Abstract Full Text View citing articles Show Details

Wadenberg; Ahlenius

European Journal of Pharmacology, 1995 , vol. 294, # 1 p. 247 - 251 Title/Abstract Full Text View citing articles Show Details

Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols

Journal of Medicinal Chemistry, 2000 , vol. 43, # 24 p. 4701 - 4710 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Sugimoto, Yumi; Yamada, Jun; Yoshikawa, Tomoko; Horisaka, Kazuyoshi

European Journal of Pharmacology, 1996 , vol. 307, # 1 p. 75 - 80 Title/Abstract Full Text View citing articles Show Details

Berendsen, Hemmie H.G.; Kester, Robert C.H.; Peeters, Bernard W.M.M.; Broekkamp, Chris L.E.

European Journal of Pharmacology, 1996 , vol. 308, # 2 p. 103 - 111 Title/Abstract Full Text View citing articles Show Details

Zgombick, John M.; Schechter, Lee E.; Adham, Nika; Kucharewicz, Stefan A.; Weinshank, Richard L.; Branchek, Theresa A.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 3 p. 226 - 236 Title/Abstract Full Text View citing articles Show Details

Roth; Palvimaki; Berry; Khan; Sachs; Uluer; Choudhary

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 3 p. 1638 - 1646 Title/Abstract Full Text View citing articles Show Details

Pauwels, Petrus J.; Wurch, Thierry; Palmier, Christiane; Colpaert, Francis C.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 2 p. 136 - 144 Title/Abstract Full Text View citing articles Show Details

Laban, Uros; Kurrasch-Orbaugh, Deborah; Marona-Lewicka, Danuta; E. Nichols, David

Bioorganic and Medicinal Chemistry Letters, 2001 , vol. 11, # 6 p. 793 - 795 Title/Abstract Full Text View citing articles Show Details

Odagaki; Fuxe

European Journal of Pharmacology - Molecular Pharmacology Section, 1995 , vol. 288, # 3 p. 385 - 388 Title/Abstract Full Text View citing articles Show Details

Centurion, David; Ortiz, Mario I; Sanchez-Lopez, Araceli; De Vries, Peter; Saxena, Pramod R; Villalon, Carlos M

British Journal of Pharmacology, 2001 , vol. 132, # 5 p. 983 - 990 Title/Abstract Full Text View citing articles Show Details

Krebs-Thomson, Kirsten; Lehmann-Masten, Virginia; Naiem, Shahrouz; Paulus, Martin P.; Geyer, Mark A.

European Journal of Pharmacology, 1998 , vol. 343, # 2-3 p. 135 - 143 Title/Abstract Full Text View citing articles Show Details

Wurch, Thierry; Palmier, Christiane; Pauwels, Petrus J.

Biochemical Pharmacology, 2000 , vol. 59, # 9 p. 1117 - 1121 Title/Abstract Full Text View citing articles Show Details

Alberts, Glen L.; Chio, Christopher L.; Im, Wha Bin; Slightom, Jerry L.

British Journal of Pharmacology, 2003 , vol. 138, # 3 p. 427 - 434 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.

Journal of Medicinal Chemistry, 2003 , vol. 46, # 14 p. 2795 - 2812 Title/Abstract Full Text View citing articles Show Details

Cussac, Didier; Newman-Tancredi, Adrian; Quentric, Yann; Carpentier, Nathalie; Poissonnet, Guillaume; Parmentier, JeanGilles; Goldstein, Solo; Millan, Mark J.

Naunyn-Schmiedeberg's Archives of Pharmacology, 2002 , vol. 365, # 3 p. 242 - 252 Title/Abstract Full Text View citing articles Show Details

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

May, Jesse A.; Chen, Hwang-Hsing; Rusinko, Andrew; Lynch, Vincent M.; Sharif, Najam A.; McLaughlin, Marsha A.

Journal of Medicinal Chemistry, 2003 , vol. 46, # 19 p. 4188 - 4195 Title/Abstract Full Text View citing articles Show Details

Tian, Run-Xian; Kimura, Shoji; Kondou, Naoki; Fujisawa, Yoshihide; Zhou, Ming-Sheng; Yoneyama, Hirohito; Kosaka, Hiroaki; Rahman, Matlubur; Nishiyama, Akira; Abe, Youichi

European journal of pharmacology, 2002 , vol. 437, # 1-2 p. 79 - 84 Title/Abstract Full Text View citing articles Show Details

Willins, David L.; Meltzer, Herbert Y.

Journal of Pharmacology and Experimental Therapeutics, 1997 , vol. 282, # 2 p. 699 - 706 Title/Abstract Full Text View citing articles Show Details

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Marek, Gerard J.; Aghajanian, George K.

Journal of Pharmacology and Experimental Therapeutics, 1996 , vol. 278, # 3 p. 1373 - 1382 Title/Abstract Full Text View citing articles Show Details

Waeber; Moskowitz

Molecular pharmacology, 1997 , vol. 52, # 4 p. 623 - 631 Title/Abstract Full Text View citing articles Show Details

5 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Locher, Christopher P.; Ruben, Peter C.; Gut, Jiri; Rosenthal, Philip J.

Antimicrobial Agents and Chemotherapy, 2003 , vol. 47, # 12 p. 3806 - 3809 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A.

Journal of Medicinal Chemistry, 2004 , vol. 47, # 24 p. 6034 - 6041 Title/Abstract Full Text View citing articles Show Details

Guang, Wei; Wang, Hongyan; Su, Tao; Weinstein, I. Bernard; Jia, Bei Wang

Molecular Pharmacology, 2004 , vol. 66, # 5 p. 1285 - 1292 Title/Abstract Full Text View citing articles Show Details

Martin; Boes; Jenck; Moreau; Mutel; Sleight; Wichmann; Andrews; Berendsen; Broekkamp; Ruigt; Koehler; Delft

The Journal of pharmacology and experimental therapeutics, 1998 , vol. 286, # 2 p. 913 - 924 Title/Abstract Full Text View citing articles Show Details

Thakur, Mamta; Thakur, Abhilash; Khadikar, Padmakar V.

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 4 p. 825 - 831 Title/Abstract Full Text View citing articles Show Details

Dunlop, John; Sabb, Annmarie L.; Mazandarani, Hossein; Zhang, Jean; Kalgaonker, Sachin; Shukhina, Eugenia; Sukoff, Stacey; Vogel, Robert L.; Stack, Gary; Schechter, Lee; Harrison, Boyd L.; Rosenzweig-Lipson, Sharon

Journal of Pharmacology and Experimental Therapeutics, 2005 , vol. 313, # 2 p. 862 - 869 Title/Abstract Full Text View citing articles Show Details

Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Helmeste, Daiga M.; Tang, Siu W.; Li, Ming; Fang, Hong

Naunyn-Schmiedeberg's Archives of Pharmacology, 1997 , vol. 356, # 1 p. 17 - 21 Title/Abstract Full Text View citing articles Show Details

Zhang, Jean Y.; Kowal, Dianne M.; Nawoschik, Stanley P.; Lou, Zhuangwei; Dunlop, John

Biochemical Pharmacology, 2006 , vol. 71, # 4 p. 521 - 529 Title/Abstract Full Text View citing articles Show Details

Sugimoto; Yamada

Biological and pharmaceutical bulletin, 2000 , vol. 23, # 12 p. 1521 - 1523 Title/Abstract Full Text View citing articles Show Details

Peng, Wen-Huang; Wu, Chi-Rei; Chen, Chia-Sheng; Chen, Chung-Fung; Leu, Zong-Chung; Hsieh, Ming-Tsuen

Life Sciences, 2004 , vol. 75, # 20 p. 2451 - 2462 Title/Abstract Full Text View citing articles Show Details

Knight, Antony R.; Misra, Anil; Quirk, Kathleen; Benwell, Karen; Revell, Dean; Kennett, Guy; Bickerdike, Mike

Naunyn-Schmiedeberg's Archives of Pharmacology, 2004 , vol. 370, # 2 p. 114 - 123 Title/Abstract Full Text View citing articles Show Details

Nilsson, Bjoern M.

Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4023 - 4034 Title/Abstract Full Text View citing articles Show Details

Braden, Michael R.; Parrish, Jason C.; Naylor, John C.; Nichols, David E.

Molecular Pharmacology, 2006 , vol. 70, # 6 p. 1956 - 1964 Title/Abstract Full Text View citing articles Show Details

Bunzow; Sonders; Arttamangkul; Harrison; Zhang; Quigley; Darland; Suchland; Pasumamula; Kennedy; Olson; Magenis; Amara; Grandy

Molecular Pharmacology, 2001 , vol. 60, # 6 p. 1181 - 1188 Title/Abstract Full Text View citing articles Show Details

Shapiro, David A.; Kristiansen, Kurt; Kroeze, Wesley K.; Roth, Bryan L.

Molecular Pharmacology, 2000 , vol. 58, # 5 p. 877 - 886 Title/Abstract Full Text View citing articles Show Details

McLean, Thomas H.; Parrish, Jason C.; Braden, Michael R.; Marona-Lewicka, Danuta; Gallardo-Godoy, Alejandra; Nichols, David E.

Journal of Medicinal Chemistry, 2006 , vol. 49, # 19 p. 5794 - 5803 Title/Abstract Full Text View citing articles Show Details

Marquis, Karen L.; Sabb, Annmarie L.; Logue, Sheree F.; Brennan, Julie A.; Piesla, Michael J.; Comery, Tom A.; Grauer, Steven M.; Ashby Jr., Charles R.; Nguyen, Huy Q.; Dawson, Lee A.; Barrett, James E.; Stack, Gary; Meltzer, Herbert Y.; Harrison, Boyd L.; Rosenzweig-Lipson, Sharon

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 320, # 1 p. 486 - 496 Title/Abstract Full Text View citing articles Show Details

6 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Fantegrossi, William E.; Murnane, Kevin S.; Reissig, Chad J.

Biochemical Pharmacology, 2008 , vol. 75, # 1 p. 17 - 33 Title/Abstract Full Text View citing articles Show Details

Qiu, Jian; Xue, Changhui; Bosch, Martha A.; Murphy, Jonathan G.; Fan, Wei; Ronnekleiv, Oline K.; Kelly, Martin J.

Molecular Pharmacology, 2007 , vol. 72, # 4 p. 885 - 896 Title/Abstract Full Text View citing articles Show Details

Board of Supervisors of Louisiana State University; Agricultural and Mechanical College

Patent: US5417987 A1, 1995 ; Title/Abstract Full Text Show Details

American Home Products Corporation

Patent: US2002/86860 A1, 2002 ; Title/Abstract Full Text Show Details

Washington University

Patent: US5902815 A1, 1999 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2008/52075 A2, 2008 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2008/52078 A2, 2008 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2008/52086 A1, 2008 ; Title/Abstract Full Text Show Details

AUSPEX PHARMACEUTICALS, INC.

Patent: US2008/280991 A1, 2008 ;

Title/Abstract Full Text Show Details

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 8 p. 4661 - 4669 Title/Abstract Full Text View citing articles Show Details

Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details

Werry, Tim D.; Stewart, Gregory D.; Crouch, Michael F.; Watts, Anne; Sexton, Patrick M.; Christopoulos, Arthur

Biochemical Pharmacology, 2008 , vol. 76, # 10 p. 1276 - 1287 Title/Abstract Full Text View citing articles Show Details

MOUNT SINAI SCHOOL OF MEDICINE OF NEW YORK UNIVERSITY

Patent: WO2009/100384 A2, 2009 ; Title/Abstract Full Text Show Details

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.

Journal of Medicinal Chemistry, 2008 , vol. 51, # 21 p. 6808 - 6828 Title/Abstract Full Text View citing articles Show Details

ALCON, INC.

Patent: WO2004/54572 A2, 2004 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2005/40146 A1, 2005 ; Title/Abstract Full Text Show Details

WYETH

Patent: WO2006/116165 A1, 2006 ; Title/Abstract Full Text Show Details

Wyeth

Patent: US2006/241172 A1, 2006 ; Title/Abstract Full Text Show Details

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

7 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Hong, Sang-Phyo; Liu, Kevin G.; Ma, Gil; Sabio, Michael; Uberti, Michelle A.; Bacolod, Maria D.; Peterson, John; Zou, Zack Z.; Robichaud, Albert J.; Doller, Dario

Journal of Medicinal Chemistry, 2011 , vol. 54, # 14 p. 5070 - 5081 Title/Abstract Full Text View citing articles Show Details

Dolusic, Eduard; Larrieu, Pierre; Moineaux, Laurence; Stroobant, Vincent; Pilotte, Luc; Colau, Didier; Pochet, Lionel; Van Den Eynde, Benoit; Masereel, Bernard; Wouters, Johan; Frederick, Raphael

Journal of Medicinal Chemistry, 2011 , vol. 54, # 15 p. 5320 - 5334 Title/Abstract Full Text View citing articles Show Details

Andres, Jose-Ignacio; De Angelis, Meri; Alcazar, Jesus; Iturrino, Laura; Langlois, Xavier; Dedeurwaerdere, Stefanie; Lenaerts, Ilse; Vanhoof, Greet; Celen, Sofie; Bormans, Guy

Journal of Medicinal Chemistry, 2011 , vol. 54, # 16 p. 5820 - 5835 Title/Abstract Full Text View citing articles Show Details

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Parrish, Jason C.; Braden, Michael R.; Gundy, Emily; Nichols, David E.

Journal of Neurochemistry, 2005 , vol. 95, # 6 p. 1575 - 1584 Title/Abstract Full Text View citing articles Show Details

Blaazer, Antoni R.; Smid, Pieter; Kruse, Chris G.

ChemMedChem, 2008 , vol. 3, # 9 p. 1299 - 1309 Title/Abstract Full Text View citing articles Show Details

Huang, Xi-Ping; Setola, Vincent; Yadav, Prem N.; Allen, John A.; Rogan, Sarah C.; Hanson, Bonnie J.; Revankar, Chetana; Robers, Matt; Doucette, Chris; Roth, Bryan L.

Molecular Pharmacology, 2009 , vol. 76, # 4 p. 710 - 722 Title/Abstract Full Text View citing articles Show Details

Knutson, Sarah K.; Wigle, Tim J.; Warholic, Natalie M.; Sneeringer, Christopher J.; Allain, Christina J.; Klaus, Christine R.; Sacks, Joelle D.; Raimondi, Alejandra; Majer, Christina R.; Song, Jeffrey; Scott, Margaret Porter; Jin, Lei; Smith, Jesse J.; Olhava, Edward J.; Chesworth, Richard; Moyer, Mikel P.; Richon, Victoria M.; Copeland, Robert A.; Keilhack, Heike; Pollock, Roy M.; Kuntz, Kevin W.

Nature Chemical Biology, 2012 , vol. 8, # 11 p. 890 - 896 Title/Abstract Full Text View citing articles Show Details

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Veinberg, Grigory; Vorona, Maxim; Zvejniece, Liga; Vilskersts, Reinis; Vavers, Edijs; Liepinsh, Edvards; Kazoka, Helena; Belyakov, Sergey; Mishnev, Anatoly; Kuznecovs, Jevgenijs; Vikainis, Sergejs; Orlova, Natalja; Lebedev, Anton; Ponomaryov, Yuri; Dambrova, Maija

Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 10 p. 2764 - 2771 Title/Abstract Full Text View citing articles Show Details

Braun; Shulgin; Sargent III

Journal of Medicinal Chemistry, 1977 , vol. 20, # 12 p. 1543 - 1546 Title/Abstract Full Text Show Details

Leysen

Current drug targets. CNS and neurological disorders, 2004 , vol. 3, # 1 p. 11 - 26 Title/Abstract Full Text Show Details

Slawinska, Anna; Wieronska, Joanna M.; Stachowicz, Katarzyna; Marciniak, Marcin; Lason-Tyburkiewicz, Magdalena; Gruca, Piotr; Papp, Mariusz; Kusek, Magdalena; Tokarski, Krzysztof; Doller, Dario; Pilc, Andrzej

British Journal of Pharmacology, 2013 , vol. 169, # 8 p. 1824 - 1839 Title/Abstract Full Text View citing articles Show Details

Menzaghi, Frederique; Behan, Dominic P; Chalmers, Derek T

Current drug targets. CNS and neurological disorders, 2002 , vol. 1, # 1 p. 105 - 121 Title/Abstract Full Text View citing articles Show Details

Wellendorph; Goodman; Burstein; Nash; Brann; Weiner

Neuropharmacology, 2002 , vol. 42, # 7 p. 929 - 940 Title/Abstract Full Text View citing articles Show Details

Shapiro, David A.; Kristiansen, Kurt; Weiner, David M.; Kroeze, Wesley K.; Roth, Bryan L.

Journal of Biological Chemistry, 2002 , vol. 277, # 13 p. 11441 - 11449 Title/Abstract Full Text View citing articles Show Details

Ebersole, Barbara J.; Weinstein, Harel; Sealfon, Stuart C.

Journal of Biological Chemistry, 2002 , vol. 277, # 39 p. 36577 - 36584 Title/Abstract Full Text View citing articles Show Details

Black; Simmonds; Senyah; Wettstein

Neuropharmacology, 2002 , vol. 42, # 3 p. 414 - 420 Title/Abstract Full Text View citing articles Show Details

Tian, Run-Xian; Kimura, Shoji; Kondou, Naoki; Fujisawa, Yoshihide; Zhou, Ming-Sheng; Yoneyama, Hirohito; Kosaka, Hiroaki; Rahman, Matlubur; Nishiyama, Akira; Abe, Youichi

European Journal of Pharmacology, 2002 , vol. 437, # 1-2 p. 79 - 84 Title/Abstract Full Text View citing articles Show Details

Westkaemper, Richard B; Glennon, Richard A

Current topics in medicinal chemistry, 2002 , vol. 2, # 6 p. 575 - 598 Title/Abstract Full Text View citing articles Show Details

8 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Sugimoto; Yamada

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 12 p. 1521 - 1523 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; Dukat, Malgorzata; Grella, Brian; Hong, Seoung-Soo; Costantino, Luca; Teitler, Milt; Smith, Carol; Egan, Chris; Davis, Katherine; Mattson, Mariena V.

Drug and Alcohol Dependence, 2000 , vol. 60, # 2 p. 121 - 132 Title/Abstract Full Text View citing articles Show Details

Rosendorff, Adam; Ebersole, Barbara J.; Sealfon, Stuart C.

Molecular Brain Research, 2000 , vol. 84, # 1-2 p. 90 - 96 Title/Abstract Full Text View citing articles Show Details

Niswender, Colleen M.; Copeland, Sara C.; Herrick-Davis, Katharine; Emeson, Ronald B.; Sanders-Bush, Elaine

Journal of Biological Chemistry, 1999 , vol. 274, # 14 p. 9472 - 9478 Title/Abstract Full Text View citing articles Show Details

Waeber, Christian; Moskowitz, Michael A.

Molecular Pharmacology, 1997 , vol. 52, # 4 p. 623 - 631 Title/Abstract Full Text View citing articles Show Details

Marek; Aghajanian

Journal of Pharmacology and Experimental Therapeutics, 1996 , vol. 278, # 3 p. 1373 - 1382 Title/Abstract Full Text View citing articles Show Details

Roth, Bryan L.; Choudhary; Khan; Uluer

Journal of Pharmacology and Experimental Therapeutics, 1997 , vol. 280, # 2 p. 576 - 583 Title/Abstract Full Text View citing articles Show Details

Zethof; Van Der Heyden; Tolboom; Olivier

European Journal of Pharmacology, 1995 , vol. 294, # 1 p. 125 - 135 Title/Abstract Full Text Show Details

Sleight; Stam; Mutel; Vanderheyden

Biochemical Pharmacology, 1996 , vol. 51, # 1 p. 71 - 76 Title/Abstract Full Text Show Details

Munday; Fletcher; Marsden

British Journal of Pharmacology, 1996 , vol. 117, # 4 p. 750 - 756 Title/Abstract Full Text Show Details

Ullmer; Boddeke; Schmuck; Lubbert

British Journal of Pharmacology, 1996 , vol. 117, # 6 p. 1081 - 1088 Title/Abstract Full Text Show Details

Nichols; Frescas; Marona-Lewicka; Huang; Roth; Gudelsky; Nash

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4346 - 4351 Title/Abstract Full Text Show Details

Shi; Nathaniel; Bunney

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 2 p. 735 - 740 Title/Abstract Full Text View citing articles Show Details

Garnovskaya; Nebigil; Arthur; Spurney; Raymond

Molecular Pharmacology, 1995 , vol. 48, # 2 p. 230 - 237 Title/Abstract Full Text Show Details

Sealfon; Chi; Ebersole; Rodic; Zhang; Ballesteros; Weinstein

Journal of Biological Chemistry, 1995 , vol. 270, # 28 p. 16683 - 16688 Title/Abstract Full Text Show Details

Johnson, Michael P.; Loncharich, Richard J.; Baez, Melvyn; Nelson, David L.

Molecular Pharmacology, 1994 , vol. 45, # 2 p. 277 - 286 Title/Abstract Full Text View citing articles Show Details

Schmuck; Ullmer; Engels; Lubbert

FEBS Letters, 1994 , vol. 342, # 1 p. 85 - 90 Title/Abstract Full Text Show Details

Schoeffter; Waeber

Naunyn-Schmiedeberg's Archives of Pharmacology, 1994 , vol. 350, # 4 p. 356 - 360 Title/Abstract Full Text Show Details

De Vry; Benz; Schreiber; Traber

European Journal of Pharmacology, 1993 , vol. 249, # 3 p. 331 - 339 Title/Abstract Full Text Show Details

Becker; Gettys; Middleton; Olsen; Albers; Lee -; Fanburg; Raymond

Molecular Pharmacology, 1992 , vol. 42, # 5 p. 817 - 825 Title/Abstract Full Text Show Details

9 of 174

10 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Zgombick; Schechter; Macchi; Hartig; Branchek; Weinshank

Molecular Pharmacology, 1992 , vol. 42, # 2 p. 180 - 185 Title/Abstract Full Text Show Details

Leonhardt; Gorospe; Hoffman; Teitler

Molecular Pharmacology, 1992 , vol. 42, # 2 p. 328 - 335 Title/Abstract Full Text Show Details

Adham; Kao; Schechter; Bard; Olsen; Urquhart; Durkin; Hartig; Weinshank; Branchek

Proceedings of the National Academy of Sciences of the United States of America, 1993 , vol. 90, # 2 p. 408 - 412 Title/Abstract Full Text Show Details

Wainscott; Cohen; Schenck; Audia; Nissen; Baez; Kursar; Lucaites; Nelson

Molecular Pharmacology, 1993 , vol. 43, # 3 p. 419 - 426 Title/Abstract Full Text Show Details

Wang; Gallaher; Shih

Molecular Pharmacology, 1993 , vol. 43, # 6 p. 931 - 940 Title/Abstract Full Text Show Details

Johnson; Audia; Nissen; Nelson

European Journal of Pharmacology, 1993 , vol. 239, # 1-3 p. 111 - 118 Title/Abstract Full Text Show Details

Choudhary; Craigo; Roth

Molecular Pharmacology, 1993 , vol. 43, # 5 p. 755 - 761 Title/Abstract Full Text Show Details

Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text Show Details

Zgombick; Weinshank; Macchi; Schechter; Branchek; Hartig

Molecular Pharmacology, 1991 , vol. 40, # 6 p. 1036 - 1042 Title/Abstract Full Text Show Details

Demchyshyn; Sunahara; Miller; Teitler; Hoffman; Kennedy; Seeman; Van Tol; Niznik

Proceedings of the National Academy of Sciences of the United States of America, 1992 , vol. 89, # 12 p. 5522 - 5526 Title/Abstract Full Text Show Details

Ivins; Molinoff

Molecular Pharmacology, 1990 , vol. 37, # 5 p. 622 - 630 Title/Abstract Full Text View citing articles Show Details

Van Wijngaarden; Tulp; Soudijn

European Journal of Pharmacology - Molecular Pharmacology Section, 1990 , vol. 188, # 6 p. 301 - 312 Title/Abstract Full Text Show Details

Berendsen; Jenck; Broekkamp

Pharmacology, biochemistry, and behavior, 1989 , vol. 33, # 4 p. 821 - 827 Title/Abstract Full Text Show Details

Britt; Gonias; Sanders; Vandenberg

Journal of Pharmacology and Experimental Therapeutics, 1988 , vol. 247, # 3 p. 965 - 970 Title/Abstract Full Text View citing articles Show Details

Hoyer; Waeber; Schoeffter; Palacios; Dravid

Naunyn-Schmiedeberg's archives of pharmacology, 1989 , vol. 339, # 3 p. 252 - 258 Title/Abstract Full Text Show Details

Hoyer; Karpf

European journal of pharmacology, 1988 , vol. 150, # 1-2 p. 181 - 184 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

Psychopharmacology, 1988 , vol. 94, # 2 p. 213 - 216 Title/Abstract Full Text Show Details

Hoyer

Trends in Pharmacological Sciences, 1988 , vol. 9, # 3 p. 89 - 94 Title/Abstract Full Text Show Details

Glennon; Seggel; Soine; Herrick-Davis; Lyon; Titeler

Journal of medicinal chemistry, 1988 , vol. 31, # 1 p. 5 - 7 Title/Abstract Full Text Show Details

Glennon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 1 - 12 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Glennon; McKenney; Lyon; Titeler

Journal of medicinal chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text Show Details

Sargent III; Shulgin; Mathis

Journal of Medicinal Chemistry, 1984 , vol. 27, # 8 p. 1071 - 1077 Title/Abstract Full Text Show Details

Shannon; Battaglia; Glennon; Titeler

European journal of pharmacology, 1984 , vol. 102, # 1 p. 23 - 29 Title/Abstract Full Text Show Details

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero

Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details

Unett, David J.; Gatlin, Joel; Anthony, Todd L.; Buzard, Daniel J.; Chang, Steve; Chen, Chuan; Chen, Xiaohua; Dang, Huong T.-M.; Frazer, John; Le, Minh K.; Sadeque, Abu J.M.; Xing, Charles; Gaidarov, Ibragim

Journal of Pharmacology and Experimental Therapeutics, 2013 , vol. 347, # 3 p. 645 - 659 Title/Abstract Full Text View citing articles Show Details

Bard, Jonathan A.; Branchek, Theresa; Weinshank, Richard L.

Patent: US2003/166066 A1, 2003 ; Title/Abstract Full Text Show Details

Weinshank; Richard L.; Branchek; Theresa; Hartig; Paul R.

Patent: US6475746 , 2002 ; Title/Abstract Full Text Show Details

Weinshank; Richard L.; Branchek; Theresa; Hartig; Paul R.

Patent: US6406859 , 2002 ; Title/Abstract Full Text Show Details

McConnell; Bruce; Locher; Christopher P.

Patent: US5874477 , 1999 ; Title/Abstract Full Text Show Details

Sabb, Annmarie Louise; Vogel, Robert Lewis; Nelson, James Albert; Rosenzweig-Lipson, Sharon Joy; Welmaker, Gregory Scott; Sabalski, Joan Eileen; Smith, Michael David; Chan, Anita Wai-Yin; Antane, Madelene Miyoko; Raveendranath, Panolil; Megati, Sreenivasulu.

Patent: WO2002/42304 , 2002 ; Title/Abstract Full Text Show Details

James E. Audia; Marlene L. Cohen

Annual reports in medicinal chemistry, 1991 , vol. 26, p. 103 - 112 Title/Abstract Full Text Show Details

Andrea Cappelli; Monica Manini; Salvatore Valenti; Federica Castriconi; Germano Giuliani; Maurizio Anzini; Simone Brogi; Stefania Butini; Sandra Gemma; Giuseppe Campiani; Gianluca Giorgi; Laura Mennuni; Marco Lanza; Antonio Giordani; Gianfranco Caselli; Ornella Letari; Francesco Makovec

European journal of medicinal chemistry, 2013 , vol. 63, p. 85 - 94 Title/Abstract Full Text Show Details

Richard L. Weinshank; Theresa Branchek; Paul R. Hartig

Patent: US5652113 A, 1997 ; Title/Abstract Full Text Show Details

Jonathan A. Bard; Theresa Branchek; Richard L. Weinshank

Patent: US5985585 A, 1999 ; Title/Abstract Full Text Show Details

Vani Munusamy; Beow Keat Yap; Michael J. C. Buckle; Stephen W. Doughty; Lip Yong Chung

Chemical biology & drug design, 2013 , vol. 81, # 2 p. 250 - 256 Title/Abstract Full Text Show Details

Zvejniece; Vavers; Svalbe; Vilskersts; Domracheva; Vorona; Veinberg; Misane; Stonans; Kalvinsh; Dambrova

British Journal of Pharmacology, 2014 , vol. 171, # 3 p. 761 - 771 Title/Abstract Full Text View citing articles Show Details

Partyka, Anna; Chlo-Rzepa, Grazyna; Wasik, Anna; Jastrzbska-Wisek, Magdalena; Bucki, Adam; Kolaczkowski, Marcin; Satala, Grzegorz; Bojarski, Andrzej J.; Wesolowska, Anna

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 1 p. 212 - 221 Title/Abstract Full Text View citing articles Show Details

Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; BräunerOsborne, Hans; Kristensen, Jesper Langgaard

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 14 p. 3933 - 3937 Title/Abstract Full Text View citing articles Show Details

Atack, John R.; Shook, Brian C.; Rassnick, Stefanie; Jackson, Paul F.; Rhodes, Kenneth; Drinkenburg, Wilhelmus H.; Ahnaou, Abdallah; Te Riele, Paula; Langlois, Xavier; Hrupka, Brian; De Haes, Patrick; Hendrickx, Herman; Aerts, Nancy; Hens, Koen; Wellens, Annemie; Vermeire, Jef; Megens, Anton A. H. P.

ACS Chemical Neuroscience, 2014 , vol. 5, # 10 p. 1005 - 1019 Title/Abstract Full Text View citing articles Show Details

INTRA-CELLULAR THERAPIES, INC.; VANOVER, Kimberly; LI, Peng; MATES, Sharon; DAVIS, Robert; WENNOGLE, Lawrence P.

Patent: WO2015/85004 A1, 2015 ; Title/Abstract Full Text Show Details

11 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Waszkielewicz, Anna M.; Cegla, Marek; Zeslawska, Ewa; Nitek, Wojciech; Sloczyska, Karolina; Marona, Henryk

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 15 p. 4197 - 4217 Title/Abstract Full Text View citing articles Show Details

UNIVERSITÉ LAVAL; GUERTIN, Pierre

Patent: WO2015/127558 A1, 2015 ; Title/Abstract Full Text Show Details

UNIVERSITÉ LAVAL; GUERTIN, Pierre

Patent: WO2015/127556 A1, 2015 ;

Title/Abstract Full Text Show Details

NORTHEASTERN UNIVERSITY; BOOTH, Raymond, G.

Patent: WO2015/179366 A1, 2015 ; Title/Abstract Full Text Show Details

CHAN Anita Wai-Yin; ANTANE Madelene Miyoko; RAVEENDRANATH Panolil; MEGATI Sreenivasulu; VOGEL Robert Lewis; NELSON James Albert; ROSENZWEIG-LIPSON Sharon Joy; SABALSKI Joan Eileen; SMITH Michael David; SABB Annmarie Louise; WELMAKER Gregory Scott

Patent: EP1330457 B1, 2004 ; Title/Abstract Full Text Show Details

Annmarie Louise Sabb; Robert Lewis Vogel; James Albert Nelson; Sharon Joy Rosenzweig-Lipson; Gregory Scott Welmaker; Joan Eileen Sabalski

Patent: US2005/4101 A1, 2005 ; Title/Abstract Full Text Show Details

Annmaire Louise Sabb; Robert Lewis Vogel

Patent: US2005/54635 A1, 2005 ; Title/Abstract Full Text Show Details

Annmarie Louise Sabb; Robert Lewis Vogel

Patent: US6759405 B2, 2004 ; Title/Abstract Full Text Show Details

Annmarie Louise Sabb; Robert Lewis Vogel; James Albert Nelson; Sharon Joy Rosenzweig-Lipson; Gregory Scott Welmaker; Joan Eileen Sabalski

Patent: US6777407 B2, 2004 ; Title/Abstract Full Text Show Details

SABB Annmarie Louise; VOGEL Robert Lewis; WELMAKER Gregory Scott; SABALSKI Joan Eileen

Patent: WO2002/36596 A2, 2002 ; Title/Abstract Full Text Show Details

Annmarie Louise Sabb; Gregory Scott Welmaker; Robert Lewis Vogel; Joan Eileen Sabalski

Patent: US6503900 B2, 2003 ; Title/Abstract Full Text Show Details

Hong Gao; Jonathan Laird Gross; Dahui Zhou; Gary Paul Stack; Gavin David Heffernan

Patent: US7365095 B2, 2008 ; Title/Abstract Full Text Show Details

WEINSHANK Richard L.; BRANCHEK Theresa; HARTIG Paul R.

Patent: EP530265 B1, 1998 ; Title/Abstract Full Text Show Details

BARD Jonathan A.; WEINSHANK Richard L.; BRANCHEK Theresa

Patent: EP624100 B1, 2000 ; Title/Abstract Full Text Show Details

Theresa Branchek; Paul R. Hartig; Richard L. Weinshank

Patent: US2002/115149 A1, 2002 ; Title/Abstract Full Text Show Details

Richard L. Weinshank; Theresa Brancheck; Paul R. Hartig

Patent: US2003/8823 A1, 2003 ; Title/Abstract Full Text Show Details

Annmarie Lousie Sabb; Gregory Scott Welmaker; James Albert Nelson

Patent: US2004/116437 A1, 2004 ; Title/Abstract Full Text Show Details

James Albert Nelson; Gregory Scott Welmaker; Annmarie Louise Sabb

Patent: US6706714 B2, 2004 ; Title/Abstract Full Text Show Details

SABB Annmarie Louise; VOGEL Robert Lewis

Patent: WO2006/50007 A2, 2006 ; Title/Abstract Full Text Show Details

HARTIG Paul R.; WEINSHANK Richard L.; BRANCHEK Theresa

Patent: WO1993/14201 A1, 1993 ; Title/Abstract Full Text Show Details

12 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

P. Sivaramakrishnan Ramamoorthy Patent: US7129237 B2, 2006 ; Title/Abstract Full Text Show Details

STACK Gary Paul; HUSELTON Christine; WANG Jianyao; DEMAIO William; JORDAN Ronald; ERVE John Chuck Lem; TALAAT Rasmy Elsayed; HOFFMAN Matthew John

Patent: WO2006/116150 A1, 2006 ;

Title/Abstract Full Text Show Details

GROSS Jonathan Laird; STACK Gary Paul; GAO Hong; ZHOU Dahui

Patent: WO2006/116151 A1, 2006 ; Title/Abstract Full Text Show Details

ZHOU Dahui; STACK Gary Paul; GAO Hong; GROSS Jonathan Laird

Patent: WO2006/116158 A1, 2006 ; Title/Abstract Full Text Show Details

Jiu Ai; Yanning Lin

Patent: US2006/258739 A1, 2006 ; Title/Abstract Full Text Show Details

The General Hospital Corporation; President and Fellows of Harvard College; Tilly, Jonathan Lee; Sinclair, David A

Patent: US2016/24527 A1, 2016 ; Title/Abstract Full Text Show Details

Bielenica, Anna; Kdzierska, Ewa; Koliski, Michal; Kmiecik, Sebastian; Koliski, Andrzej; Fiorino, Ferdinando; Severino, Beatrice; Magli, Elisa; Corvino, Angela; Rossi, Ilaria; Massarelli, Paola; Koziol, Anna E.; Sawczenko, Aleksandra; Struga, Marta

European Journal of Medicinal Chemistry, 2016 , vol. 116, p. 173 - 186 Title/Abstract Full Text View citing articles Show Details

Mori, Tomohisa; Uzawa, Naoki; Iwase, Yoshiyuki; Masukawa, Daiki; Rahmadi, Mahardian; Hirayama, Shigeto; Hokazono, Mayuna; Higashiyama, Kimio; Shioda, Seiji; Suzuki, Tsutomu

Psychopharmacology, 2016 , vol. 233, # 12 p. 2343 - 2353 Title/Abstract Full Text View citing articles Show Details

Robayo, Diego A. Snchez; Mendez, William F. Garzn; Ocampo, Gonzalo Taborda; Moreano, Milton Rosero

Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 6 p. 992 - 997 Title/Abstract Full Text View citing articles Show Details

Valle, Marta; Maqueda, Ana Elda; Rabella, Mireia; Rodríguez-Pujadas, Aina; Antonijoan, Rosa Maria; Romero, Sergio; Alonso, Joan Francesc; Mañanas, Miquel Àngel; Barker, Steven; Friedlander, Pablo; Feilding, Amanda; Riba, Jordi

European Neuropsychopharmacology, 2016 , vol. 26, # 7 p. 1161 - 1175 Title/Abstract Full Text View citing articles Show Details

Christensen, Desiré K.; Armaiz-Pena, Guillermo N.; Ramirez, Edgardo; Matsuo, Koji; Zimmerman, Bridget; Zand, Behrouz; Shinn, Eileen; Goodheart, Michael J.; Bender, David; Thaker, Premal H.; Ahmed, Amina; Penedo, Frank J.; DeGeest, Koen; Mendez, Luis; Domann, Frederick; Sood, Anil K.; Lutgendorf, Susan K.

Oncotarget, 2016 , vol. 7, # 22 p. 33179 - 33191 Title/Abstract Full Text View citing articles Show Details

Monti, Jaime M.; Torterolo, Pablo; Pandi-Perumal, Seithikurippu R.

Clinical Medicine Insights: Therapeutics, 2016 , vol. 8, art. no. 3, p. 29 - 36 Title/Abstract Full Text View citing articles Show Details

Zhou, Jia; Ling, Jingjing; Ping, Fengfeng

Biological and Pharmaceutical Bulletin, 2016 , vol. 39, # 7 p. 1091 - 1099 Title/Abstract Full Text View citing articles Show Details

Malik, Maninder; Rangel-Barajas, Claudia; Mach, Robert H.; Luedtke, Robert R.

Pharmacology Biochemistry and Behavior, 2016 , vol. 148, p. 136 - 144 Title/Abstract Full Text View citing articles Show Details

Stefanowicz, Jacek; Słowiński, Tomasz; Wróbel, Martyna Zofia; Herold, Franciszek; Gomółka, Anna Edyta; Wesołowska, Anna; Jastrzębska-Więsek, Magdalena; Partyka, Anna; Andres-Mach, Marta; Czuczwar, Stanisław Jerzy; Łuszczki, Jarogniew Jacek; Zagaja, Mirosław; Siwek, Agata; Nowak, Gabriel; Żołnierek, Maria; Bączek, Tomasz; Ulenberg, Szymon; Belka, Mariusz; Turło, Jadwiga

Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 18 p. 3994 - 4007 Title/Abstract Full Text View citing articles Show Details

Hu, Lingli; Liu, Chunhua; Dang, Minyan; Luo, Bin; Guo, Yiping; Wang, Haitao

Neuroscience Letters, 2016 , vol. 632, p. 124 - 129 Title/Abstract Full Text Show Details

Glicksberg, Lindsay; Bryand, Kelsie; Kerrigan, Sarah

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 2016 , vol. 1035, p. 91 - 103 Title/Abstract Full Text Show Details

Fields; Mitchell

Neuropharmacology, 2017 , vol. 113, p. 82 - 88 Title/Abstract Full Text Show Details

Carbonaro, Theresa M.; Gatch, Michael B.

Brain Research Bulletin, 2016 , vol. 126, p. 74 - 88 Title/Abstract Full Text Show Details

Woźniak, Monika; Acher, Francine; Marciniak, Marcin; Łasoń-Tyburkiewicz, Magdalena; Gruca, Piotr; Papp, Mariusz; Pilc, Andrzej; Wierońska, Joanna M.

Current Neuropharmacology, 2016 , vol. 14, # 5 p. 413 - 426 Title/Abstract Full Text Show Details

13 of 174

14 of 174

Comment (Pharmacological Data)

Bioactivities present

Reference

Saz; Marina

Journal of Chromatography A, 2016 , vol. 1467, p. 79 - 94 Title/Abstract Full Text Show Details

Oliver, Kendra H.; Duvernay, Matthew T.; Hamm, Heidi E.; Carneiro, Ana M. D.

Journal of Biological Chemistry, 2016 , vol. 291, # 38 p. 20210 - 20219 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

15 of 174

Reference

Fields; Mitchell

Neuropharmacology, 2017 , vol. 113, p. 82 - 88 Title/Abstract Full Text Show Details

Location

Page/Page column

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

The General Hospital Corporation; President and Fellows of Harvard College; Tilly, Jonathan Lee; Sinclair, David A

Patent: US2016/24527 A1, 2016 ; Title/Abstract Full Text Show Details

16 of 174

17 of 174

18 of 174

19 of 174

20 of 174

21 of 174

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

European Journal of Medicinal Chemistry, 2016 , vol. 116, p. 173 - 186 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Mori, Tomohisa; Uzawa, Naoki; Iwase, Yoshiyuki; Masukawa, Daiki; Rahmadi, Mahardian; Hirayama, Shigeto; Hokazono, Mayuna; Higashiyama, Kimio; Shioda, Seiji; Suzuki, Tsutomu

Psychopharmacology, 2016 , vol. 233, # 12 p. 2343 - 2353 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Malik, Maninder; Rangel-Barajas, Claudia; Mach, Robert H.; Luedtke, Robert R.

Pharmacology Biochemistry and Behavior, 2016 , vol. 148, p. 136 - 144 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Partyka, Anna; Chlo-Rzepa, Grazyna; Wasik, Anna; Jastrzbska-Wisek, Magdalena; Bucki, Adam; Kolaczkowski, Marcin; Satala, Grzegorz; Bojarski, Andrzej J.; Wesolowska, Anna

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 1 p. 212 - 221 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Waszkielewicz, Anna M.; Cegla, Marek; Zeslawska, Ewa; Nitek, Wojciech; Sloczyska, Karolina; Marona, Henryk

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 15 p. 4197 - 4217 Title/Abstract Full Text View citing articles Show Details

Location

Paragraph

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

UNIVERSITÉ LAVAL; GUERTIN, Pierre

Patent: WO2015/127558 A1, 2015 ; Title/Abstract Full Text Show Details

22 of 174

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

UNIVERSITÉ LAVAL; GUERTIN, Pierre

Patent: WO2015/127556 A1, 2015 ; Title/Abstract Full Text Show Details

23 of 174

Comment (Pharmacological

physiological behaviour discussed

Data) Reference

NORTHEASTERN UNIVERSITY; BOOTH, Raymond, G.

Patent: WO2015/179366 A1, 2015 ; Title/Abstract Full Text Show Details

24 of 174

25 of 174

26 of 174

27 of 174

28 of 174

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Zvejniece; Vavers; Svalbe; Vilskersts; Domracheva; Vorona; Veinberg; Misane; Stonans; Kalvinsh; Dambrova

British Journal of Pharmacology, 2014 , vol. 171, # 3 p. 761 - 771 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

binding affinity

Species or TestSystem (Pharmacological Data)

not explicitly stated by authors

Method (Pharmacological Data)

name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

IC50 related to: serotonin 5-HT2B receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3.2 nmol/l

Reference

Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 10 p. 2764 - 2771 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

binding affinity

Species or TestSystem (Pharmacological Data)

not explicitly stated by authors

Method (Pharmacological Data)

name of assay/method: radioligand binding assay

Results

molecular target: serotonin 5-HT2B receptor; species of target: human

Reference

Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 10 p. 2764 - 2771 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

British Journal of Pharmacology, 2013 , vol. 169, # 8 p. 1824 - 1839 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Journal of Pharmacology and Experimental Therapeutics, 2013 , vol. 347, # 3 p. 645 - 659 Title/Abstract Full Text View citing articles Show Details

29 of 174

30 of 174

31 of 174

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

CHO cells; genetically modified/infected with: human recombinant 5-HT2B receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.2 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

Hill coefficient (nH); nH related to: 5-HT2B receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.8

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

CHO cells; genetically modified/infected with: human recombinant 5-HT2B receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.2 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

inhibition constant (Ki); Ki related to: 5-HT2B receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.3E-09 mol/l

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

CHO cells; genetically modified/infected with: human recombinant 5-HT2B receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.2 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

inhibitory concentration (IC); IC50 related to: 5-HT2B receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

6.6E-09 mol/l

32 of 174

33 of 174

34 of 174

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

CHO cells; genetically modified/infected with: human recombinant 5-HT2B receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.2 nmol/l); name of assay/method: radioligand binding assay

Results

molecular target: 5-HT2B receptor; species of target: human

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2A receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

Hill coefficient (nH); nH related to: 5-HT2A receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.6

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2A receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

inhibition constant (Ki); Ki related to: 5-HT2A receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

3.7E-10 mol/l

Location

supporting information

35 of 174

36 of 174

37 of 174

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2A receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

inhibitory concentration (IC); IC50 related to: 5-HT2A receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

5E-10 mol/l

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2A receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Results

molecular target: 5-HT2A receptor; species of target: human

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2C receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

Hill coefficient (nH); nH related to: 5-HT2C receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.9

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch,

Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

38 of 174

39 of 174

40 of 174

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2C receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

inhibition constant (Ki); Ki related to: 5-HT2C receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

5.9E-10 mol/l

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2C receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Further Details (Pharmacological Data)

inhibitory concentration (IC); IC50 related to: 5-HT2C receptor

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

6.6E-10 mol/l

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human recombinant 5-HT2C receptor

Method (Pharmacological Data)

labelled ligand: [125I](±)DOI (0.1 nmol/l); name of assay/method: radioligand binding assay

Results

molecular target: 5-HT2C receptor; species of target: human

Location

supporting information

Reference

Verheij, Mark H. P.; Thompson, Andrew J.; Van Muijlwijk-Koezen, Jacqueline E.; Lummis, Sarah C. R.; Leurs, Rob; De Esch, Iwan J. P.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 20 p. 8603 - 8614 Title/Abstract Full Text View citing articles Show Details

41 of 174

42 of 174

43 of 174

44 of 174

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

not explicitly stated by authors

Further Details (Pharmacological Data)

[125I](+/-)-DOI used as radioligand; Ki related to: serotonin h5-HT2B receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2 nmol/l

Reference

Dolusic, Eduard; Larrieu, Pierre; Moineaux, Laurence; Stroobant, Vincent; Pilotte, Luc; Colau, Didier; Pochet, Lionel; Van Den Eynde, Benoit; Masereel, Bernard; Wouters, Johan; Frederick, Raphael

Journal of Medicinal Chemistry, 2011 , vol. 54, # 15 p. 5320 - 5334 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

not explicitly stated by authors

Further Details (Pharmacological Data)

[125I](+/-)-DOI used as radioligand

Results

molecular target: serotonin h5-HT2B receptor

Reference

Dolusic, Eduard; Larrieu, Pierre; Moineaux, Laurence; Stroobant, Vincent; Pilotte, Luc; Colau, Didier; Pochet, Lionel; Van Den Eynde, Benoit; Masereel, Bernard; Wouters, Johan; Frederick, Raphael

Journal of Medicinal Chemistry, 2011 , vol. 54, # 15 p. 5320 - 5334 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ligand binding; inhibition of

Species or TestSystem (Pharmacological Data)

cortex homogenate of C57BL/6 mouse

Further Details (Pharmacological Data)

radioligand displacement assay; radioligand: 0.39 - 0.47 nM [3H]ketanserin

Results

molecular target: mouse serotonin 2A receptor

Reference

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ligand binding; inhibition of

Species or TestSystem (Pharmacological Data)

cortex homogenate of C57BL/6 mouse

Further Details (Pharmacological Data)

radioligand displacement assay; radioligand: 0.39 - 0.47 nM [3H]ketanserin; inhibition constant high affinity site (Ki (high)); Ki (high) related to: mouse serotonin 2A receptor

Type (Pharmacological Data)

Ki (high)

Value of Type

6.52 nmol/l

(Pharmacological Data)

45 of 174

46 of 174

47 of 174

Reference

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ligand binding; inhibition of

Species or TestSystem (Pharmacological Data)

cortex homogenate of C57BL/6 mouse

Further Details (Pharmacological Data)

radioligand displacement assay; radioligand: 0.39 - 0.47 nM [3H]ketanserin; inhibition constant low affinity site (Ki (low)); Ki (low) related to: mouse serotonin 2A receptor

Type (Pharmacological Data)

Ki (low)

Value of Type (Pharmacological Data)

92.8 nmol/l

Reference

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

C57BL/6 mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. dissolved in sterile saline; title comp. administered once daily

Further Details (Pharmacological Data)

mass of species: 20 - 30 g

Results

molecular target: mouse serotonin 2A receptor

Reference

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

C57BL/6 mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. dissolved in sterile saline; title comp. administered once daily

Further Details (Pharmacological Data)

mass of species: 20 - 30 g; Bmax related to: serotonin 2A receptor, cortex

Type

Bmax

(Pharmacological Data)

48 of 174

49 of 174

50 of 174

Value of Type (Pharmacological Data)

58.1 fmol/mg protein

Reference

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor binding affinity

Species or TestSystem (Pharmacological Data)

C57BL/6 mouse

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. dissolved in sterile saline; title comp. administered once daily

Further Details (Pharmacological Data)

mass of species: 20 - 30 g; dissociation constant (Kd); Kd related to: serotonin 2A receptor, cortex

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.74 nmol/l

Reference

Dougherty, John P.; Aloyo, Vincent J.

Psychopharmacology, 2011 , vol. 215, # 3 p. 581 - 593 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free radical trapping

Species or TestSystem (Pharmacological Data)

peroxyl radical

Concentration (Pharmacological Data)

0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

total peroxyl radical-trapping antioxidant parameter (TRAP) analysis

Type (Pharmacological Data)

TRAP

Value of Type (Pharmacological Data)

20.3 nmol/ml

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free radical trapping

Species or TestSystem (Pharmacological

peroxyl radical

Data)

51 of 174

52 of 174

Concentration (Pharmacological Data)

0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

total peroxyl radical-trapping antioxidant parameter (TRAP) analysis

Results

molecular target: peroxyl radical

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: CaI; CaI: calcium ionophore; control relative oxidative burst: 39-83 percent; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

0.0001 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: CaI; CaI: calcium ionophore; control relative oxidative burst: 39-83 percent

Type (Pharmacological Data)

relative oxidative burst

Value of Type (Pharmacological Data)

5 percent

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523

Title/Abstract Full Text View citing articles Show Details

53 of 174

54 of 174

55 of 174

Effect (Pharmacological Data)

cell viability; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of human

Concentration (Pharmacological Data)

0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

ATP test

Type (Pharmacological Data)

viability rate

Value of Type (Pharmacological Data)

96 percent

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of human

Concentration (Pharmacological Data)

1E-07 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: CaI; CaI: calcium ionophore; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

1E-5 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of human

Concentration (Pharmacological Data)

1E-07 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological

oxidative burst activator: fMLP; fMLP: N-formyl-methionyl-leucyl-phenylalanine; lowest observed effect concentration (LOEC)

Data)

56 of 174

57 of 174

58 of 174

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

1E-5 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of human

Concentration (Pharmacological Data)

1E-07 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: PMA; PMA: phorbol-12-myristate-13-acetate; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

0.0001 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of human

Concentration (Pharmacological Data)

1E-07 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: opsonized zymosan particles; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

0.0001 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological

polymorphonuclear leukocytes of human

Data)

59 of 174

60 of 174

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: opsonized zymosan particles; inhibition rate: <= 28percent

Results

no effect; insignificant effect(s) discussed

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: fMLP: N-formyl-methionyl-leucyl-phenylalanine; control relative oxidative burst at conc. 1E-6 mol/l: 93 percent; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

1E-5 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: fMLP: N-formyl-methionyl-leucyl-phenylalanine; control relative oxidative burst at conc. 1E-6 mol/l: 93 percent

Type (Pharmacological Data)

relative oxidative burst

Value of Type (Pharmacological Data)

0 - 30 percent

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523

Title/Abstract Full Text View citing articles Show Details

61 of 174

62 of 174

63 of 174

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: PMA; PMA: phorbol-12-myristate-13-acetate; control relative oxidative burst at conc. 1E-6 - 1E-5 mol/l: 86-107 percent; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

0.0001 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: PMA; PMA: phorbol-12-myristate-13-acetate; control relative oxidative burst at conc. 1E-6 - 1E-5 mol/l: 86-107 percent

Type (Pharmacological Data)

relative oxidative burst

Value of Type (Pharmacological Data)

0 percent

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

64 of 174

65 of 174

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: opsonized zymosan particles; control relative oxidative burst at conc. 1E-6 mol/l: 84 percent; lowest observed effect concentration (LOEC)

Type (Pharmacological Data)

LOEC

Value of Type (Pharmacological Data)

1E-5 mol/l

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative burst; inhibition of

Species or TestSystem (Pharmacological Data)

leukocytes of Wistar rat

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

title comp. administered as hydrochloride salt

Further Details (Pharmacological Data)

oxidative burst activator: opsonized zymosan particles; control relative oxidative burst at conc. 1E-6 mol/l: 84 percent

Type (Pharmacological Data)

relative oxidative burst

Value of Type (Pharmacological Data)

0 - 19 percent

Reference

Pracharova, Lucie; Okenkova, Katerina; Lojek, Antonin; Ciz, Milan

Life Sciences, 2010 , vol. 86, # 13-14 p. 518 - 523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

5HT2C receptor; agonist to

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary (CHO) cells transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2C) receptor

Method (Pharmacological Data)

Assessment of Effectiveness of Compounds as 5HT 2c Agonists and Partial Agonists [00165] The ability of the compounds of this invention to act as 5HT2C agonists and partial agonists was established using several standard pharmacological test procedures; the procedures used and results obtained are provided below. In the test procedures, 5-HT stands for 5-hydroxytryptamine, mCPP stands for metachlorophenylpiperazine, and DOI stands for l-(2,5-dimethoxy-4-iodophenyl)isopropylamine.[00166] To evaluate the affinity of various compounds of formula I for activity at the 5- HT2C receptor, a CHO (Chinese Hamster Ovary) cell line transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2c) receptor was maintained in DMEM (Dulbecco's Modified Eagle Media) supplied with fetal calf serum, glutamine, and the markers: guaninephosphoribosyl transferase (GTP) and hypoxanthinethymidine (HT). The cells were allowed to grow to confluence in large culture dishes with intermediate EPO changes of media and splitting. Upon reaching confluence, the cells were harvested by scraping. The harvested cells were suspended in half volume of fresh physiological phosphate buffered saline (PBS) solution and centrifuged at low speed (900 x g). This operation was repeated once. The collected cells were then homogenized with a polytron at setting No.7 for 15 sec in ten volumes of 50 mM Tris.HCl, pH 7.4 and 0.5 mM EDTA. The homogenate was centrifuged at 900 x g for 15 min to remove nuclear particles and other cell debris. The pellet was discarded and the supernatant fluid recentrifuged at 40,000 x g for 30 min. The resulting pellet was resuspended in a small volume of Tris.HCl buffer and the tissue protein content was determined in aliquots of 10-25 μL volumes. Bovine Serum Albumin (BSA) was used as the standard in the protein determination by the method of Lowry et al, (J. Biol. Chem., 193:265 (1951). The volume of the suspended cell membranes was adjusted with 50 mM Tris.HCl buffer containing: 0.1percent ascorbic acid, 10 mM pargyline and 4 mM CaCl2 to give a tissue protein concentration of 1-2 mg per ml of suspension. The preparation membrane suspension (many times concentrated) was aliquoted in 1 ml volumes and stored at -70 C until used in subsequent binding experiments.[00167] Binding measurements were performed in a 96 well microtiter plate format, in a total volume of 200 μL. To each well was added: 60 μL of incubation buffer made in 50 mM Tris.HCl buffer, pH 7.4 and containing 4 mM CaCl2; 20 μL of [125I] DOI

(S.A., 2200 Ci/mmol, NEN Life Science).[00168] The dissociation constant, KD of [125I] DOI at the human serotonin 5-HT2c receptor was 0.4 nM by saturation binding with increasing concentrations of [125I] DOI. The reaction was initiated by the final addition of 100 μL of tissue

suspension containing 50 μg of receptor protein. Nonspecific binding is measured in the presence of 1 μM unlabeled DOI added in 20.0 μL volume. Test compounds were added in 20.0 μL. The mixture was incubated at room temperature for 60 min. The incubation was stopped by rapid filtration. The bound ligand-receptor complex was filtered off on a 96 well unifilter with a Packard .(R).Filtermate 196 Harvester. The bound complex caught on the filter disk was dried in a vacuum oven heated to 60° C and the radioactivity measured by liquid scintillation with 40 μL Microscint-20 scintillant in a Packard TopCount.(R). equipped with six (6) photomultiplier detectors.[00169] Specific binding is defined as the total radioactivity bound less the amount bound in the presence of 1 μM unlabeled DOI. Binding in the presence of varying concentrations of EPO test drugs is expressed as percent of specific binding in the absence of drug. These results are then plotted as logpercent bound vs log concen Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6.2 nmol/l

Location

Page/Page column 128-130

Reference

WYETH

Patent: WO2008/52075 A2, 2008 ; Title/Abstract Full Text Show Details

66 of 174

Effect (Pharmacological Data)

brain 5-HT2C receptor; agonist to

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary (CHO) cells stably expressing the human 5-HT2C receptor

Method (Pharmacological Data)

The ability of the compounds of formula I to produce an agonist response at brain 5 -HT2C was assessed by determining their effect on calcium mobilization using the following procedure: CHO cells stably expressing the human 5-HT2c receptor were cultured in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10percent fetal bovine serum and non-essential amino acids. Cells were plated at a density of 4OK cells/well in 96-well clear-bottom black-wall plates 24 hours prior to the evaluation of 5-HT2c receptor- stimulated calcium mobilization. For calcium studies, cells were loaded with the calcium indicator dye EPO Fluo-3-AM in Hank's buffered saline (HBS) for 60 minutes at 37 0C. Cells were washed with HBS at room temperature and transferred to the fluorometric imaging plate reader (FLIPR, Molecular Devices, Sunnyvale, CA) for acquisition of calcium images. Excitation at 488 nm was achieved with an Argon ion laser and a 510560 nm emission filter was used. Fluorescence images and relative intensities were captured at 1 second intervals and cells were stimulated by addition of agonist after 10 baseline measurements using the internal fluidics module of the FLIPR. An increase in fluorescence counts corresponds to an increase in intracellular calcium.[00172] For the evaluation of agonist pharmacology the calcium changes in response to different concentrations of agonist were determined using a maximum minus minimum calculation of the raw fluorescence count data. Calcium changes were then expressed as a percentage of the response observed with a maximally effective concentration of 5-HT. EC50 values were estimated by non-linear regression analysis of the log-concentrationpercent maximum 5-HT response curves using the 4parameter logistic function. In certain embodiments, compounds of the present invention provide an EC50 of 50 of < about 100 nM, in yet other embodiments < about 20 nM, in still other embodiments < about 5 nM, and certain embodiments < about 2 nM.[00173] The following ECso's are provided for various reference compounds in Table 3, below.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.5 nmol/l

Location

Page/Page column 130-131

Reference

WYETH

Patent: WO2008/52075 A2, 2008 ; Title/Abstract Full Text Show Details

67 of 174

Effect (Pharmacological Data)

5-hydroxytryptamine-2C (h5-HT2C) receptor; binding affinity to

Species or TestSystem (Pharmacological Data)

chinese hamster ovary (CHO) cells expressing 5-hydroxytryptamine-2C (h5-HT2C) receptors of human

Method (Pharmacological Data)

To evaluate the affinity of various compounds of formula I for activity at the 5- HT2C receptor, a CHO (Chinese Hamster Ovary) cell line transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2c) receptor was maintained in DMEM (Dulbecco's Modified Eagle Media) supplied with fetal calf serum, glutamine, and the markers: guaninephosphoribosyl transferase (GTP) and hypoxanthinethymidine (HT). The cells were allowed to grow to confluence in large culture dishes with intermediate changes of media and splitting. Upon reaching confluence, the cells were harvested by scraping. The harvested cells were suspended in half volume of fresh physiological phosphate buffered saline (PBS) solution and centrifuged at low speed (900 x g). This operation was repeated once. The collected cells were then homogenized with a polytron at setting No.7 for 15 sec in ten volumes of 50 mM Tris.HCl, pH 7.4 and 0.5 mM EDTA. The homogenate was centrifuged at 900 x g for 15 min to remove nuclear particles and other cell debris. The pellet was discarded and the supernatant fluid recentrifuged at 40,000 x g for 30 min. The resulting pellet was resuspended in a small volume of Tris.HCl buffer and the tissue protein content was determined in aliquots of 10-25 mL volumes. Bovine Serum Albumin (BSA) was used as the standard in the protein determination by the method of Lowry et al, (J. Biol. Chem., 193:265 (1951). The volume of the suspended cell membranes was adjusted with 50 mM Tris.HCl buffer containing: 0.1percent ascorbic acid, 10 mM pargyline and 4 mM CaCl2 to give a tissue protein

concentration of 1-2 mg per mL of suspension. The preparation membrane suspension (many times concentrated) was aliquoted in 1 mL volumes and stored at -70 0C until used in subsequent binding experiments.[00157] Binding measurements were performed in a 96 well microtiter plate format, in a total volume of 200 μL. To each well was added: 60 μL of incubation buffer made in 50 mM Tris.HCl buffer, pH 7.4 and containing 4 mM CaCl2; 20 μL of [125I] DOI (S.A., 2200 Ci/mmol, NEN Life Science). EPO [00158] The dissociation constant, KD of [125I] DOI at the human serotonin 5-HT2C receptor was 0.4 nM by saturation binding with increasing concentrations of [125I] DOI. The

reaction was initiated by the final addition of 100 μL of tissue suspension containing 50 μg of receptor protein. Nonspecific binding is measured in the presence of 1 μM unlabeled DOI added in 20.0 μL volume. Test compounds were added in 20.0 μL. The mixture was incubated at room temperature for 60 min. The incubation was stopped by rapid filtration. The bound ligand-receptor complex was filtered off on a 96 well unifilter with a Packard .(R).Filtermate 196 Harvester. The bound complex caught on the filter disk was dried in a vacuum oven heated to 60° C and the radioactivity measured by liquid scintillation with 40 μL Microscint-20 scintillant in a Packard TopCount.(R). equipped with six (6) photomultiplier detectors.[00159] Specific binding is defined as the total radioactivity bound less the amount bound in the presence of 1 μM unlabeled DOI. Binding in the presence of varying concentrations of test drugs is expressed as percent of specific binding in the absence of drug. These results are then plotted as logpercent bound vs log concentration of test drug. Non linear regression analysis of data points yields both the IC50 and the K1 values of test compounds with 95percent confidence limits. Alternatively, a linear regression line of decline of data points is plotted, from which the IC50 value can be read off the curve and the K1 value determined by solving the following equation:IC50K1 = -1+L/KD where L is the concentration of the radioactive ligand used and the KD is the dissociation const Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6.2 nmol/l

Location

Page/Page column 68-70

Reference

WYETH

Patent: WO2008/52078 A2, 2008 ; Title/Abstract Full Text Show Details

68 of 174

Effect (Pharmacological Data)

5-hydroxytryptamine-2C (h5-HT2C) receptor; agonist of

Species or TestSystem (Pharmacological Data)

chinese hamster ovary (CHO) cells expressing 5-hydroxytryptamine-2C (h5-HT2C) receptors of human

Method (Pharmacological Data)

The ability of the compounds of formula I to produce an agonist response at brain 5-HT2C was assessed by determining their effect on calcium mobilization using the following procedure: CHO cells stably expressing the human 5-HT2c receptor were cultured in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10percent fetal bovine serum and non-essential amino acids. Cells were plated at a density of 4OK cells/well in 96-well clear-bottom black-wall plates 24 hours prior to the evaluation of 5-HT2c receptor- stimulated calcium mobilization. For calcium studies, cells were loaded with the calcium indicator dye Fluo-3-AM in Hank's buffered saline (HBS) for 60 minutes at 37 0C. Cells were washed with HBS at room temperature and transferred to the fluorometric imaging plate reader (FLIPR, Molecular Devices, Sunnyvale, CA) for acquisition of calcium images. Excitation at 488 nm was achieved with an Argon ion laser and a 510-560 nm emission filter was used. Fluorescence images and relative intensities were captured at 1 second intervals and cells were stimulated by addition of agonist after 10 baseline measurements using the internal fluidics module of the FLIPR. An increase in fluorescence counts corresponds to an increase in intracellular calcium.[00162] For the evaluation of agonist pharmacology the calcium changes in response to different concentrations of agonist were determined using a maximum minus minimum calculation of the raw fluorescence count data. Calcium changes were then expressed as a percentage of the response observed with a maximally effective concentration of 5-HT. EC50 values were estimated by non-linear regression analysis of the log-concentrationpercent maximum 5-HT response curves using the 4parameter logistic function. In certain embodiments, compounds of the present invention provide an EC50 of [00163] The following ECso's are provided for various reference compounds in Table 3, belowTable 3: ECsn Data for Reference Compounds:Compound EC505-HT EC50 5 nMDOI EC50 0.5 nM mCPP EC50 5.4 nMSB242084 0.01 nMSB206553 13 nMTable 4. 5-HT2c Activity of Selected Compounds[00164] The compounds of this invention thus have affinity for and agonist or partial agonist activity at brain serotonin 5HT2c receptors. They are therefore of interest for the treatment of the central nervous system conditions described previously herein.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.5 nmol/l

Location

Page/Page column 70-71

Reference

WYETH

Patent: WO2008/52078 A2, 2008 ; Title/Abstract Full Text Show Details

69 of 174

Effect (Pharmacological Data)

5-hydroxytryptamine-2C (h5-HT2C) receptor; binding affinity to

Species or TestSystem (Pharmacological

chinese hamster ovary (CHO) cells expressing 5-hydroxytryptamine-2C (h5-HT2C) receptor of human

Data) Method (Pharmacological Data)

To evaluate the affinity of various compounds of formula I for activity at the 5-HT2c receptor, a CHO (Chinese Hamster Ovary) cell line transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2c) receptor is maintained in DMEM (Dulbecco's Modified Eagle Media) supplied with fetal calf serum, glutamine, and the markers: EPO guaninephosphoribosyl transferase (GTP) and hypoxanthinethymidine (HT). The cells are allowed to grow to confluence in large culture dishes with intermediate changes of media and splitting. Upon reaching confluence, the cells are harvested by scraping. The harvested cells are suspended in half volume of fresh physiological phosphate buffered saline (PBS) solution and centrifuged at low speed (900 x g). This operation is repeated once. The collected cells are then homogenized with a polytron at setting No.7 for 15 sec in ten volumes of 50 mM Tris.HCl, pH 7.4 and 0.5 mM EDTA. The homogenate is centrifuged at 900 x g for 15 min to remove nuclear particles and other cell debris. The pellet is discarded and the supernatant fluid recentrifuged at 40,000 x g for 30 min. The resulting pellet is resuspended in a small volume of Tris.HCl buffer and the tissue protein content is determined in aliquots of 10-25 μL volumes. Bovine Serum Albumin (BSA) is used as the standard in the protein determination by the method of Lowry et al, (J. Biol. Chem., 193:265 (1951). The volume of the suspended cell membranes is adjusted with 50 mM Tris.HCl buffer containing: 0.1percent ascorbic acid, 10 mM pargyline and 4 mM CaCl2 to give a tissue protein concentration of 1-2 mg per ml of suspension. The preparation membrane suspension (many times concentrated) is aliquoted in 1 ml volumes and stored at -70 C until used in subsequent binding experiments.[00169] Binding measurements are performed in a 96 well microtiter plate format, in a total volume of 200 μL. To each well is added: 60 μL of incubation buffer made in 50 mM Tris.HCl buffer, pH 7.4 and containing 4 mM CaCl2; 20 μL of [125I] DOI (S.A., 2200 Ci/mmol, NEN Life Science).[00170] The dissociation constant, KD of [125I] DOI at the human serotonin 5 -HT2C receptor is 0.4 nM by saturation binding with increasing concentrations of [125I] DOI. The reaction is initiated by the final

addition of 100 μL of tissue suspension containing 50 μg of receptor protein. Nonspecific binding is measured in the presence of 1 μM unlabeled DOI added in 20.0 μL volume. Test compounds are added in 20.0 μL. The mixture is incubated at room temperature for 60 min. The incubation is stopped by rapid filtration. The bound ligand-receptor complex is filtered off on a 96 well unifilter with a Packard . (R).Filtermate 196 Harvester. The bound complex caught on the filter disk is dried in a vacuum oven heated to 60° C and the radioactivity measured by liquid scintillation with 40 μL Microscint-20 scintillant in a Packard TopCount.(R). equipped with six (6) photomultiplier detectors. EPO [00171] Specific binding is defined as the total radioactivity bound less the amount bound in the presence of 1 μM unlabeled DOI. Binding in the presence of varying concentrations of test drugs is expressed as percent of specific binding in the absence of drug. These results are then plotted as logpercent bound vs log concentration of test drug. Non linear regression analysis of data points yields both the EC50 and the K1 values of test compounds with 95percent confidence limits. Alternatively, a linear regression line of decline of data points is plotted, from which the EC50 value can be read off the curve and the K1 value determined by solving the following equation:IC50Ki =1+L/KD where L is the concentration of the radioactive ligand used and the KD is the dissociation constant of the ligan Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6.2 nmol/l

Location

Page/Page column 49-51

Reference

WYETH

Patent: WO2008/52086 A1, 2008 ; Title/Abstract Full Text Show Details

70 of 174

Effect (Pharmacological Data)

5-hydroxytryptamine-2C (h5-HT2C) receptor; agonist of

Species or TestSystem (Pharmacological Data)

chinese hamster ovary (CHO) cells expressing 5-hydroxytryptamine-2C (h5-HT2C) receptor of human

Method (Pharmacological Data)

The ability of the compounds of formula I to produce an agonist response at brain 5- HT2C is assessed by determining their effect on calcium mobilization using the following procedure: CHO cells stably expressing the human 5-HT2c receptor are cultured in Dulbecco's modified Eagle's medium (DMEM) supplemented with 10percent fetal bovine serum and nonessential amino acids. Cells are plated at a density of 4OK cells/well in 96-well clear-bottom EPO black- wall plates 24 hours prior to the evaluation of 5-HT2C receptor- stimulated calcium mobilization. For calcium studies, cells are loaded with the calcium indicator dye Fluo-3-AM in Hank's buffered saline (HBS) for 60 minutes at 37 0C. Cells are washed with HBS at room temperature and transferred to the fluorometric imaging plate reader (FLIPR, Molecular Devices, Sunnyvale, CA) for acquisition of calcium images. Excitation at 488 nm is achieved with an Argon ion laser and a 510560 nm emission filter is used. Fluorescence images and relative intensities are captured at 1 second intervals and cells were stimulated by addition of agonist after 10 baseline measurements using the internal fluidics module of the FLIPR. An increase in fluorescence counts corresponds to an increase in intracellular calcium.[00174] For the evaluation of agonist pharmacology the calcium changes in response to different concentrations of agonist are determined using a maximum minus minimum calculation of the raw fluorescence count data. Calcium changes are then expressed as a percentage of the response observed with a maximally effective concentration of 5-HT. EC50 values are estimated by non-linear regression analysis of the log-concentrationpercent maximum 5-HT response curves using the 4parameter logistic function. In certain embodiments, compounds of the present invention provide an EC50 of < about 1000 nM. In other embodiments, compounds of the present invention provide an EC50 of < about 100 nM, in yet other embodiments < about 20 nM, in still other embodiments < about 5 nM, and certain embodiments < about 2 nM. [00175] The following ECso's are provided for various reference compounds in Table 3, belowTable 3: EC^n Data for Reference Compounds:Compound EC505-HT 0.5 nMDOI 0.5 nM mCPP 5.4 nM

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.5 nmol/l

Location

Page/Page column 49-51

Reference

WYETH

Patent: WO2008/52086 A1, 2008 ; Title/Abstract Full Text Show Details

71 of 174

72 of 174

73 of 174

74 of 174

Effect (Pharmacological Data)

functional activity

Species or TestSystem (Pharmacological Data)

rat

Method (Pharmacological Data)

drug discrimination assay using rats trained to distinguish the 5-HT2A receptor agonist LSD from saline; rat behavior observed

Results

title comp. indirectly determined to be an agonist of 5-HT2A receptor

Reference

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 8 p. 4661 - 4669 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

A549 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (A20) incubated with title comp. and <3H>ketanserin as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

29 nmol/l

Reference

Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

A549 cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (A20) incubated with title comp. and <3H>INBMeO as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Further Details (Pharmacological Data)

<3H>INBmeO: N-(2-<3H>methoxybenzyl)-2-(2-<3H>methoxy-5-methoxy-4-iodophenyl)ethylamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

28 nmol/l

Reference

Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

HEK cells expressing human 5-HT2A receptor

75 of 174

76 of 174

77 of 174

Method (Pharmacological Data)

competition binding assay; test cells (Hh2A) incubated with title comp. and <3H>ketanserin as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

13 nmol/l

Reference

Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

HEK cells expressing human 5-HT2A receptor

Method (Pharmacological Data)

competition binding assay; test cells (Hh2A) incubated with title comp. and <3H>INBMeO as radioligand at 25 deg C for 60 min; scintillation fluid added and radioactivity determined using scintillation counter

Further Details (Pharmacological Data)

<3H>INBmeO: N-(2-<3H>methoxybenzyl)-2-(2-<3H>methoxy-5-methoxy-4-iodophenyl)ethylamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

14 nmol/l

Reference

Nichols, David E.; Frescas, Stewart P.; Chemel, Benjamin R.; Rehder, Kenneth S.; Zhong, Desong; Lewin, Anita H.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6116 - 6123 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or TestSystem (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor

Further Details (Pharmacological Data)

Ki related to: 5-HT2A receptor

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.92 nmol/l

Location

supporting information

Reference

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.

Journal of Medicinal Chemistry, 2008 , vol. 51, # 21 p. 6808 - 6828 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or TestSystem (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor

Results

molecular target: 5-HT2A receptor

Location

supporting information

Reference

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.

Journal of Medicinal Chemistry, 2008 , vol. 51, # 21 p. 6808 - 6828

Title/Abstract Full Text View citing articles Show Details

78 of 174

79 of 174

80 of 174

81 of 174

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or TestSystem (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor, F340L mutant

Results

molecular target: 5-HT2A receptor mutant

Reference

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.

Journal of Medicinal Chemistry, 2008 , vol. 51, # 21 p. 6808 - 6828 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

[3H]ketanserin binding; inhibition of

Species or TestSystem (Pharmacological Data)

NIH3T3 cell; genetically modified/infected with: 5-HT2A receptor, F340L mutant

Further Details (Pharmacological Data)

Ki related to: 5-HT2A receptor mutant

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

13700 nmol/l

Reference

Runyon, Scott P.; Mosier, Philip D.; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.

Journal of Medicinal Chemistry, 2008 , vol. 51, # 21 p. 6808 - 6828 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2C receptors

Method (Pharmacological Data)

cells in serum-free medium labeled with 1 μCi/ml myo-<3H>inositol 24 h and with 0.1 μCi/ml <3H>AA 4 h at 37 deg C; then treated 10 min with title comp.; dose-response curve for total IP accumulation and AA release calculated

Further Details (Pharmacological Data)

control: vehicle; AA: arachidonic acid; IP: inositol phosphate; CHO: Chinese hamster ovary; data expressed as percent of maximal response to 5-HT; 5-HT: serotonin; PLA2 and PLC: phospholipase A2 and phospholipase C, resp.; RE: relative efficacy

Results

title comp. preferentially stimulated PLA2-mediated AA release (RE = ca. 100percent, pEC50 = 6.8); RE for PLC-mediated IP response was ca. 60percent, pEC50 = 6.72 (figures, table)

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

8.4 μmol/kg

Method

immediately after title comp. injection rats placed in dark Plexiglas box and number of head shakes was quantified for 25 min, starting 5

82 of 174

83 of 174

84 of 174

(Pharmacological Data)

min after title comp. administration

Further Details (Pharmacological Data)

control: saline; further investigation with ketanserin, 5-HT2 receptor antagonist; 5-HT: serotonin

Results

title comp. induced robust head shake behavior in comparison with control; pretreatment with 5-HT2 antagonist ketanserin abolished effect of title comp. (figure)

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2A receptors

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Results

title comp. preferentially stimulated PLA2-mediated AA release (RE = ca. 65percent, pEC50 = 6.85); RE for PLC-mediated IP response was ca. 35percent, pEC50 = 6.53 (figures, table)

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

GIRK channel stimulation; inhibition of

Species or TestSystem (Pharmacological Data)

arcuate proopiomelanocortin neurons of Topeka guinea pig

Sex

male and female

Concentration (Pharmacological Data)

Ca. 0.1 - 200 μmol/l

Kind of Dosing (Pharmacological Data)

dissolved in H2O

Method (Pharmacological Data)

guinea pigs gonadectomized 6-10 days before study; standard whole-cell recording made at 35 deg C, responses to 5 μM baclofen measured after 15-min title comp. treatment, in voltage clamp as outward current (holding potential: -60 mV)

Further Details (Pharmacological Data)

baclofen activates G protein-coupled inwardly rectifying potassium (GIRK) channels; further studies in presence of 17β-estradiol

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

16.5 μmol/l

Results

title comp. dose-dependently inhibited baclofen responses (at 20 μM by 30percent); additive effect with 17β-estradiol; fig.

Reference

Qiu, Jian; Xue, Changhui; Bosch, Martha A.; Murphy, Jonathan G.; Fan, Wei; Ronnekleiv, Oline K.; Kelly, Martin J.

Molecular Pharmacology, 2007 , vol. 72, # 4 p. 885 - 896 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anorectic

Species or TestSystem

C57BL/6J mouse

(Pharmacological Data)

85 of 174

Sex

female

Route of Application

intracerebroventricular

Concentration (Pharmacological Data)

10 - 110 nmol

Kind of Dosing (Pharmacological Data)

dissolved in H2O; in volume of 2 μl, infused over 1 min

Method (Pharmacological Data)

mice ovariectomized, title comp. given after overnight fast; body weight and pellet weights det. for up to 24 h postdosing

Further Details (Pharmacological Data)

control: saline

Results

20 nM title comp. inhibited food intake at 6 h, 110 nM strongly inhibited food intake and body weight gain starting at 1 h, with maximal effect at 6 h; fig.

Reference

Qiu, Jian; Xue, Changhui; Bosch, Martha A.; Murphy, Jonathan G.; Fan, Wei; Ronnekleiv, Oline K.; Kelly, Martin J.

Molecular Pharmacology, 2007 , vol. 72, # 4 p. 885 - 896 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

locomotor behaviors; effect on

Species or TestSystem (Pharmacological Data)

DAT-KO mouse

Sex

male and female

Route of Application

intraperitoneal

Method (Pharmacological Data)

Experimental We report here that the pharmacologic inhibition of the rate-limiting enzyme of DA synthesis, TH, almost immediately depletes brain DA to undetectable levels in DAT-KO mice and induces a transient recapitulation of essentially all PD symptoms for up to 16 h. DA-deficient DAT-KO mice (DDD mice) thus represent an acute PD model that is useful for studying the efficacy of compounds that potentially can restore control of locomotion in the absence of any contribution of the dopaminergic system. By using this approach, we found that several amphetamine derivatives can counteract the behavioral manifestations of severe DA deficiency, suggesting that, in addition to well-known DA-mediated effects, amphetamine-like compounds can also affect motor functions in a DA- and DAT-independent manner. Materials and Methods Animals. DAT-KO mice were generated as previously described [11]. Animal care was in accordance with the Guide for Care and Use of Laboratory Animals (National Institutes of Health publication No.865-23, Bethesda, Md., United States) with an approved protocol from the Duke University Institutional Animal Care and Use Committee. C57BL/6J3129Sv/J hybrid WT and DAT-KO mice, 3-5 mo old, of both sexes were used. None of animals used in these studies had the neurodegenerative phenotype sporadically observed in DAT-KO mice [60]. Drugs. Drugs or saline (0.9percent NaCl) were administered intraperitoneally (IP) or subcutaneously (SC) in a volume of 10 ml/kg. The drags were either from Sigma (St. Louis, Mo., United States) or supplied by the National Institute of Drug Abuse (NIDA). Drugs provided by the NIDA Drug Supply Program included: (+/-)-MDMA, (+)-MDMA, (+/-)-6-OH-MDA, (+/-)-MDA, (+/-)-MDE, (+)-MDE, (-)-MDE, and AFT (alpha-ethyl-tryptamine acetate). Neurochemical assessments. Striatal tissue contents of DA and frontal cortical tissue levels of NE were assessed using HPLC-EC (high performance liquid chromatography with electrochemical detection) as described [8]. In vivo microdialysis measurements of striatal extracellular DA levels in freely moving mice were performed at least 24 h after implantation of a microdialysis probe as described previously [50]. Dialysate samples were assayed for DA using HPLC-EC. Behavioral methods. Locomotor activity of littermate WT and DATKO mice was measured in an Omnitech CCDigiscan (Accuscan Instruments, Columbus, Ohio United States) activity monitor under bright illumination [83]. All behavioral experiments were performed between 10:00 AM and 5:00 PM. Activity was measured at 5-min intervals, To evaluate the effects of drugs on motor behaviors, mice were placed into activity monitor chambers (20.x.20 cm) for 30 min and then treated with αMT (250 mg/kg IP). A drug or combination of drugs were injected 1 h after αMT administration, and various parameters of locomotor activity were monitored for up to 3 h. In cumulative dosing experiments, animals were treated with increasing doses of drugs after a 1-h interval. For the akinesia test, the mouse is held by the tail so that it is standing on forelimbs only and moving on its own. The number of steps taken with both forelimbs was recorded during a 30-s trial [57]. The presence of catalepsy was determined and measured by placing the animal's forepaws on a horizontal wooden bar (0.7 cm in diameter), 4 cm above the tabletop. The time until the mouse removed both forepaws from the bar was recorded, with a maximum cut-off time of 3 min [53]. In the grasping test of muscular rigidity, the mouse is suspended by its forelimbs on a metal rod (diameter: 0.25 cm) positioned approximately 20 cm above the table. The time the animal remains on the rod (maximum 1 min) was noted [58]. To assess rigidity in a bracing task, the number of steps taken with each forelimb when the mouse is pushed sideways over a distance of 50 cm was recorded [57]. Tremor was scored visually in mice using the rating scale [54]: 0, no tremor; 1, occasional isolated twi

Results

Akinesia test: 0-20 number of steps; at Catalepsy test: 180sec; at Grasping test: 10-29 seconds time spent on the rod of the title compound administered after 1h of αMT treatment; figure is given

Location

Page/Page column 12-17

Reference

Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.

Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details

86 of 174

Effect (Pharmacological

leak point pressure; effect on

Data) Species or TestSystem (Pharmacological Data)

SD rat

Sex

female

Route of Application

intravenous

Method (Pharmacological Data)

Example 3 [Experimental method] SD female rats (body weight 180-350 g) were anesthetized with urethane (Wako Pure Chemical Industries, Ltd.), and the spinal cord was transected at T8-9 level to eliminate the reflex voiding. In addition, the nerve to the iliococcygeus muscle/pubococcygeus muscle on the one side was transected. During operation, halothane (Takeda Pharmaceutical Company Limited) anesthesia was added when necessary. A catheter (PE-90, Clay Adams) was inserted into the bladder and secured with a ligature, and the incised part of each of the abdominal muscle and skin was closed with sutures. The abdominal skin near the diaphragm was incised at two left and right positions to newly expose the abdominal muscle. An Evans Blue dye (Merck) solution was injected into the bladder, and the bladder volume was adjusted to 0.2 - 0.3 ml. The bladder catheter was connected to a pressure transducer, and the signals of the transducer were sent to a computer via an amplifier (blood pressure amplification unit AP-641G; NIHON KOHDEN) and an analog-to-digital converter (BIOPAC; MP100), and recorded on a hard disc. The data were analyzed on a computer using software (BIOPAC; AcqKnowledge). The exposed abdominal muscle was electrostimulated using an electrostimulator (SEN-3301; NIHON KODEN) and an isolator (SS-202J; NIHON KODEN), and the presence or absence of incontinence from the meatus urethra was observed. The electrostimulation was applied at a voltage of 2.5 - 50 V, duration of 0.5 milisec, and frequency 50 Hz for 1 sec, thereby gradually increasing the intravesical pressure. The peak intravesical pressure during stimulation of the abdominal wall was measured and, of the trials with observed incontinence, the lowest peak intravesical pressure was defined as the leak point pressure. Serotonin 5-HT receptor agonist, WAY-161503 (5-HT2C receptor agonist), WAY-163909 (5-HT2C receptor agonist), DOI (5-HT2A/2B/2C receptor agonist), mCPP (5-HT2B/2C receptor partial agonist), eltoprazine (5-HT1A/1B/2C receptor partial agonist), 8-OH-DPAT (5-HT1A receptor agonist), sumatryptan (5-HT1B/1D receptor agonist) and BW723C86 (5-HT2B receptor agonist) were intravenously administered, and the leak point pressure was compared before and after the administration. DOI, mCPP and eltoprazine were dissolved in saline, and other drugs were dissolved in DMA/PEG400 (1:1), and they were intravenously administered at 1 ml/kg and 0.5 mg/kg, respectively. Depending on the experiment, RS-102221 (serotonin 5-HT2C receptor antagonist) or SB221284 (serotonin 5-HT2B/2C receptor antagonist) was intravenously administered 5 min before WAY-161503 or WAY163909 administration, and an antagonistic effect against the WAY-161503 or WAY-163909-induced increment of the leak point pressure was examined. RS-102221 and SB221284 were both dissolved in DMA/PEG400 (1:1) and intravenously administered at 0.5 ml/kg.[Results] Intravenous administration of WAY-161503 and WAY-163909, which are serotonin 5-HT2C receptor agonists, dose-dependently increased the leak point pressure, and a significant effect was afforded at a dose of not less than 0.03 mg/kg and not less than 0.1 mg/kg, respectively (Table 3). However, WAY-163907 (The Journal of Pharmacology and Experimental Therapeutics, 313, 862-869, 2005), which is an optical isomer of WAY-163909 and which is considered to be free of 5-HT2C receptor agonist activity, showed no effect (Table 3). DOI (5-HT2A/2B/2C receptor agonist), mCPP (5-HT2B/2C receptor partial agonist) and eltoprazine (5-HT1A/1B/2C receptor partial agonist), which have a serotonin 5-HT2C receptor agonist activity, respectively increased the leak point pressure significantly (Table 3). However, 8OH-DPAT, sumatryptan and BW723C86, which are 5-HT1A receptor agonist, 5-HT1B/1D</SU

Results

title compound at 0.01-1mgkg showed that before drug administration leak point pressure is 36.4-67.0cmH2O while 39.7-85.7cmH2O was observed after drug administration

Location

Page/Page column 27-31

Reference

Takeda Pharmaceutical Company Limited

Patent: EP1792629 A1, 2007 ; Title/Abstract Full Text Show Details

87 of 174

Effect (Pharmacological Data)

serotonin 5-HT2C receptor; binding affinity

Species or TestSystem (Pharmacological Data)

serotonin 5-HT2C receptor of human

Method (Pharmacological Data)

A. Assessment of Effectiveness of Compounds as 5HT2C Agonists and Partial Agonists[00187] The ability of the compounds of this invention to act as 5HT2c agonists and partial agonists was established using several standard pharmacological test procedures; the procedures used and results obtained are provided below. In the test procedures, 5-HT stands for 5-hydroxytryptamine, mCPP stands for meta-chlorophenylpiperazine, and DOI stands for l-(2,5-dimethoxy-4-iodophenyl)isopropylamine.[00188] To evaluate the affinity of various compounds of formula I for activity at the 5- HT2C receptor, a CHO (Chinese Hamster Ovary) cell line transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2c) receptor was maintained in DMEM (Dulbecco's Modified Eagle Media) supplied with fetal calf serum, glutamine, and the markers: guaninephosphoribosyl transferase (GTP) and hypoxanthinethymidine (HT). EPO The cells were allowed to grow to confluence in large culture dishes with intermediate changes of media and splitting. Upon reaching confluence, the cells were harvested by scraping. The harvested cells were suspended in half volume of fresh physiological phosphate buffered saline (PBS) solution and centrifuged at low speed (900 x g). This operation was repeated once. The collected cells were then homogenized with a polytron at setting No.7 for 15 sec in ten volumes of 50 mM Tris.HCl, pH 7.4 and 0.5 mM EDTA. The homogenate was centrifuged at 900 x g for 15 min to remove nuclear particles and other cell debris. The pellet was discarded and the supernatant fluid recentrifuged at 40,000 x g for 30 min. The resulting pellet was resuspended in a small volume of Tris.HCl buffer and the tissue protein content was determined in aliquots of 10-25 μL volumes. Bovine Serum Albumin (BSA) was used as the standard in the protein determination by the method of Lowry et al., (J. Biol. Chem., 193:265 (1951). The volume of the suspended cell membranes was adjusted with 50 mM Tris.HCl buffer containing: 0.1percent ascorbic acid, 10 mM pargyline and 4 mM CaCl2 to give a tissue protein concentration of 1-2 mg per ml of suspension. The preparation membrane suspension (many times concentrated) was aliquoted in 1 ml volumes and stored at -70 C until used in subsequent binding experiments.[00189] Binding measurements were performed in a 96 well microtiter plate format, in a total volume of 200 μL. To each well was added: 60 μL of incubation buffer made in 50 mM Tris.HCl buffer, pH 7.4 and containing 4 mM CaCl2; 20 μL of [125I] DOI

(S.A., 2200 Ci/mmol, NEN Life Science).[00190] The dissociation constant, K0 of [125I] DOI at the human serotonin 5-HT2C receptor was 0.4 nM by saturation binding with increasing concentrations of [ I] DOI. The reaction was initiated by the final addition of 100 μL of tissue suspension containing 50 μg of receptor protein. Nonspecific binding is measured in the presence of 1 μM unlabeled DOI added in 20.0 μL volume. Test compounds were added in 20.0 μL. The mixture was incubated at room temperature for 60 min. The incubation was stopped by rapid filtration. The bound ligand-receptor complex was filtered off on a 96 well unifilter with a Packard .(R).Filtermate 196 Harvester.

The bound complex caught on the filter disk was dried in a vacuum oven heated to 60° C and the radioactivity measured by liquid scintillation with 40 μL Microscint-20 scintillant in a Packard TopCount.(R). equipped with six (6) photomultiplier detectors. [00191] Specific binding is defined as the total radioactivity bound less the amount bound in the nresence of 1 uM unlabeled DOI. Binding in the presence of varying concentrations of EPO test drags is expressed as percent of specific binding in the absence of drag. These results are then plotted as logpercent bound vs log concentr Type (Pharmacological Data)

Ki avg

Value of Type (Pharmacological Data)

6.2 nmol/l

Location

Page/Page column 120-124

Reference

WYETH

Patent: WO2006/116165 A1, 2006 ; Title/Abstract Full Text Show Details

88 of 174

Effect (Pharmacological Data)

serotonin 5-HT2C receptor agonist

Species or TestSystem (Pharmacological Data)

serotonin 5-HT2C receptor of human

Method (Pharmacological Data)

0.4 nM by saturation binding with increasing concentrations of [ I] DOI. The reaction was initiated by the final addition of 100 μL of tissue suspension containing 50 μg of receptor protein. Nonspecific binding is measured in the presence of 1 μM unlabeled DOI added in 20.0 μL volume. Test compounds were added in 20.0 μL. The mixture was incubated at room temperature for 60 min. The incubation was stopped by rapid filtration. The bound ligand-receptor complex was filtered off on a 96 well unifilter with a Packard .(R).Filtermate 196 Harvester. The bound complex caught on the filter disk was dried in a vacuum oven heated to 60° C and the radioactivity measured by liquid scintillation with 40 μL Microscint-20 scintillant in a Packard TopCount.(R). equipped with six (6) photomultiplier detectors. [00191] Specific binding is defined as the total radioactivity bound less the amount bound in the nresence of 1 uM unlabeled DOI. Binding in the presence of varying concentrations of EPO test drags is expressed as percent of specific binding in the absence of drag. These results are then plotted as logpercent bound vs log concentr Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.5 nmol/l

Location

Page/Page column 120-124

Reference

WYETH

Patent: WO2006/116165 A1, 2006 ; Title/Abstract Full Text Show Details

89 of 174

Effect (Pharmacological Data)

serotonin 5-HT2c receptor agonist

Species or TestSystem (Pharmacological Data)

5-hydroxytryptamine-2C receptors (5-HT2C) of human

Method

A. Assessment of Effectiveness of Compounds as 5HT

Agonists and Partial Agonists The ability of the compounds of this invention to act

(Pharmacological Data)

as 5HT2C agonists and partial agonists was established using several standard pharmacological test procedures; the procedures used and results obtained are provided below. In the test procedures, 5-HT stands for 5-hydroxytryptamine, mCPP stands for metachlorophenylpiperazine, and DOI stands for 1-(2,5-dimethoxy-4-iodophenyl)isopropylamine. To evaluate the affinity of various compounds of formula I for activity at the 5-HT2C receptor, a CHO (Chinese Hamster Ovary) cell line transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2C) receptor was maintained in DMEM (Dulbecco's Modified Eagle Media) supplied with fetal calf serum, glutamine, and the markers: guaninephosphoribosyl transferase (GTP) and hypoxanthinethymidine (HT). The cells were allowed to grow to confluence in large culture dishes with intermediate changes of media and splitting. Upon reaching confluence, the cells were harvested by scraping. The harvested cells were suspended in half volume of fresh physiological phosphate buffered saline (PBS) solution and centrifuged at low speed (900.x.g). This operation was repeated once. The collected cells were then homogenized with a polytron at setting No.7 for 15 sec in ten volumes of 50 mM Tris.HCl, pH 7.4 and 0.5 mM EDTA. The homogenate was centrifuged at 900.x.g for 15 min to remove nuclear particles and other cell debris. The pellet was discarded and the supernatant fluid recentrifuged at 40,000.x.g for 30 min. The resulting pellet was resuspended in a small volume of Tris.HCl buffer and the tissue protein content was determined in aliquots of 10-25 μL volumes. Bovine Serum Albumin (BSA) was used as the standard in the protein determination by the method of Lowry et al., (J. Biol. Chem., 193:265 (1951). The volume of the suspended cell membranes was adjusted with 50 mM Tris.HCl buffer containing: 0.1percent ascorbic acid, 10 mM pargyline and 4 mM CaCl2 to give a tissue protein concentration of 1-2 mg per mL of suspension. The preparation membrane suspension (many times concentrated) was aliquoted in 1 mL volumes and stored at -70° C. until used in subsequent binding experiments. Binding measurements were performed in a 96 well microtiter plate format, in a total volume of 200 μL. To each well was added: 60 μL of incubation buffer made in 50 mM Tris.HCl buffer, pH 7.4 and containing 4 mM CaCl2; 20 μL of [125I] DOI (S.A., 2200 Ci/mmol, NEN Life Science). The dissociation constant, KD of [125I] DOI at the human serotonin 5-HT2C receptor was 0.4 nM by saturation binding with

increasing concentrations of [125I] DOI. The reaction was initiated by the final addition of 100 μL of tissue suspension containing 50 μg of receptor protein. Nonspecific binding is measured in the presence of 1 μM unlabeled DOI added in 20.0 μL volume. Test compounds were added in 20.0 μL. The mixture was incubated at room temperature for 60 min. The incubation was stopped by rapid filtration. The bound ligand-receptor complex was filtered off on a 96 well unifilter with a Packard.(R). Filtermate 196 Harvester. The bound complex caught on the filter disk was dried in a vacuum oven heated to 60° C. and the radioactivity measured by liquid scintillation with 40 μL Microscint-20 scintillant in a Packard TopCount.(R). equipped with six (6) photomultiplier detectors. Specific binding is defined as the total radioactivity bound less the amount bound in the presence of 1 μM unlabeled DOI. Binding in the presence of varying concentrations of test drugs is expressed as percent of specific binding in the absence of drug. These results are then plotted as log percent bound vs log concentration of test drug. Non linear regression analysis of data points yiel

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.5 nmol/l

Location

Page/Page column 83-85

Reference

Wyeth

Patent: US2006/241172 A1, 2006 ; Title/Abstract Full Text Show Details

90 of 174

Effect (Pharmacological Data) Species or TestSystem (Pharmacological Data) Method (Pharmacological Data)

serotonin 5-HT2c receptor; binding affinity

5-hydroxytryptamine-2C receptors (5-HT2C) of human

A. Assessment of Effectiveness of Compounds as 5HT2C Agonists and Partial Agonists The ability of the compounds of this invention to act as 5HT2C agonists and partial agonists was established using several standard pharmacological test procedures; the procedures used and results obtained are provided below. In the test procedures, 5-HT stands for 5-hydroxytryptamine, mCPP stands for metachlorophenylpiperazine, and DOI stands for 1-(2,5-dimethoxy-4-iodophenyl)isopropylamine. To evaluate the affinity of various compounds of formula I for activity at the 5-HT2C receptor, a CHO (Chinese Hamster Ovary) cell line transfected with the cDNA expressing the human 5-hydroxytryptamine-2C (h5-HT2C) receptor was maintained in DMEM (Dulbecco's Modified Eagle Media) supplied with fetal calf serum, glutamine, and the markers: guaninephosphoribosyl transferase (GTP) and hypoxanthinethymidine (HT). The cells were allowed to grow to confluence in large culture dishes with intermediate changes of media and splitting. Upon reaching confluence, the cells were harvested by scraping. The harvested cells were suspended in half volume of fresh physiological phosphate buffered saline (PBS) solution and centrifuged at low speed (900.x.g). This operation was repeated once. The collected cells were then homogenized with a polytron at setting No.7 for 15 sec in ten volumes of 50 mM Tris.HCl, pH 7.4 and 0.5 mM EDTA. The homogenate was centrifuged at 900.x.g for 15 min to remove nuclear particles and other cell debris. The pellet was discarded and the supernatant fluid recentrifuged at 40,000.x.g for 30 min. The resulting pellet was resuspended in a small volume of Tris.HCl buffer and the tissue protein content was determined in aliquots of 10-25 μL volumes. Bovine Serum Albumin (BSA) was used as the standard in the protein determination by the method of Lowry et al., (J. Biol. Chem., 193:265 (1951). The volume of the suspended cell membranes was adjusted with 50 mM Tris.HCl buffer containing: 0.1percent ascorbic acid, 10 mM pargyline and 4 mM CaCl2 to give a tissue protein concentration of 1-2 mg per mL of suspension. The preparation membrane suspension (many times concentrated) was aliquoted in 1 mL volumes and stored at -70° C. until used in subsequent binding experiments. Binding measurements were performed in a 96 well microtiter plate format, in a total volume of 200 μL. To each well was added: 60 μL of incubation buffer made in 50 mM Tris.HCl buffer, pH 7.4 and containing 4 mM CaCl2; 20 μL of [125I] DOI (S.A., 2200 Ci/mmol, NEN Life Science). The dissociation constant, KD of [125I] DOI at the human serotonin 5-HT2C receptor was 0.4 nM by saturation binding with

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

6.2 nmol/l

Location

Page/Page column 83-85

Reference

Wyeth

Patent: US2006/241172 A1, 2006 ; Title/Abstract Full Text Show Details

91 of 174

92 of 174

93 of 174

Effect (Pharmacological Data)

anxiolytic

Species or TestSystem (Pharmacological Data)

ICR mouse

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1.5 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in 0.9 percent saline

Method (Pharmacological Data)

elevated plus-maze test performed; plus maze consisted of 2 open arms and 2 closed arms elevated 50 cm from floor; mouse placed in centre of maze facing one of open arms; number of entries into each arm and time spent measured for 5 min

Further Details (Pharmacological Data)

elevated plus maze test uses aversion of rodents to heights and open spaces; test performed 60 min after berberine (100 mg/kg, p.o.) and 30 min after title comp. treatment

Results

title comp. alone had anxiolytic effect and it markedly decreased arm entries and time spent in closed arms and increased arm entries and time spent in open arms by berberine

Reference

Peng, Wen-Huang; Wu, Chi-Rei; Chen, Chia-Sheng; Chen, Chung-Fung; Leu, Zong-Chung; Hsieh, Ming-Tsuen

Life Sciences, 2004 , vol. 75, # 20 p. 2451 - 2462 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

rat cortex synaptosomal membrane-enriched fraction

Method (Pharmacological Data)

the ability of title comp. to bind to serotonin receptors determined by measuring cAMP induced by serotonin; samples incubated for 2 min at room temp. in the presence of isobutyl methylxanthine; incubation with iodinated tracer; gamma spectrometry

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

10.0 nmol/l

Reference

Locher, Christopher P.; Ruben, Peter C.; Gut, Jiri; Rosenthal, Philip J.

Antimicrobial Agents and Chemotherapy, 2003 , vol. 47, # 12 p. 3806 - 3809 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antimalarial

Species or TestSystem (Pharmacological Data)

Plasmodium falciparum

Method

parasites in the schizont stage (0.1 percent parasitemia, 1 percent hematocrit) incubated with title comp. and <3H>hypoxanthine for 72

94 of 174

95 of 174

96 of 174

(Pharmacological Data)

h; <3H>hypoxanthine incorporation determined

Further Details (Pharmacological Data)

P. falciparum: Falciparum Uganda Palo Alto (FUP, mefloquine resistant) strain

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.70 μmol/l

Results

title comp. in dose-dependent manner inhibited growth of plasmodium

Reference

Locher, Christopher P.; Ruben, Peter C.; Gut, Jiri; Rosenthal, Philip J.

Antimicrobial Agents and Chemotherapy, 2003 , vol. 47, # 12 p. 3806 - 3809 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

CHO cells expressing human 5-HT1A receptor

Kind of Dosing (Pharmacological Data)

title comp. admin. as HCl salt

Method (Pharmacological Data)

recombinant 5-hydroxytryptamine receptor subtype; competition binding assay; <3H>8-OH-DPAT (0.25 nmol/l) used as radioligand; TrisHCl buffer, pH 7.4; incubated for 1 h at 27 deg C; radioactivity counted on β-counter

Further Details (Pharmacological Data)

positive control: (R)-8-hydroxy-2-(di-n-propylamino)tetralin ((R)-8-OH-DPAT; IC50 = 0.52 nmol/l)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

4230 nmol/l

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

rat 5-HT2A receptor (cerebral cortex)

Kind of Dosing (Pharmacological Data)

title comp. admin. as HCl salt

Method (Pharmacological Data)

5-hydroxytryptamine receptor subtype; competition binding assay; <125I>(+/-)-DOI (80 pmol/l) used as radioligand; incubated for 1 h, 23 deg C; nonspecific binding determined using 10 μmol/l methiothepin; radioactivity determined by liquid scintillation

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.33 nmol/l

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

intracellular calcium mobilization; effect on

97 of 174

98 of 174

99 of 174

Species or TestSystem (Pharmacological Data)

rat vascular smooth muscle cells (A7r5)

Kind of Dosing (Pharmacological Data)

title comp. stored in 50 percent DMSO/50 percent ethanol and diluted 1:50 in 20 percent DMSO/20 percent ethanol; HCl salt used

Method (Pharmacological Data)

cells cultured in 96-well plate; title comp. added; loaded in with calcium-sensitive dye; incubated for 1 h at 23 deg C; mobilization of intracellular calcium studied using fluorescence imaging plate reader

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

30.2 nmol/l

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

CHO cells expressing human 5-HT2A receptor

Kind of Dosing (Pharmacological Data)

title comp. admin. as HCl salt

Method (Pharmacological Data)

cloned 5-hydroxytryptamine receptor subtype; competition binding assay; <125I>(+/-)-DOI (0.2 nmol/l) used as radioligand; incubated for 15 min at 37 deg C; radioactivity determined by liquid scintillation counting

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.96 nmol/l

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

CHO cells expressing human 5-HT2B receptor

Kind of Dosing (Pharmacological Data)

title comp. admin. as HCl salt

Method (Pharmacological Data)

cloned human 5-hydroxytryptamine receptor subtype; competition binding assay; <125I>(+/-)-DOI (0.2 nmol/l) used as radioligand; incubated for 15 min at 37 deg C; radioactivity determined by liquid scintillation counting

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

12 nmol/l

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

100 of 174

101 of 174

Species or TestSystem (Pharmacological Data)

CHO cells expressing human 5-HT2C receptor

Kind of Dosing (Pharmacological Data)

title comp. admin. as HCl salt

Method (Pharmacological Data)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

7.2 nmol/l

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ocular pressure; reduction of

Species or TestSystem (Pharmacological Data)

Macaca fascicularis, cynomolgus monkey

Sex

male and female

Route of Application

ocular

Concentration (Pharmacological Data)

150 μg

Kind of Dosing (Pharmacological Data)

HCl salt of title comp. in PBS vehicle containing 0.01 percent benzalkonium chloride, 0.01 percent disodium EDTA, 0.1 percent polysorbate 80, 0.8 percent hydroxypropylmethylcellulose (pH 7.4) admin.

Method (Pharmacological Data)

conscious monkey with ocular hypertension; title comp. instilled to eye with higher intraocular pressure (other eye as control); intraocular pressure measured with pneumatonometer prior to treatment and at 1, 3, and 6 h

Further Details (Pharmacological Data)

IOP: intraocular pressure; control group: phosphate-buffered saline (PBS), pH 7.4; compound is considered efficacious in hypertensive eyes if there is a decrease from baseline IOP of at least 20 percent topical administration

Results

title comp. resulted in potent reduction of IOP (31 percent); diagram

Reference

May, Jesse A.; McLaughlin, Marsha A.; Sharif, Najam A.; Hellberg, Mark R.; Dean, Thomas R.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 306, # 1 p. 301 - 309 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Chinese Hamster Ovary (CHO) cells

Concentration (Pharmacological Data)

Ca. 0.01 - 1000 nmol/l

Method (Pharmacological Data)

h5-HT2B expressed in CHO cells; (3H)PI depletion (pEC50, Emax) determined by microplate scintillation counter after 30 min incubation of (3H)myo-inositol-labelled cells at 37 deg C, binding affinity (pKi) by competition binding with 1 nM (3H)mesulergine

Further Details (Pharmacological Data)

h5-HT2B = human 5-HT2B receptors; PI = phosphatidylinositol; EC50 = concentration of title comp. that produced a half-maximal response; Ki = inhibition constant; (3H)PI depletion expressed relative to effect of 10 μM 5-HT; title comp. is an agonist

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological

7.98 dimensionless

Data)

102 of 174

103 of 174

104 of 174

Results

dose-dependent (3H)PI depletion, Emax = 103.6 percent; pKi = 8.15

Reference

Cussac, Didier; Newman-Tancredi, Adrian; Quentric, Yann; Carpentier, Nathalie; Poissonnet, Guillaume; Parmentier, JeanGilles; Goldstein, Solo; Millan, Mark J.

Naunyn-Schmiedeberg's Archives of Pharmacology, 2002 , vol. 365, # 3 p. 242 - 252 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Chinese Hamster Ovary (CHO) cells

Concentration (Pharmacological Data)

Ca. 0.01 - 100 nmol/l

Method (Pharmacological Data)

h5-HT2C expressed in CHO cells; (3H)PI depletion (pEC50, Emax) determined by microplate scintillation counter after 20 min incubation of (3H)myo-inositol-labelled cells at 37 deg C, binding affinity (pKi) by competition binding with 1 nM (3H)mesulergine

Further Details (Pharmacological Data)

h5-HT2C = human 5-HT2C receptors; PI = phosphatidylinositol; EC50 = concentration of title comp. that produced a half-maximal response; Ki = inhibition constant; (3H)PI depletion expressed relative to effect of 10 μM 5-HT; title comp. is an agonist

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

8.55 dimensionless

Results

dose-dependent (3H)PI depletion, Emax = 101.6 percent; pKi = 7.73

Reference

Cussac, Didier; Newman-Tancredi, Adrian; Quentric, Yann; Carpentier, Nathalie; Poissonnet, Guillaume; Parmentier, JeanGilles; Goldstein, Solo; Millan, Mark J.

Naunyn-Schmiedeberg's Archives of Pharmacology, 2002 , vol. 365, # 3 p. 242 - 252 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

vasodilative

Species or TestSystem (Pharmacological Data)

mongrel dog

Sex

male and female

Route of Application

intrarenal

Kind of Dosing (Pharmacological Data)

infused into the renal artery at a rate of 5 μg/kg*min for 30 min

Method (Pharmacological Data)

mean blood pressure, renal blood flow, and renal vasoconstriction resistance were monitored throughout the experiment; dialysate was collected via microdialysis probe implanted into the renal cortex; dialysate was assessed for NO2/NO3 and cGMP levels

Further Details (Pharmacological Data)

anesthetized dogs; further investigations on mechanism of the effect performed after the pretreatment with either saprogrelate or LNAME (100 μg/kg*min each) for 30 and 60 min, respectively; L-NAME = Nw-nitro-L-arginine methyl ester

Results

title comp. increased the renal blood flow and decreased the renal vascular resistance; these effects were accompanied by significant increases in both NO2/NO3 and cGMP levels; all effects were abolished after pretreatment with saprogrelate or L-NAME

Reference

Tian, Run-Xian; Kimura, Shoji; Kondou, Naoki; Fujisawa, Yoshihide; Zhou, Ming-Sheng; Yoneyama, Hirohito; Kosaka, Hiroaki; Rahman, Matlubur; Nishiyama, Akira; Abe, Youichi

European journal of pharmacology, 2002 , vol. 437, # 1-2 p. 79 - 84 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

diuretic

Species or TestSystem (Pharmacological Data)

mongrel dog

105 of 174

106 of 174

107 of 174

Sex

male and female

Route of Application

intrarenal

Kind of Dosing (Pharmacological Data)

infused into the renal artery at a rate of 5 μg/kg*min for 30 min

Method (Pharmacological Data)

glomerular filtration rate (GFR) measurements based on creatinine clearance (loading dose of 100 mg/kg), urine flow, and Na(1+) urinary excretion rate were monitored throughout the experiment

Further Details (Pharmacological Data)

Results

title comp. significantly increased the GFR, urine flow, and Na(1+) urinary excretion rate; all effects were abolished after pretreatment with saprogrelate or L-NAME (table)

Reference

Tian, Run-Xian; Kimura, Shoji; Kondou, Naoki; Fujisawa, Yoshihide; Zhou, Ming-Sheng; Yoneyama, Hirohito; Kosaka, Hiroaki; Rahman, Matlubur; Nishiyama, Akira; Abe, Youichi

European journal of pharmacology, 2002 , vol. 437, # 1-2 p. 79 - 84 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

vasoconstrictive

Species or TestSystem (Pharmacological Data)

mongrel dog

Sex

male and female

Route of Application

intraarterial

Concentration (Pharmacological Data)

0.31 - 10 μg/min

Method (Pharmacological Data)

dogs (15-30 kg) anaesthetized (sodium pentobarbitone); bilateral cervical vagosympathectomy; 1 min intracarotid infusion of title comp.

Further Details (Pharmacological Data)

internal carotid blood flow; antagonists: GR127935 (30 μg/kg), ritanserin (100 μg/kg), ketanserin (100 μg/kg); 5-HT1B/1D and 5-HT2A receptors

Results

dose-response curve of internal carotid blood flow (diagram); effect of antagonists (diagrams)

Reference

Centurion, David; Ortiz, Mario I; Sanchez-Lopez, Araceli; De Vries, Peter; Saxena, Pramod R; Villalon, Carlos M

British Journal of Pharmacology, 2001 , vol. 132, # 5 p. 983 - 990 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

HEK293 cells expressing rTAR1

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

cells incubated in KRH with 100 μmol/l 3-isobutyl-1-methylxanthine and title comp. for 1 h at 37 deg C; cAMP content measured using competitive binding of <3H>cAMP to a cAMP-binding protein

Further Details (Pharmacological Data)

HEK: human embryonic kidney; rTAR1: rat trace amine receptor 1; reference comp.: forskolin; KRH: Krebs-Ringer-HEPES buffer

Results

title comp. induced cAMP production acting as agonist (diagram)

Reference

Bunzow; Sonders; Arttamangkul; Harrison; Zhang; Quigley; Darland; Suchland; Pasumamula; Kennedy; Olson; Magenis; Amara; Grandy

Molecular Pharmacology, 2001 , vol. 60, # 6 p. 1181 - 1188 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

108 of 174

109 of 174

110 of 174

Species or TestSystem (Pharmacological Data)

human embryonic kidney 293 cells

Method (Pharmacological Data)

membranes of cells stably expressing wild type human 5-HT2A receptors were incubated with title comp. and 1 nmol/l <3H>ketanserin; binding affinity of title comp. to 5-HT2A receptors was determined

Further Details (Pharmacological Data)

non-specific binding was determined after incubation with 10 μmol/l 5-hydroxytryptamine

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

8.24 dimensionless

Reference

Wurch, Thierry; Palmier, Christiane; Pauwels, Petrus J.

Biochemical Pharmacology, 2000 , vol. 59, # 9 p. 1117 - 1121 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

COS-7 cells

Method (Pharmacological Data)

membranes of cells transiently expressing wild type human 5-HT1B receptors were incubated with title comp. and 1 nmol/l <3H>GR 125743; binding affinity of title comp. to 5-HT1B receptors was determined

Further Details (Pharmacological Data)

non-specific binding was determined after incubation with 10 μmol/l 5-hydroxytryptamine; <3H>GR 125743: <3H>N-<4-methoxy-3-(4methylpiperazin-1-yl)phenyl>-3-methyl-4-(4-pyridil)-benzamide

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

< 5 dimensionless

Reference

Wurch, Thierry; Palmier, Christiane; Pauwels, Petrus J.

Biochemical Pharmacology, 2000 , vol. 59, # 9 p. 1117 - 1121 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

COS-7 cells

Method (Pharmacological Data)

membranes of cells transiently expressing 5-HT1B/2A receptors were incubated with title comp. and 1 nmol/l <3H>GR 125743; binding affinity of title comp. to 5-HT1B/2A receptors was determined

Further Details (Pharmacological Data)

non-specific binding was determined after incubation with 10 μmol/l 5-hydroxytryptamine; <3H>GR 125743: <3H>N-<4-methoxy-3-(4methylpiperazin-1-yl)phenyl>-3-methyl-4-(4-pyridil)-benzamide

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

< 5 dimensionless

Reference

Wurch, Thierry; Palmier, Christiane; Pauwels, Petrus J.

Biochemical Pharmacology, 2000 , vol. 59, # 9 p. 1117 - 1121 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

111 of 174

112 of 174

Species or TestSystem (Pharmacological Data)

COS-7 cells

Method (Pharmacological Data)

membranes of cells transiently expressing 5-HT1B/2Aδ44 receptors were incubated with title comp. and 1 nmol/l <3H>GR 125743; binding affinity of title comp. to 5-HT1B/2Aδ44 receptors was determined

Further Details (Pharmacological Data)

non-specific binding was determined after incubation with 10 μmol/l 5-hydroxytryptamine; <3H>GR 125743: <3H>N-<4-methoxy-3-(4methylpiperazin-1-yl)phenyl>-3-methyl-4-(4-pyridil)-benzamide

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

< 5 dimensionless

Reference

Wurch, Thierry; Palmier, Christiane; Pauwels, Petrus J.

Biochemical Pharmacology, 2000 , vol. 59, # 9 p. 1117 - 1121 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

secretion stimulant

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 - 10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. dissolved in saline

Method (Pharmacological Data)

rats admin. with title comp.; blood collected from caudal venacava; time-course and dose-response studies of title comp. on both plasma glucose levels and glucagon levels detd.; glucagon levels detd. by radioimmunoassay 15 min after title comp. admin.

Further Details (Pharmacological Data)

control: saline; further studies on effect of adrenomedullation, with ritanserin and ketanserin on title comp.-induced hyperglucagonemia in rats

Results

title comp. elevated plasma glucose and glucagon levels in dose-dependent manner, reached max. 15 min after admin. at 10 mg/kg; effect completely abolished by adrenomedullation; ketanserin and ritanserin apparently reduced title comp. effect; diagrams

Reference

Sugimoto; Yamada

Biological and pharmaceutical bulletin, 2000 , vol. 23, # 12 p. 1521 - 1523 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

drug dependence

Endpoint of Effect (Pharmacological Data)

50 percent DOI-lever responding produced

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.1 - 0.4 mg/kg

Kind of Dosing (Pharmacological Data)

as hydrochloride 30 min before testing

Method

in vivo; two-lever drug discrimination assay; 2,5-dimethoxy-4-iodoamphetamine(DOI)-trained rats (200-220 g) maintained at 22-24 deg

113 of 174

114 of 174

(Pharmacological Data)

C, 12-h light/dark cycle and 40-50 percent relative humidity with free access to water and rationed amount of supplemental feed

Further Details (Pharmacological Data)

percent of rats selecting NOI lever ( percent SDL) for eachdose of title comp. determined; degree of substitution determined by max. percentADL for all doses of title comp.; no substitution: <= 59 percent SDL; partial substitution: 60-79 percent SDL; complete substitution: > 80 percent SDL

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

0.12 mg/kg

Results

dose (mg/kg)/ percent SDL: 0.1/56, 0.2/89, 0.4/100 - full substitution

Reference

Gerasimov, Madina; Marona-Lewicka, Danuta; Kurrasch-Orbaugh, Deborah M.; Qandil, Amjad M.; Nichols, David E.

Journal of Medicinal Chemistry, 1999 , vol. 42, # 20 p. 4257 - 4263 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.27 mg/kg

Kind of Dosing (Pharmacological Data)

single dose in 1 ml/kg saline

Method (Pharmacological Data)

250-350 g rats (12 h light/dark cycle); after title comp.+0.75-10.125 mg/kg s.c. phencyclidine (PCP) tested in Behavioral Pattern Monitor for 120 min

Further Details (Pharmacological Data)

locomotor activity assessed by photocells; complexity of spatial motion (Sd) analyzed based on fractal geometry; title comp. effect on LA, Sd alone or with PCP studied

Results

LA, Sd decreased; with PCP: LA profoundly enhanced; Sd changed (diagram)

Reference

Krebs-Thomson, Kirsten; Lehmann-Masten, Virginia; Naiem, Shahrouz; Paulus, Martin P.; Geyer, Mark A.

European Journal of Pharmacology, 1998 , vol. 343, # 2-3 p. 135 - 143 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

Ca. 3E-09 - 3E-06 mol/l

Method (Pharmacological Data)

ability of title comp. to activate PLC-mediated IP accumulation studied; cells labeled with 1 μCi/ml myo-<3H>inositol (24 h, 37 deg C) incubated with title comp. for 10 min; mono-, di-, triphosphates of inositol separated by ion exchange chromatography

Further Details (Pharmacological Data)

radioactivity counted by liquid scintillation; cells expressing human 5-HT2C receptors; 5-HT: 5-hydroxytryptamine; PLC: phospholipase C; IP: inositol phosphates; 5-HT used as reference comp. (pEC = 7.43); Emax: maximal response

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

6.72 dimensionless

Results

Emax title comp./Emax 5-HT = 0.61 (table)

115 of 174

116 of 174

117 of 174

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

Ca. 3E-09 - 3E-06 mol/l

Method (Pharmacological Data)

ability of title comp. to activate PLA2-mediated arachidonic acid release studied; cells labeled with 0.1 μCi/ml <14C>arachidonic acid (4 h, 37 deg C) incubated with title comp. for 10 min; radioactivity measured by liquid scintillation counting

Further Details (Pharmacological Data)

cells expressing human 5-HT2C receptors; 5HT: 5-hydroxytryptamine; PLA2: phospholipase A2; 5-HT used as reference comp. (pEC50 = 7.34); Emax: maximal response

Type (Pharmacological Data)

pEC50

Value of Type (Pharmacological Data)

6.8 dimensionless

Results

Emax title comp./Emax 5-HT = 0.97 (table)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

ability of title comp. to activate <14C>AA release and <3H>IP accumulation studied after 15-min pretreatment with inhibitors: 100 μmol/l mepacrine (PLA2), 10 μmol/l U73122, and 10 μmol/l ET-18-OCH3 (PLC)

Further Details (Pharmacological Data)

cells expressing human 5-HT2C receptors; 5-HT: 5-hydroxytryptamine; PLA2 and PLC: phospholipases A2 and C; AA: arachidonic acid; ET18-OCH3: 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine

Results

title comp.-induced AA-release was completely abolished by PLA2 inhibitor and was not altered by PLC inhibitors; IP accumulation was reduced by PLC inhibitors (ca. 50 percent) and slightly reduced by PLA2 inhibitor (figure)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

ability of title comp.to activate <14C>AA release studied after 5 - 30 min pretreatment with inhibitors: PLA2 mepacrine (100 μol/l), PLC U73122 and ET-18-OCH3 (10 μmol/l), PKC staurosporine (1 μmol/l), Ca(2+) chelator BAPTA-AM (30 μmol/l)

Further Details (Pharmacological Data)

cells expressing human 5-HT2C receptors; 5-HT: 5-hydroxytryptamine; PLA2 and PLC: phospholipases A2 and C, resp.; AA: arachidonic acid; ET-18-OCH3: 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine

118 of 174

119 of 174

120 of 174

Results

title comp.-induced AA-release was completely abolished by PLA2 inhibitor and was not altered by PLC and PKC inhibition and Ca(2+) chelation (figure)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary 1C19 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

ability of title comp. to activate <3H>IP accumulation studied after 5 - 30 min pretreatment with inhibitors: PLA2 mepacrine (100 μol/l), PLC U73122 and ET-18-OCH3 (10 μmol/l), PKC staurosporine (1 μmol/l)

Further Details (Pharmacological Data)

cells expressing human 5-HT2C receptors; 5-HT: 5-hydroxytryptamine; PLA2 and PLC: phospholipases A2 and C, resp.; IP: inositol phosphates; ET-18-OCH3: 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine

Results

title comp.-induced IP accumulation was reduced by PLC inhibitors (ca. 50 percent), slightly reduced by PLA2 inhibitor, and was not altered by PKC inhibition (figure)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

radioactivity counted; cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; PLC: phospholipase C; IP: inositol phosphates; reference comp.: 5-HT; Emax: maximal response; further investigation with PKC inhibitor staurosporine

Results

Emax title comp./Emax 5-HT ca. 0.35; effect was enhanced by staurosporine (figure)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

ability of title comp. to activate PLA2-mediated arachidonic acid (AA) release studied; cells labeled with 0.1 μCi/ml <14C>AA (4 h, 37 deg C) incubated with title comp. for 10 min; radioactivity measured by liquid scintillation counting

Further Details (Pharmacological Data)

cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; PLA2: phospholipase A2; 5-HT used as reference comp.; Emax: maximal response; further investigation with PKC inhibitor staurosporine and chelator of Ca(2+) BAPTA-AM

Results

Emax title comp./Emax 5-HT ca. 0.65; title comp.-induced AA release was not altered by PKC inhibition or Ca(2+) chelation (figure)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104

Title/Abstract Full Text View citing articles Show Details

121 of 174

122 of 174

123 of 174

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary FA4 cells

Concentration (Pharmacological Data)

1 μmol/l

Method (Pharmacological Data)

ability of title comp. to increase Ca(2+) conc. studied; cells loaded with Fura-2; intracellular Ca(2+) conc. determined by measuring fluorescence (340/380 nm)

Further Details (Pharmacological Data)

cells expressing human 5-HT2A receptors; 5-HT: 5-hydroxytryptamine; 5-HT used as reference comp.; Emax: maximal response; further investigation with Ca(2+) chelator BAPTA-AM

Results

Emax title comp./Emax 5-HT ca. 0.45; effect was completely blocked by BAPTA-AM (figure)

Reference

Berg, Kelly A.; Maayani, Saul; Goldfarb, Joseph; Scaramellini, Clare; Leff, Paul; Clarke, William P.

Molecular Pharmacology, 1998 , vol. 54, # 1 p. 94 - 104 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

spasmogenic

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intracerebral

Concentration (Pharmacological Data)

2.8 - 28 nmol

Kind of Dosing (Pharmacological Data)

title comp. administered at rate 0.5 μl/min in total volume 0.5 μl/side

Method (Pharmacological Data)

title comp. administered directly into medial prefrontal cortex; number of head-twitches observed in 5-min period for 30 min after title comp. administration

Further Details (Pharmacological Data)

further investigation on mechanism of action with 5-HT2-antagonists: ketanserin, MDL 100907, SDZ SER 082; 5-HT1A agonists: 8OHDPAT, WAY 100635

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

12.8 nmol

Results

title comp. produced dose-dependent head-twitch response with a duration of 30 min (diagram); title comp. effect mediated with 5-HT2A receptors activation

Reference

Willins, David L.; Meltzer, Herbert Y.

Journal of Pharmacology and Experimental Therapeutics, 1997 , vol. 282, # 2 p. 699 - 706 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; inhib. of

Species or TestSystem (Pharmacological Data)

IIBCE rat brain mitochondrial monoamine oxidase B

Sex

male

Concentration (Pharmacological

0.01 - 100 μmol/l

Data)

124 of 174

125 of 174

Kind of Dosing (Pharmacological Data)

in distilled water

Method (Pharmacological Data)

MAO-B activity determined by HPLC with electrochemical detection after incubation with selective substrate of DMAPEA in presence of title comp. at 37 deg C for 5 min, pH 7.4; DMAPEA and its MAO-B metabolite DMAPAA used to calculate MAO-B activity

Further Details (Pharmacological Data)

MAO-B = monoamine oxidase B; DMAPEA = 4-dimethylaminophenethylamine, 5 μmol/l; DMAPAA = 4-dimethylaminophenylacetic acid

Comment (Pharmacological Data)

No effect

Reference

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; inhib. of

Species or TestSystem (Pharmacological Data)

IIBCE rat brain mitochondrial monoamine oxidase A

Sex

male

Concentration (Pharmacological Data)

0.01 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in distilled water

Method (Pharmacological Data)

MAO-A activity determined by HPLC with electrochemical detection after incubation with selective substrate of 5-HT in presence of title comp. at 37 deg C for 10 min, pH 7.4; 5-HT and its MAO-A metabolite 5-HIAA used to calculate MAO-A activity

Further Details (Pharmacological Data)

MAO-A = monoamine oxidase A; 5-HT = serotonin, 2.5 μmol/l; 5-HIAA = 5-hydroxyindoleacetic acid

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

43 μmol/l

Reference

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Hartley guinea pig brain

Concentration (Pharmacological Data)

10 μmol/l

Method (Pharmacological Data)

whole brain dissected, sectioned and mounted on glass slides; effect of title comp. on (35S)GTPγS binding studied after 60 min incubation at 30 deg C by light microscopic autoradiography and image analysis

Further Details (Pharmacological Data)

title comp. is a 5-HT2A/2C receptor agonist; GTPγS: guanosine-5'-O-(3-thio)triphosphate, 0.04 nM

Comment (Pharmacological Data)

No effect

Reference

Waeber; Moskowitz

Molecular pharmacology, 1997 , vol. 52, # 4 p. 623 - 631

Title/Abstract Full Text View citing articles Show Details

126 of 174

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

calf striatum

Method (Pharmacological Data)

striatal homogenates incubated with title comp. and 1 nmol/l <3H>nemonapride for 4 h at 22 deg C in presence of 10 μmol/l (-)-sulpiride and pentazocine to block D2, D3, D4 and σ components of <3H>nemonapride binding

Further Details (Pharmacological Data)

specific binding defined by 10 μmol/l haloperidol

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

127 of 174

128 of 174

> 10 μmol/l

Reference

Helmeste, Daiga M.; Tang, Siu W.; Li, Ming; Fang, Hong

Naunyn-Schmiedeberg's Archives of Pharmacology, 1997 , vol. 356, # 1 p. 17 - 21 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Dunkin-Hartley guinea pig

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.1 - 6 mg/kg

Method (Pharmacological Data)

guinea-pig weight 390-450 g; housed individually in racks with free access to food and water; saline-treated control-group

Further Details (Pharmacological Data)

effect of ketanserin (1 mg/kg, s.c.); animals scored for wet dog shakes for 30 min

Results

dose-related increase in head and wet dog shakes with a reduced response at the top dose; antagonism of title comp.-induced behavioural effects by the pretreatment with ketanserin

Reference

Mundey; Fletcher; Marsden

British Journal of Pharmacology, 1996 , vol. 117, # 4 p. 750 - 756 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

calcium metabolism regulator

Species or TestSystem (Pharmacological Data)

human pulmonary artery endothelial (PAE) cells

Concentration (Pharmacological Data)

1E-07 - 0.0003 mol/l

Method (Pharmacological Data)

cells preloaded with fura-2-AM; intracellular free Ca(2+), <Ca(2+)i> measured by fluorescence with the whole cell patch-clamp technique

Further Details (Pharmacological Data)

effect studied without/with extracellular Ca

Results

conc.-dependent increase of <Ca(2+)i> (pD2 = 5.66) (graph)

Reference

Ullmer; Boddeke; Schmuck; Lubbert

British Journal of Pharmacology, 1996 , vol. 117, # 6 p. 1081 - 1088 Title/Abstract Full Text View citing articles Show Details

129 of 174

130 of 174

131 of 174

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

human pulmonary artery endothelial (PAE) cells

Concentration (Pharmacological Data)

1E-10 - 1E-05 mol/l

Method (Pharmacological Data)

PAE cells incub. with <3H>-myo-inositol; adenylate cyclase activity (ACA) measured by assaying <3H>-ATP, <3H>cAMP production by incub. with <2-3H>-adenine

Further Details (Pharmacological Data)

title comp. effect on ACA studied (graph)

Comment (Pharmacological Data)

No effect

Reference

Ullmer; Boddeke; Schmuck; Lubbert

British Journal of Pharmacology, 1996 , vol. 117, # 6 p. 1081 - 1088 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

mutant A5.46S 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

120 nmol/l

Reference

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.

Molecular Pharmacology, 1996 , vol. 50, # 1 p. 34 - 42 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

wild-type 5-HT2C receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

41 nmol/l

Reference

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.

Molecular Pharmacology, 1996 , vol. 50, # 1 p. 34 - 42 Title/Abstract Full Text View citing articles Show Details

132 of 174

133 of 174

134 of 174

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

mutant S5.46A 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

51 nmol/l

Reference

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.

Molecular Pharmacology, 1996 , vol. 50, # 1 p. 34 - 42 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

wild-type 5-HT2A receptors expressed in COS-1 cells

Method (Pharmacological Data)

incubation at 37 deg C for 1 h in Tris*HCl buffer solution

Further Details (Pharmacological Data)

Ki: binding affinity

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

15 nmol/l

Reference

Almaula, Niva; Ebersole, Barbara J.; Ballesteros, Juan A.; Weinstein, Harel; Sealfon, Stuart C.

Molecular Pharmacology, 1996 , vol. 50, # 1 p. 34 - 42 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

NIH 3T3 cell membranes expressing human 5HT2A receptors

Concentration (Pharmacological Data)

1E-11 - 1E-05 mol/l

Method (Pharmacological Data)

in vitro; effect on agonist or antagonist binding assayed; 3 nM <3H>5-HT, 1nM <3H>DOB or 1 nM <3H>ketanserin with spec. act.: 27.9, 16, 61 Ci/mmol respectively; assay buffer (pH 7.4); room temp.; incubation time 1 h

Further Details (Pharmacological Data)

radioligand displacement from 5-HT2A receptors determined by scintillation spectroscopy; DOB: 4-bormo-2,5dimethoxyphenylisopropylamine; 5-HT: serotonin

Results

pKi values for <3H>5-HT, <3H>DOB and <3H>ketanserin displacement were 9.22, 8.78 and 7.97 respectively

Reference

Sleight, Andrew J.; Stam, Nico J.; Mutel, Vincent; Vanderheyden, Patrick M. L.

Biochemical Pharmacology, 1996 , vol. 51, # 1 p. 71 - 76 Title/Abstract Full Text View citing articles Show Details

135 of 174

136 of 174

137 of 174

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Spraque-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.05 - 4 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in physiological saline; injection at 2 ml/kg

Method (Pharmacological Data)

animal weight 280-320 g; rats were administered by drugs; locomotor activity measurement; topographical analysis of locomotor activity

Further Details (Pharmacological Data)

variables calculated: locomotor activity; peripheral locomotion; rearing; forward locomotion

Results

marked increase in forward locomotion of the rats; the stereotyped forward locomotion less pronounced as by 8-OH-DPAT

Reference

Hillegaart; Estival; Ahlenius

European Journal of Pharmacology, 1996 , vol. 295, # 2-3 p. 155 - 161 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

diabetogenic

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 - 10 mg/kg

Method (Pharmacological Data)

plasma glucose levels measured by methods of Sugimoto et al.: Jpn. J. Pharmacol. 60, 145

Results

at end above 5 mg/kg produced significant hyperglycemia that peaked ca. 15 min after dosing

Reference

Sugimoto, Yumi; Yamada, Jun; Yoshikawa, Tomoko; Horisaka, Kazuyoshi

European Journal of Pharmacology, 1996 , vol. 307, # 1 p. 75 - 80 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.32 mg/kg

Kind of Dosing (Pharmacological Data)

single dose

Method

200-250 g rats (12 h light:dark cycle); without/with 50 mg/kg s.c. corticosterone (-/+C) inj. twice daily for 4 d; after C inj. single dose of

138 of 174

(Pharmacological Data)

title comp.; open field behavior (total visits, TV; visits innerfield, VI; travelled distance, TD) observed

Further Details (Pharmacological Data)

TV, VI, TD scored in 100x100 cm square EthoVision apparatus; walking pattern recorded with X-Y plotter; total number of faecal pellets (FP) also counted; title comp. effect on TV, VI, TD, FP studied

Comment (Pharmacological Data)

No effect

Reference

Berendsen, Hemmie H.G.; Kester, Robert C.H.; Peeters, Bernard W.M.M.; Broekkamp, Chris L.E.

European Journal of Pharmacology, 1996 , vol. 308, # 2 p. 103 - 111 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

139 of 174

Method (Pharmacological Data)

recombinant human 5-HT1Dβ receptor subtype stably expressed in cells; effect on 5-hydroxytryptamine (5-HT)-mediated inhibition of forskolin-stimulated cAMP accumulation; radioimmunoassay

Further Details (Pharmacological Data)

apparent dissociation constant (Kb) by Schild equation from concentration-response curves of 5-HT generated in absence and presence of title comp.

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1169 nmol/l

Reference

Zgombick, John M.; Schechter, Lee E.; Adham, Nika; Kucharewicz, Stefan A.; Weinshank, Richard L.; Branchek, Theresa A.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 3 p. 226 - 236 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

140 of 174

Y-1 adrenocortical tumor cells

Method (Pharmacological Data)

recombinant human 5-HT1Dβ receptor subtype stably expressed in cells; potency to inhibit forskolin-stimulated cAMP accumulation; radioimmunoassay

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

534 nmol/l

Results

partial agonist activity; intrinsic acitivity 0.45

Reference

Zgombick, John M.; Schechter, Lee E.; Adham, Nika; Kucharewicz, Stefan A.; Weinshank, Richard L.; Branchek, Theresa A.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 3 p. 226 - 236 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

NIH-3T3 fibroblast

Method (Pharmacological Data)

recombinant human 5-HT1Dα receptor subtype stably expressed in fibroblasts; potency to inhibit forskolin-stimulated cAMP accumulation; radioimmunoassay

Type (Pharmacological Data)

EC50

141 of 174

142 of 174

143 of 174

Value of Type (Pharmacological Data)

346 nmol/l

Results

full agonist activity; intrinsic acitivity 0.97

Reference

Zgombick, John M.; Schechter, Lee E.; Adham, Nika; Kucharewicz, Stefan A.; Weinshank, Richard L.; Branchek, Theresa A.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 3 p. 226 - 236 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

growth stimulation

Species or TestSystem (Pharmacological Data)

rat C6-glial cells

Method (Pharmacological Data)

cells expressing human 5-HT1D receptors; cultured in supplemented DMEM; 3000 cells treated with title comp. for 6 days; cell growth monitored in phase-contrast microscope and quantified by measuring <3H>thymidine incorporation

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

947 nmol/l

Results

title comp. promoted cell growth (diagram)

Reference

Pauwels, Petrus J.; Wurch, Thierry; Palmier, Christiane; Colpaert, Francis C.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 2 p. 136 - 144 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor blocking agent

Species or TestSystem (Pharmacological Data)

rat C6-glial cells

Method (Pharmacological Data)

membrane prepared from cells expressing human 5-HT1D receptors; incubed with <3H>5-carboxamidotryptamine (0.5 nM) in presence of title comp.

Further Details (Pharmacological Data)

IC50-value calculated as Ki-value (inhibition constant)

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

347 nmol/l

Reference

Pauwels, Petrus J.; Wurch, Thierry; Palmier, Christiane; Colpaert, Francis C.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 2 p. 136 - 144 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuron stimulant

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat piriform cortical interneurons

Sex

male

Concentration (Pharmacological Data)

0.3 - 3 μmol/l

Method (Pharmacological Data)

brain slices perfused with normal ACSF with title comp. for 10 min at 34 deg C before treatment with 5-HT or NE or AMPA; extracellular recordings conducted from interneurons (layer III) using glass microelectrodes; firing rates recorded

Further Details (Pharmacological

5-HT: 5-hydroxytryptamine; NE: norepinephrine; AMPA: α-amino-3-hydroxy-5-methyl-4-isoxazolepropionate; ACSF: artificial cerebrospinal fluid

Data)

144 of 174

145 of 174

146 of 174

Results

3 μmol/l title comp. decreased excitatory effect of 30 and 100 μmol/l 5-HT to 62 percent and 87 percent of control, but not effect of 100 μmol/l NE; title comp. increased excitatory effect of AMPA (figure, table)

Reference

Marek, Gerard J.; Aghajanian, George K.

Journal of Pharmacology and Experimental Therapeutics, 1996 , vol. 278, # 3 p. 1373 - 1382 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuron stimulant

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat piriform cortical interneurons

Sex

male

Concentration (Pharmacological Data)

0.3 - 10 μmol/l

Method (Pharmacological Data)

brain slices perfused with normal ACSF with title comp. for 10 min at 34 deg C; extracellular recordings conducted from interneurons (layer III) using glass microelectrodes; firing rates recorded

Further Details (Pharmacological Data)

5-hydroxytryptamine (5-HT) as reference comp.; ACSF: artificial cerebrospinal fluid; further investigation in presence of 5-HT2A receptor antagonist MDL 100,907

Results

title comp. induced concentration-dependent increase in firing rate of almost every cell excited by 5-HT; excitations achieved by 1 and 3 μmol/l title comp. were 55 percent and 49 percent of effect of 100 μmol/l 5-HT; effect was mediated by 5-HT2A receptors

Reference

Marek, Gerard J.; Aghajanian, George K.

Journal of Pharmacology and Experimental Therapeutics, 1996 , vol. 278, # 3 p. 1373 - 1382 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

current; effect on

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat piriform cortical pyramidal neurons

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Method (Pharmacological Data)

brain slices perfused with normal ACSF with title comp. for 10 min at 34 deg C; intracellular recordings and single-electrode voltage clamping at -90 mV conducted in layer II cells, IPSPs recorded

Further Details (Pharmacological Data)

5-hydroxytryptamine (5-HT) as reference comp.; ACSF: artificial cerebrospinal fluid; IPSPs: inhibitory postsynaptic potentials

Results

title comp. induced fewer postsynaptic inhibitory currents than did 5-HT (figure)

Reference

Marek, Gerard J.; Aghajanian, George K.

Journal of Pharmacology and Experimental Therapeutics, 1996 , vol. 278, # 3 p. 1373 - 1382 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

drug interaction

Species or TestSystem (Pharmacological Data)

guinea pig papillary muscle

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Exposure Period (Pharmacological Data)

20 min

Method

tissue superfused with oxygenated Krebs solution; effect of title comp. on 1 μM ketanserin-induced transmembrane action potential (AP)

147 of 174

148 of 174

149 of 174

(Pharmacological Data)

parameters of electrically stimulated preparations

Further Details (Pharmacological Data)

AP parameters: maximum upstroke velocity (Vmax), slopes of repolarization phase (SRP), resting potential (RP), AP duration at 50 and 90 percent repolarization levels (APD50 and APD90,respectively)

Results

alone did not alter significantly SRP, Vmax, and RP; did not alter significantly the prolongation induced by ketanserin

Reference

Le Grand; Talmant; Rieu; Patoiseau; Colpaert; John

Journal of Cardiovascular Pharmacology, 1995 , vol. 26, # 5 p. 803 - 809 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anxiolytic

Species or TestSystem (Pharmacological Data)

Lundbeck mice

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.45 - 7 μmol/kg

Method (Pharmacological Data)

fully automated black and white two-compartment box, 12 h day/night cycle, 21 deg C, 51 percent rel. humidity, air exchange 16 times per h, free access to food and water

Further Details (Pharmacological Data)

5-HT2A/2C receptor agonist, effect on the exploratory behaviour

Results

increased line crossings and time spent in the white compartment significantly wihtout affecting the activity in the black compartment significantly

Reference

Sanchez

Pharmacology and Toxicology, 1995 , vol. 77, # 1 p. 71 - 78 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

mice

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.5 - 1 mg/kg

Kind of Dosing (Pharmacological Data)

in saline

Exposure Period (Pharmacological Data)

15 - 120 min

Method (Pharmacological Data)

chlorpromazine (2.5 mg/kg)- and haloperidol (5 mg/kg)-induced hypothermia; measurement of the rectal temperature

Results

strong inhibition of the chlorpromazine- and haloperidol-induced hypothermia

Reference

Yamada; Sugimoto; Horisaka

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 11 p. 1580 - 1583 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

hypothermia

Species or TestSystem

mice

(Pharmacological Data)

150 of 174

151 of 174

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.5 - 5 mg/kg

Kind of Dosing (Pharmacological Data)

in saline

Exposure Period (Pharmacological Data)

15 - 120 min

Method (Pharmacological Data)

measurement of the rectal temperature; treatment of control animals with saline

Results

significant hypothermia at the dose of 5 mg/kg

Reference

Yamada; Sugimoto; Horisaka

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 11 p. 1580 - 1583 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

convulsant

Species or TestSystem (Pharmacological Data)

mice

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mg/kg

Exposure Period (Pharmacological Data)

30 min

Method (Pharmacological Data)

chlorpromazine (2.5 mg/kg) and haloperidol (5 mg/kg) i.p., respectively

Results

both drugs block head twitch responses

Reference

Yamada; Sugimoto; Horisaka

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 11 p. 1580 - 1583 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

rat frontal cortex homogenate

Exposure Period (Pharmacological Data)

15 min

Method (Pharmacological Data)

radioligand binding; by competition with 0.75 nM <3H>ketanserin; 37 deg C; specific binding defined with 10 μM cinanserin; liquid scintillation analysis

Further Details (Pharmacological Data)

affinity for serotonin 5-HT2A receptors

Type (Pharmacological Data)

Value of Type

21 nmol/l

(Pharmacological Data)

152 of 174

153 of 174

154 of 174

Reference

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.

Medicinal Chemistry Research, 1995 , vol. 5, # 9 p. 651 - 663 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

rat hippocampal homogenate

Exposure Period (Pharmacological Data)

10 min

Method (Pharmacological Data)

radioligand binding; by competition with 0.75 nM <3H>8-OH-DPAT; 37 deg C; specific binding determined with 10 μM 5-HT; liquid scintillation analysis

Further Details (Pharmacological Data)

affinity for serotonin 5-HT1A receptors

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1300 nmol/l

Reference

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.

Medicinal Chemistry Research, 1995 , vol. 5, # 9 p. 651 - 663 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

neurotransmitter uptake inhibition

Species or TestSystem (Pharmacological Data)

rat brain synaptosome

Exposure Period (Pharmacological Data)

5 min

Method (Pharmacological Data)

radioligand binding; specific uptake defined in absence of test comp.; 37 deg C; liquid scintillation analysis

Further Details (Pharmacological Data)

inhibition of <3H>serotonin uptake

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

7.60 μmol/l

Reference

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.

Medicinal Chemistry Research, 1995 , vol. 5, # 9 p. 651 - 663 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

neurotransmitter uptake inhibition

Species or TestSystem (Pharmacological Data)

rat brain synaptosome

Exposure Period (Pharmacological Data)

5 min

Method

radioligand binding test; specific uptake defined in absence of test cmpd; 37 deg C; liquid scintillation analysis

(Pharmacological Data)

155 of 174

156 of 174

157 of 174

Further Details (Pharmacological Data)

inhibition of <3H> dopamine and of <3H> norepinephrine uptake

Results

no significant effect up to 50 μM

Reference

Monte, Aaron P.; Marona-Lewicka, Danuta; Cozzi, Nicholas V.; Nelson, David L.; Nichols, David E.

Medicinal Chemistry Research, 1995 , vol. 5, # 9 p. 651 - 663 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

Accumulation

Species or TestSystem (Pharmacological Data)

PVG rat mesangial cells

Concentration (Pharmacological Data)

0 - 10 μmol/l

Method (Pharmacological Data)

rat weight 150-200 g, standard seiving techniques; intracellular cAMP measured by radioimmunoassay using 3-isobutyl-1-methylxanthine to minimize cAMP degradation

Further Details (Pharmacological Data)

forskolin (10 μM) stimulated cAMP accumulation

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

14 nmol/l

Results

65 percent inhibition of cAMP accumulation by the specific 5-HT2 receptor agonist title compound

Reference

Garnovskaya; Nebigil; Arthur; Spurney; Raymond

Molecular Pharmacology, 1995 , vol. 48, # 2 p. 230 - 237 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

increase in cellular acidification rate

Species or TestSystem (Pharmacological Data)

PVG rat mesangial cells

Concentration (Pharmacological Data)

0.1 - 1 μmol/l

Method (Pharmacological Data)

rat weight 150-200 g, standard seiving techniques; microphysiometry

Results

effect antagonized by 5-HT2 receptor antagonists ketanserin (10-1000 nM) and metergoline (100 nM)

Reference

Garnovskaya; Nebigil; Arthur; Spurney; Raymond

Molecular Pharmacology, 1995 , vol. 48, # 2 p. 230 - 237 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological

0.5 mg/kg

Data)

158 of 174

159 of 174

Kind of Dosing (Pharmacological Data)

in 0.9 percent saline 30 min before behavioral recording

Method (Pharmacological Data)

30 young adult rats (60 days, 240-280 g); sexual behavior was recorded 1-2 h after the begining of the dark phase by videotape; receptive females (used to observe) were also Wistar rats (60-90 days, 270 g); saline control

Further Details (Pharmacological Data)

determination of mount- ( the male places his forepaws on the female without pelvic movements) and thrusting frequency (the male places his forepaws on the female, performing repeated deep pelvic thrusting)

Results

title comp. increased mounting and /or mount plus thrusting behavior

Reference

Padoin; Lucion

European Journal of Pharmacology, 1995 , vol. 277, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.5 mg/kg

Kind of Dosing (Pharmacological Data)

in 0.9 percent saline 30 min before behavioral recording

Method (Pharmacological Data)

60 pre-pubertal rats (33-35 days, 80-100 g); sexual behavior was recorded 1-2 h after the begining of the dark phase by videotape; receptive or non-receptive females (used to observe) were also Wistar rats (45-48 days, 80 g); saline control

Further Details (Pharmacological Data)

determination of sniffing-(the male sniff the female's body), genital sniffing-(the male approaches the female and sniffs her anogenital area) and pursuit frequency (the male runs after the female)

Results

title comp. increased the frequency of pursuit and genital sniffing in the presence of receptive females, but not of non-receptive ones, when no mounts or thrustings were recorded

Reference

Padoin; Lucion

European Journal of Pharmacology, 1995 , vol. 277, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.5 mg/kg

Kind of Dosing (Pharmacological Data)

in 0.9 percent saline 30 min before behavioral recording

Method (Pharmacological Data)

60 castrated rats (150 days, 360-430g); sexual behavior was recorded 1-2 h after the begining of the dark phase by videotape; receptive females (used to observe) were also Wistar rats (60-90 days, 270 g); add. of testosteron(5 mg/rat);saline control

Further Details (Pharmacological Data)

determination of mount-(the male places his forepaws on the female without pelvic movements) and thrusting-frequency ( the male places his forepaws on the female, performing repeated deep pelvic thrusting)

Results

title comp. increased the frequency of thrusting behavior after testosteron therapy, but without testosterone title comp. produced no change; title comp. did not induce mounting without testosterone therapy

160 of 174

161 of 174

162 of 174

Reference

Padoin; Lucion

European Journal of Pharmacology, 1995 , vol. 277, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.5 mg/kg

Kind of Dosing (Pharmacological Data)

in 0.9 percent saline 30 min before behavioral recording

Method (Pharmacological Data)

16 adult rats (180 d old, 320-420 g); sexual behavior was recorded 1-2 h after the begining of the dark phase by videotape; receptive females (used to observe) were also Wistar rats (60-90 day old, 270 g); saline control

Further Details (Pharmacological Data)

Results

title comp. increased the number of mounts, but had no effect on thrusting.

Reference

Padoin; Lucion

European Journal of Pharmacology, 1995 , vol. 277, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar albino rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

1 mg/kg

Method (Pharmacological Data)

rats (200-220 g) housed in colony room with 12 h light-dark cycle; learned helplessness (LH) was produced by electric shock, 40 min; experiment with non-learned helplessness (NLH) and naive rats

Further Details (Pharmacological Data)

frequency of head shake responses was quatified for 30 min before and after uncontrollable shock; corticosterone level measured 11 d after shock in basal serum

Results

before shock there is no difference between LH and NLH rats, but 11 days after the shock, responses induced by title comp. in LH rats are more frequent than in NLH or naive rats; basal corticosterone level higher in LH rats than in NLH rats

Reference

Nankai; Yamada; Muneoka; Toru

European Journal of Pharmacology, 1995 , vol. 281, # 2 p. 123 - 130 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

prefrontal cortex of Wistar albino rat

Sex

male

Route of Application

subcutaneous

Concentration

1 mg/kg

(Pharmacological Data)

163 of 174

164 of 174

Method (Pharmacological Data)

rats (200-220 g) housed in colony room with 12 h light-dark cycle; learned helplessness (LH) was produced by electric shock, 40 min; experiment with non-learned helplessness (NLH) and naive rats

Further Details (Pharmacological Data)

frequency of head shake responses was quatified for 30 min before and after uncontrollable shock; 13 d after shock rats decapitated, prefrontal cortex dissected; <3H>ketanserin binding assay

Results

there is no difference between LH and NLH rats in ketanserin binding

Reference

Nankai; Yamada; Muneoka; Toru

European Journal of Pharmacology, 1995 , vol. 281, # 2 p. 123 - 130 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

0.32 - 5 mg/kg

Kind of Dosing (Pharmacological Data)

as HCl salt

Exposure Period (Pharmacological Data)

5 - 30 min

Method (Pharmacological Data)

in vivo; 240- to 320-g rats housed in individual transparent plastic cages with food and water ad libitum until start of experiment; number of head-twitch (HTW) and/or wet dog shakes counted

Further Details (Pharmacological Data)

also in presence of var. 5-HT2A, 5-HT2C, D1, D2 and 5-HT1A antagonists

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

0.78 mg/kg

Results

dose- and time-dependently elicited HTW with max. effects at 10 (1.25-5 mg/kg) and 15 min (0.32-0.63 mg/kg) after inj.; ketanserin, ritanserin, metergoline, mesulergine, mianserin, MDL 100,907 dose dependently and completely antagonized drug-induced HTW

Reference

Schreiber; Brocco; Audinot; Gobert; Veiga; Millan

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 273, # 1 p. 101 - 112 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neuroregulatoric

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.1 - 10 mg/kg

Exposure Period (Pharmacological Data)

30 min

Method

in vivo behavioral testing; 200- to 300-g rats; also pretreated with melatonin or its agonists (15 min before drug, i.p.); head shakes

165 of 174

166 of 174

167 of 174

(Pharmacological Data)

quantified

Results

induced robust head-shake response which was reduced by melatonin or its agonists pretreatment

Reference

Eison; Freeman; Cuss; Mullins; Wright

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 273, # 1 p. 304 - 308 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

effect on substantia nigra dopamine neurons

Species or TestSystem (Pharmacological Data)

Sprague-Dawley albino rat

Sex

male

Route of Application

intravenous

Concentration (Pharmacological Data)

0.5 - 8 mg/kg

Method (Pharmacological Data)

chloral hydrate-anesthetized rats weighing 100 to 350 g; single unit recording techniques

Further Details (Pharmacological Data)

firing rate histogram

Comment (Pharmacological Data)

No effect

Reference

Shi Wei-Xing; Nathaniel; Bunney

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 2 p. 735 - 740 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat cerebellar granule cells

Method (Pharmacological Data)

pretreatment with 20 μM title comp., cells labeled with <3H>inositol phosphates, 37 deg C in saline, 5 mM LiCl; measurement of <3H>arachidonic acid release

Further Details (Pharmacological Data)

effect on phospholipase A2 (PLA2) activity

Comment (Pharmacological Data)

No effect

Reference

Chen; Li; Chuang

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 2 p. 674 - 680 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat cerebellar granule cells

Method (Pharmacological Data)

KRB buffer, 10 μM title comp. for 16 h

Further Details (Pharmacological Data)

5-HT2A/5-HT2C agonist; effects on <3H>ketanserin binding to 5-HT2A receptors

Results

specific binding : 228 percent of control

168 of 174

169 of 174

170 of 174

Reference

Chen; Li; Chuang

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 2 p. 674 - 680 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anxiolytic

Species or TestSystem (Pharmacological Data)

NMRI mice

Sex

male

Route of Application

peroral

Concentration (Pharmacological Data)

0.3 - 3 mg/kg

Method (Pharmacological Data)

mice weight 12-14 g; housed 10 per cage; stress-induced hyperthermia (higher rectal temperature of mice removed last from the cage than that of mice removed first); dose time-test interval: 60 min

Further Details (Pharmacological Data)

ΔT = basal temperature of first removed mouse minus end temperature (mouse number 10); untreated control

Results

enhanced basal T; no effect on end T; reduced ΔT

Reference

Zethof, Theo J. J.; Van der Heyden, Jan A. M.; Tolboom, Jeroen T. B. M.; Olivier, Berend

European Journal of Pharmacology, 1995 , vol. 294, # 1 p. 125 - 136 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

1 mg/kg

Kind of Dosing (Pharmacological Data)

title comp. dissolved in physiological saline; administered 10 min after raclopride and 5 min after SCH 23390; injection volume 2 ml/kg

Method (Pharmacological Data)

adult rats 250-300 g; catalepsy scored according to the time of immobility of rat placed on inclined (60 deg) grid; catalepsy induced by raclopride tartrate (16 mg/kg s.c.) or SCH 23390*HCl (0.2 mg/kg s.c.) given 30 and 20 min before testing, resp.

Results

title comp. fully antagonized catalepsy produced by raclopride; no effect on SCH 23390-produced catalepsy (diagram)

Reference

Wadenberg; Ahlenius

European Journal of Pharmacology, 1995 , vol. 294, # 1 p. 247 - 251 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

NIH 3T3 cells

Concentration (Pharmacological Data)

10 - 100000 nmol/l

Method (Pharmacological Data)

clonal cell line, stably expressed 5-hydroxytryptamine2A (5-HT2A) receptor; phosphoinositide hydrolysis rate; Western blot analysis

Type (Pharmacological

half-maximal effective conc.

Data)

171 of 174

172 of 174

173 of 174

174 of 174

Value of Type (Pharmacological Data)

20 nmol/l

Results

2-24 h exposure to title comp. diminished 5-HT2A receptor-mediated phosphoinositide hydrolysis; no change in 5-HT2A receptor number or affinity measured after 24 h

Reference

Roth; Palvimaki; Berry; Khan; Sachs; Uluer; Choudhary

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 275, # 3 p. 1638 - 1646 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hippocampal membranes

Sex

male

Concentration (Pharmacological Data)

1E-09 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

as hydrochloride

Method (Pharmacological Data)

in vitro; effect on high-affinity GTPase activity assayed by measuring amount of 32Pi released from <γ-32P>GTP; <γ-32P>GTP (spec. act.: 30 Ci/mmol); assay mixture (pH 7.4); 30 deg C; incubation time 15 min

Comment (Pharmacological Data)

No effect

Reference

Odagaki; Fuxe

European Journal of Pharmacology - Molecular Pharmacology Section, 1995 , vol. 288, # 3 p. 385 - 388 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

estimates of the Vmax and Kaff for the percent of maximum stimulation of phosphotidylinositol turnover at cloned 5-HT2A and 5-HT2C receptors

Reference

Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4346 - 4351 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

drug discrimination data, ED50: 0.97 μmol/kg; effect on the percent maximum accumulation of <3H>inositol monophosphate in 3T3 and A9 cells expressing 5-HT2Areceptors

Reference

Nichols, David E.; Frescas, Stewart; Marona-Lewicka, Danuta; Huang, Xuemei; Roth, Bryan L.; et al.

Journal of Medicinal Chemistry, 1994 , vol. 37, # 25 p. 4346 - 4351 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data) Reference

5-HT2 serotonin antagonist activity

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon

Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details

Ecotoxicology (2) 1 of 2

Effect (Ecotoxicology)

membrane current; induction of

Species or TestSystem (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-09 - 1E-06 mol/l

Kind of Dosing (Ecotoxicology)

used as hydrochloride; 6 - 7 concentrations were applied

Method (Ecotoxicology)

oocytes expressing rat 5-HT2A receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of title comp. for 10 s; stimulation of membrane currents was determined

Further Details (Ecotoxicology)

2 of 2

5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

57 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 46 percent (figure, table)

Reference

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

membrane current; induction of

Species or TestSystem (Ecotoxicology)

Xenopus laevis oocyte

Concentration (Ecotoxicology)

Ca. 1E-09 - 1E-06 mol/l

Kind of Dosing (Ecotoxicology)

used as hydrochloride; 6 - 7 concentrations were applied

Method (Ecotoxicology)

oocytes expressing rat 5-HT2C receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of title comp. for 10 s; stimulation of membrane currents was determined

Further Details (Ecotoxicology)

5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

177.8 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 90 percent (figure, table)

Reference

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

Other Data Use (15) Use Pattern

Reference

5-HT(2c) receptor modulator

AUSPEX PHARMACEUTICALS, INC.

Patent: US2008/280991 A1, 2008 ; Title/Abstract Full Text Show Details

5-HT2A/2B/2C receptor agonist; androgen binding site stimulator

Takeda Pharmaceutical Company Limited

Patent: EP1792629 A1, 2007 ; Title/Abstract Full Text Show Details

Stress urinary incontinence

Takeda Pharmaceutical Company Limited

Patent: EP1792629 A1, 2007 ; Title/Abstract Full Text Show Details

Abdominal pressure incontinence

Takeda Pharmaceutical Company Limited

Patent: EP1792629 A1, 2007 ; Title/Abstract Full Text Show Details

5HT receptors inhibition

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ; Title/Abstract Full Text Show Details

Irritable bowel syndrome

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ; Title/Abstract Full Text Show Details

Hypertrophic pyloric stenosis

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ; Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Intestinal pseudoobstruction

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

gastroparesis

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Diabetic gastroparesis

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Diabetic gastroenteropathy

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Constipation

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Hirschsprung's disease

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Functional dyspepsia

Title/Abstract Full Text Show Details

MAYO FOUNDATION FOR MEDICAL EDUCATION AND RESEARCH

Patent: WO2005/107473 A2, 2005 ;

Digestive tract conditions

Title/Abstract Full Text Show Details

Chemical Name: (+)-DOI Reaxys Registry Number: 6058828

CAS Registry Number: 99665-04-0 Type of Substance: isocyclic Molecular Formula: C11H16INO2

Linear Structure Formula: C11H16INO2

Molecular Weight: 321.158

InChI Key: BGMZUEKZENQUJY-ZETCQYMHSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-DOI, (S)-(+)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane Identification Substance Label (1) Label

Reference

(S)-1c

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

1 prep out of 1 reactions.

Identification Bioactivity (13)

Derivative (2) Derivative

Comment (Derivative)

Reference

By formation of salt/complex with (L)-(+)tartaric acid. Melting point at: 167 C - 168 C. Additional data: <α>25 deg CD 15.8 deg (water)

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

(+)-DOI hydrochloride

Purification (1) Purification (method)

Reference

via salt with (L)-(+)-tartaric acid

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (13) 1 of 13

2 of 13