1-(4-Bromo-2,5-dimethoxyphenyl)propan-2-amine [DOB] by Asch

Reaxys

PubChem

eMolecules

Reactions (35)

Substances (13)

Structure

Citations (114)

Structure/Compound Data Chemical Name: 4-bromo-2,5-dimethoxyphenylisopropylamine Reaxys Registry Number: 2807278

CAS Registry Number: 64638-07-9 Type of Substance: isocyclic Molecular Formula: C11H16BrNO2

Linear Structure Formula: C11H16BrNO2

Molecular Weight: 274.158

InChI Key: FXMWUTGUCAKGQL-UHFFFAOYSA-N

N° of preparations All Preps | All Reactions 7 prep out of 21 reactions.

Available Data

N° of ref.

Identification Physical Data (4) Spectra (4) Bioactivity (44)

Synthesize | Hide Details Find similar Chemical Names and Synonyms 4-bromo-2,5-dimethoxyphenylisopropylamine, Brolamfetamine, DOB, 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane, 2,5-dimethoxy-4bromoamphetamine, 4-bromo-2,5-dimethoxyamphetamine, 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane Identification Substance Label (7) Label

Reference

ALS MOUNTAIN LLC; CHEN, Chien-hung

Patent: WO2014/144130 A2, 2014 ; Title/Abstract Full Text Show Details

DOB

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 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

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

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

Ewald, Andreas H.; Fritschi, Giselher; Bork, Wolf-Rainer; Maurer, Hans H.

Journal of Mass Spectrometry, 2006 , vol. 41, # 4 p. 487 - 498 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

7; DOB

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

4b, DOB

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

1a, DOB

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon

Journal of Medicinal Chemistry, 2000 , vol. 43, # 16 p. 3074 - 3084 Title/Abstract Full Text View citing articles Show Details

1b, DOB

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

(+/-)DOB

Callahan; Cunningham

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 3 p. 1414 - 1424 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (3) Prophetic Compound

Related Markush Structure (RN)

prophetic product

Location in Patent

Reference

Paragraph 0040

ALS MOUNTAIN LLC; CHEN, Chien-hung

Patent: WO2014/144130 A2, 2014 ; Title/Abstract Full Text Show Details

prophetic product

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

Patent: US2007/27208 A1, 2007 ;

11337200

Title/Abstract Full Text Show Details

Claim

Tam, Peter; Gesundheit, Neil; Wilson, Leland F.

Patent: US2002/161016 A1, 2002 ; Title/Abstract Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

*HCl: F: 197-198grad; IR sp.

Bailey; Gagne; Pike

Journal - Association of Official Analytical Chemists, 1976 , vol. 59, # 5 p. 1162 - 1169 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Comment (Melting Point)

Reference

63 - 65 °C

Method: distilled sample

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

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

Liquid/Liquid Systems (MCS) (1) Description (Liquid/Liquid Systems (MCS))

Reference

Distribution between solvent 1 + 2

Barfknecht et al.

Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details

Spectra IR Spectroscopy (1) Description (IR Spectroscopy)

Reference

Spectrum

Bailey; Gagne; Pike

Journal - Association of Official Analytical Chemists, 1976 , vol. 59, # 5 p. 1162 - 1169 Title/Abstract Full Text View citing articles Show Details

UV/VIS Spectroscopy (1) Description (UV/VIS Spectroscopy)

Reference

UV/VIS

Bailey; Gagne; Pike

Journal - Association of Official Analytical Chemists, 1976 , vol. 59, # 5 p. 1162 - 1169 Title/Abstract Full Text View citing articles Show Details

Fluorescence Spectroscopy (1) Description (Fluorescence Spectroscopy)

Reference

Fluorescence

Smythies et al.

Experientia, 1971 , vol. 27, p. 62,63 Full Text Show Details

Other Spectroscopic Methods (1) Description (Other Spectroscopic Methods)

Reference

Photoelectron spectrum

Domelsmith, L. N.; Eaton, Thomas A.; Houk, K. N.; Anderson, G. M.; Glennon, R. A.; et al.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1414 - 1421 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (42) 1 of 42

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

Barfknecht; Nichols

Journal of medicinal chemistry, 1971 , vol. 14, # 4 p. 370 - 372 Title/Abstract Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Glennon; Liebowitz; Mack

Journal of Medicinal Chemistry, 1978 , vol. 21, # 8 p. 822 - 825 Title/Abstract Full Text View citing articles Show Details

Tam, Peter; Gesundheit, Neil; Wilson, Leland F.

Patent: US2002/161016 A1, 2002 ; Title/Abstract Full Text Show Details

Olney, John W.; Farber, Nuri B.

Patent: US6391871 B1, 2002 ; 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

Barfknecht et al.

Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details

Bailey; Gagne; Pike

Journal - Association of Official Analytical Chemists, 1976 , vol. 59, # 5 p. 1162 - 1169 Title/Abstract Full Text View citing articles Show Details

Smythies et al.

Experientia, 1971 , vol. 27, p. 62,63 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

Nichols; Snyder; Oberlender; Johnson; Huang

Journal of Medicinal Chemistry, 1991 , vol. 34, # 1 p. 276 - 281 Title/Abstract Full Text View citing articles Show Details

Gerdes, John M.; Mathis, Chester A.; Shulgin, Alexander T.

Tetrahedron Letters, 1988 , vol. 29, # 50 p. 6537 - 6540 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

Domelsmith, L. N.; Eaton, Thomas A.; Houk, K. N.; Anderson, G. M.; Glennon, R. A.; et al.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1414 - 1421 Title/Abstract Full Text View citing articles Show Details

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Glennon; Liebowitz; Anderson III

Journal of Medicinal Chemistry, 1980 , vol. 23, # 3 p. 294 - 299 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; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 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

2 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Glennon; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis

Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 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

Monte, Aaron P.; Marona-Lewicka, Danuta; Parker, Matthew A.; Wainscott, David B.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1996 , vol. 39, # 15 p. 2953 - 2961 Title/Abstract Full Text View citing articles Show Details

Solbach, M.; Guendisch, D.; Wuellner, U.; Blocher, A.; Kovar, K.-A.; Machulla, H.-J.

Journal of Labelled Compounds and Radiopharmaceuticals, 1997 , vol. 40, p. 522 - 524 Title/Abstract Full Text 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

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 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

Callahan; Cunningham

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 3 p. 1414 - 1424 Title/Abstract Full Text View citing articles Show Details

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon

Journal of Medicinal Chemistry, 2000 , vol. 43, # 16 p. 3074 - 3084 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

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

Rangisetty; Dukat; Dowd; Herrick-Davis; DuPre; Gadepalli; Teitler; Kelley; Sharif; Glennon

Journal of Medicinal Chemistry, 2001 , vol. 44, # 20 p. 3283 - 3291 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

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 304, # 1 p. 229 - 237 Title/Abstract Full Text View citing articles Show Details

Peddi, Srinivas; Roth, Bryan L.; Glennon, Richard A.; Westkaemper, Richard B.

Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 15 p. 2565 - 2568 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

Chambers, James J.; Parrish, Jason C.; Jensen, Niels H.; Kurrasch-Orbaugh, Deborah M.; Marona-Lewicka, Danuta; Nichols, David E.

Journal of Medicinal Chemistry, 2003 , vol. 46, # 16 p. 3526 - 3535 Title/Abstract Full Text View citing articles Show Details

Altun, Ahmet; Golcuk, Kurtulus; Kumru, Mustafa; Jalbout, Abraham F.

Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 18 p. 3861 - 3868 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

Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 10 p. 2545 - 2552 Title/Abstract Full Text View citing articles Show Details

3 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

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

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

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

Ewald, Andreas H.; Fritschi, Giselher; Bork, Wolf-Rainer; Maurer, Hans H.

Journal of Mass Spectrometry, 2006 , vol. 41, # 4 p. 487 - 498 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

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

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

Schultz, Danielle M.; Prescher, Jennifer A.; Kidd, Stephanie; Marona-Lewicka, Danuta; Nichols, David E.; Monte, Aaron

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 11 p. 6242 - 6251 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

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

Thomsen, William J; Grottick, Andrew J; Menzaghi, Frederique; Reyes-Saldana, Hazel; Espitia, Stephen; Yuskin, Diane; Whelan, Kevin; Martin, Michael; Morgan, Michael; Chen, Weichao; Al-Shamma, Hussien; Smith, Brian; Chalmers, Derek; Behan, Dominic

The Journal of pharmacology and experimental therapeutics, 2008 , vol. 325, # 2 p. 577 - 587 Title/Abstract Full Text 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

Barfknecht; Nichols; Dunn III

Journal of Medicinal Chemistry, 1975 , vol. 18, # 2 p. 208 - 210 Title/Abstract Full Text Show Details

Aldous; Barrass; Brewster; Buxton; Green; Pinder; Rich; Skeels; Tutt

Journal of Medicinal Chemistry, 1974 , vol. 17, # 10 p. 1100 - 1111

Title/Abstract Full Text Show Details

Kier; Hall

Journal of Medicinal Chemistry, 1977 , vol. 20, # 12 p. 1631 - 1636 Title/Abstract Full Text Show Details

Whiteside, Michael S; Kurrasch-Orbaugh, Deborah; Marona-Lewicka, Danuta; Nichols, David E; Monte, Aaron

Bioorganic and medicinal chemistry, 2002 , vol. 10, # 10 p. 3301 - 3306 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

Teitler, Milt; Herrick-Davis, Katharine; Purohit, Anil

Current topics in medicinal chemistry, 2002 , vol. 2, # 6 p. 529 - 538 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A; Metwally, Kamel; Dukat, Malgorzata; Ismaiel, Abd M; De los Angeles, Joseph; Herndon, Jeffery; Teitler, Milt; Khorana, Nantaka

Current topics in medicinal chemistry, 2002 , vol. 2, # 6 p. 539 - 558 Title/Abstract Full Text View citing articles Show Details

4 of 42

5 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

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

Herrick-Davis, Katharine; Egan, Christina; Teitler, Milt

Journal of Neurochemistry, 1997 , vol. 69, # 3 p. 1138 - 1144 Title/Abstract Full Text View citing articles Show Details

Sleight; Stam; Mutel; Vanderheyden

Biochemical Pharmacology, 1996 , vol. 51, # 1 p. 71 - 76 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

Leonhardt; Gorospe; Hoffman; Teitler

Molecular Pharmacology, 1992 , vol. 42, # 2 p. 328 - 335 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

Leonhardt; Herrick-Davis; Titeler

Journal of Neurochemistry, 1989 , vol. 53, # 2 p. 465 - 471 Title/Abstract Full Text View citing articles Show Details

Herrick-Davis; Titeler; Leonhardt; Struble; Price

Journal of neurochemistry, 1988 , vol. 51, # 6 p. 1906 - 1912 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

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

Herrick-Davis; Titeler

Journal of Neurochemistry, 1988 , vol. 50, # 5 p. 1624 - 1631 Title/Abstract Full Text View citing articles Show Details

Gomez-Jeria; Cassels; Saavedra-Aguilar

European Journal of Medicinal Chemistry, 1987 , vol. 22, # 5 p. 433 - 437 Title/Abstract Full Text Show Details

Titeler; Lyon; Davis; Glennon

Biochemical Pharmacology, 1987 , vol. 36, # 19 p. 3265 - 3271 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

Lyon; Davis; Titeler

Molecular pharmacology, 1987 , vol. 31, # 2 p. 194 - 199 Title/Abstract Full Text Show Details

Glennon; McKenney; Lyon; Titeler

Journal of medicinal chemistry, 1986 , vol. 29, # 2 p. 194 - 199 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

Domelsmith; Eaton; Houk; Anderson III; Glennon; Shulgin; Castagnoli Jr.; Kollman

Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1414 - 1421 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

S.P.Gupta

Chemical reviews, 1989 , vol. 89, # 8 p. 1765 - 1800 Title/Abstract Full Text Show Details

Comment (Pharmacological

Bioactivities present

Data) Reference

SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL

Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text Show Details

ALS MOUNTAIN LLC; CHEN, Chien-hung

Patent: WO2014/144130 A2, 2014 ; Title/Abstract Full Text Show Details

Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan

Patent: EP2950104 A1, 2015 ; Title/Abstract Full Text 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

Rojek, Sebastian; Bolechała, Filip; Kula, Karol; Maciów-Głąb, Martyna; Kłys, Małgorzata

Legal Medicine, 2016 , vol. 21, p. 64 - 72 Title/Abstract Full Text View citing articles Show Details

Rychert, Marta; Wilkins, Chris

Drug Testing and Analysis, 2016 , vol. 8, # 8 p. 768 - 778 Title/Abstract Full Text View citing articles Show Details

Rojek, Sebastian; Kula, Karol; Maciów-Głąb, Martyna; Kłys, Małgorzata

Forensic Toxicology, 2016 , vol. 34, # 2 p. 403 - 410 Title/Abstract Full Text View citing articles 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

Saz; Marina

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

Bumbrah, Gurvinder Singh; Sharma, Rakesh Mohan

Egyptian Journal of Forensic Sciences, 2016 , vol. 6, # 3 p. 209 - 215 Title/Abstract Full Text Show Details

Souza, Luciano F.; Vieira, Tarcísio S.; Alcantara, Glaucia B.; Lião, Luciano M.

Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 11 p. 2141 - 2148 Title/Abstract Full Text Show Details

6 of 42

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan

Patent: EP2950104 A1, 2015 ; Title/Abstract Full Text Show Details

7 of 42

8 of 42

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)

[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)

41 nmol/l

9 of 42

10 of 42

11 of 42

12 of 42

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

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 (Pharmacological Data)

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

Further Details (Pharmacological Data)

control: saline; 5-HT: serotonin

Results

title comp. induced robust head shake behavior in comparison with control (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)

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 PLC-mediated IP accumulation (RE = ca. 40percent, pEC50 = 6.18); RE for PLA2-mediated AA release was ca. 30percent, pEC50 = 6.14 (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)

agonist

Species or Test-

CHO-1C19 cells expressing human 5-HT2C receptors

System (Pharmacological Data)

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Method (Pharmacological Data)

Further Details (Pharmacological Data)

Results

title comp. preferentially stimulated PLA2-mediated AA release (RE = ca. 60percent) and pEC50 = 7.18; RE for PLC-mediated IP response was ca. 40percent, pEC50 = 7.32 (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)

biotransformation

Species or TestSystem (Pharmacological Data)

rat

Route of Application

peroral

Concentration (Pharmacological Data)

5 mg/kg

Method (Pharmacological Data)

in vivo; urine collected separately from feces for 24 h; samples analyzed by GC/MS

Metabolite (Pharmacological Data)

2-(acetylamino)-1-(4-bromo-2,5-dimethoxyphenyl)propyl acetate [Reaxys RN: 10357380] ; 1-(4-bromo-2,5-dimethoxyphenyl)acetone [Reaxys RN: 10340917] ; 2-(4-bromo-2,5-dimethoxyphenyl)-1-methylethyl acetate [Reaxys RN: 10346948]

Comment (Pharmacological Data)

Further metabolite(s)

Reference

Ewald, Andreas H.; Fritschi, Giselher; Bork, Wolf-Rainer; Maurer, Hans H.

Journal of Mass Spectrometry, 2006 , vol. 41, # 4 p. 487 - 498 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)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 0.1 nmol/l <125I>-DOI used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 5 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharmacological Data)

nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); DOI: 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane; title comp. binding affinity to recombinant 5-HT2A receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

8.93 dimensionless

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

receptor; binding activity

Data)

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17 of 42

Species or TestSystem (Pharmacological Data)

CHO-K1 cell membranes expressing human 5-HT2B receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 5 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer supplemented with 4 mmol/l CaCl2; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharmacological Data)

nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding affinity to recombinant 5-HT2B receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

7.36 dimensionless

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-HT2C receptor

Concentration (Pharmacological Data)

1E-11 - 1E-06 mol/l

Method (Pharmacological Data)

competition binding assay; 1 nmol/l <3H>-5-HT used as radioligand; membranes incubated with radioligand and title comp. for 1 h at 37 deg C in assay buffer; radioactivity quantified by Packard Topcount plate reader

Further Details (Pharmacological Data)

nonspecific binding defined with 10 μmol/l 5-HT (5-hydroxytryptamine); title comp. binding affinity to recombinant 5-HT2C receptor subtype studied; assay buffer: Tris-HCl containing 0.1 percent ascorbate

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

8.20 dimensionless

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)

agonist

Endpoint of Effect (Pharmacological Data)

arachidonic acid (AA) release

Species or TestSystem (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

0.0001 - 10 μmol/l

Method (Pharmacological Data)

cells labeled with <3H>AA for 4 h; washed three times with DMEM and incubated with title comp. for 30 min at 37 deg C; <3H>AA in medium counted

Further Details (Pharmacological Data)

5-HT = 5-hydroxytryptamine; DMEM = Dulbecco's modified Eagle's medium; control: without title comp.

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Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

15 nmol/l

Results

title comp. stimulated the <3H>AA accumulation conc.-dependently (table)

Reference

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 304, # 1 p. 229 - 237 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Endpoint of Effect (Pharmacological Data)

IPs accumulation

Species or TestSystem (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

0.001 - 10 μmol/l

Method (Pharmacological Data)

cells loaded with myo-<2-3H(N)>inositol and pretreated with 10 μmol/l pargyline and 10 mmol/l LiCl for 15 min at 37 deg C in CMRL-1066 media; then title comp. added for 30 min; <3H>IPs of cell lysate separated by ion-exchange chromatography and counted

Further Details (Pharmacological Data)

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5-HT = 5-hydroxytryptamine; IPs = a mixture of inositol mono- bis-, and triphosphate; control: without title comp.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

72 nmol/l

Results

title comp. stimulated the <3H>IPs accumulation conc.-dependently (table)

Reference

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 304, # 1 p. 229 - 237 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Endpoint of Effect (Pharmacological Data)

<125I>2,5-dimethoxy-4-iodoamphetamine (DOI) binding

Species or TestSystem (Pharmacological Data)

NIH3T3 fibroblasts stably expressing 5-HT2A receptors

Concentration (Pharmacological Data)

1E-05 - 10 μmol/l

Method (Pharmacological Data)

competition binding study; cells incubated with 2E-1 nmol/l <125I>DOI in the presence title comp. for 60 min at 25 deg C in Tris-EDTA buffer, pH 7.4; nonspecific binding determ. with 10 μmol/l cinanserin; filter-bound radioactivity counted

Further Details (Pharmacological Data)

5-HT = 5-hydroxytryptamine; control: without title comp.

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4.3 nmol/l

Reference

Kurrasch-Orbaugh, Deborah M.; Watts, Val J.; Barker, Eric L.; Nichols, David E.

Journal of Pharmacology and Experimental Therapeutics, 2003 , vol. 304, # 1 p. 229 - 237

Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

NIH-3T3 fibroblasts expressing rat 5-HT2A receptors

Method (Pharmacological Data)

in vitro; competition binding assay; <3H>DOB used as radioligand; Tris buffer, pH 7.4; 25 deg C; 60 min; scintillation counting; nonspecific binding determined in the presence of 10 μM cinanserin

Further Details (Pharmacological Data)

DOB: 4-bromo-2,5-dimethoxyamphetamine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.2 nmol/l

Reference

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

NIH-3T3 fibroblasts expressing rat 5-HT2C receptors

Method (Pharmacological Data)

in vitro; competition binding assay; <125I>DOI used as radioligand; Tris buffer, pH 7.4; 25 deg C; 60 min; scintillation counting; nonspecific binding determined in the presence of 10 μM mianserin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

2.8 nmol/l

Reference

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

NIH-3T3 fibroblasts expressing rat 5-HT2A receptors

Method (Pharmacological Data)

in vitro; phosphoinositol hydrolysis study; cells labeled for 18-20 h in CRML medium containing <3H>myo-inositol; after pretreating cells with 10 μM pargyline for 15 min, cells were incubated with title comp. at 37 deg C for 30 min

Further Details (Pharmacological Data)

95percent O2/5percent CO2 atmosphere; <3H>inositol phosphates separated by LC and quantified by scintillation counting

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

72 nmol/l

Results

percent max. 5-HT stimulation: 79percent

Reference

Chambers; Kurrasch-Orbaugh; Parker; Nichols

Journal of Medicinal Chemistry, 2001 , vol. 44, # 6 p. 1003 - 1010 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

NIH-3T3 cell membranes expressing rat 5-HT2A receptors

Kind of Dosing (Pharmacological Data)

as hydrochloride

Method (Pharmacological Data)

in vitro; radioligand competition binding assay; 0.5 nmol/l <3H>ketanserin used as radioligand; binding buffer, pH 7.4; 37 deg C; incubated for 30 min; liquid scintillation counting; nonspecific binding determined using 10 μmol/l ketanserin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

32 nmol/l

Reference

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon

Journal of Medicinal Chemistry, 2000 , vol. 43, # 16 p. 3074 - 3084 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

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A-9 cell membranes expressing rat 5-HT2C receptors

Kind of Dosing (Pharmacological Data)

as hydrochloride salt

Method (Pharmacological Data)

in vitro; radioligand competition binding assay; 2.0 nmol/l <3H>mesulegrine used as radioligand; binding buffer, pH 7.4; 37 deg C; incubated for 30 min; liquid scintillation counting; nonspecific binding determined using 1 μmol/l mesulegrine

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

64 nmol/l

Reference

Dowd; Herrick-Davis; Egan; DuPre; Smith; Teitler; Glennon

Journal of Medicinal Chemistry, 2000 , vol. 43, # 16 p. 3074 - 3084 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 Data)

0.01 - 100 μmol/l

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

No effect

Data)

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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)

100 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

Comment (Pharmacological Data)

in vivo drug discrimination: ED50 = 1.12 mmol/kg in LSD-trained male Sprague-Dawley rats; in vitro affinity at <3H>ketanserin-labeled rat cortical 5-HT2A and <3H>-8-OH-DPAT-labeled rat hippocampal 5-HT1A receptors (male Sprague-Dawley rat)

Reference

Monte, Aaron P.; Marona-Lewicka, Danuta; Parker, Matthew A.; Wainscott, David B.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1996 , vol. 39, # 15 p. 2953 - 2961 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

hallucinogenic

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mg/kg

Method (Pharmacological Data)

15 min before testing animals treated with 1.0 mg/kg of (+/-)-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane hydrochloride (DOM) i.p. injection, as training drug; data collected during 2.5 min extinction session

Results

produced 91 percent drug-appropriate responding

Reference

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-

NIH 3T3 cell membranes expressing human 5HT

receptors

System (Pharmacological Data)

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Concentration (Pharmacological Data)

0.05 - 15 nmol/l

Method (Pharmacological Data)

in vitro; saturation binding assay; <3H>labeled title comp. (spec. act.: 16 Ci/mmol); assay buffer (pH 7.4); room temp.; incubation time 1 h; scintillation spectroscopy

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.8 nmol/l

Results

Bmax: 8332 fmol/mg protein; graphical representation

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

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)

610 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)

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 (Pharmacological Data)

22 nmol/l

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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 test; specific uptake defined in absence of test cmpd; 37 deg C; liquid scintillation analysis

Further Details (Pharmacological Data)

inhibition of <3H> dopamine and of <3H> norepinephrine uptake

Results

no significant effect up to 100 and 50 μM resp.

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)

14 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)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

rat

Method (Pharmacological Data)

in vivo; two-lever drug discrimination test in rats trained to discriminate LSD from saline; 4 - 6 dose levels; 8 - 12 rats tested at each dose

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

1.12 μmol/kg

Results

test compd fully substituted LSD

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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)

agonist

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Concentration (Pharmacological Data)

0.0625 - 0.5 mg/kg

Method (Pharmacological Data)

300-350 g, 60 days old animals, training to discriminate 10 mg/kg cocaine

Further Details (Pharmacological Data)

5-HT2A/2C receptor agonist; cocaine-substitution test; modulation of the discriminative stimulus properties of cocaine

Results

30-70 percent of cocaine-appropriate responding; 0.125-0.5 mg/kg title comp. did not block the stimulus of cocaine

Reference

Callahan; Cunningham

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 3 p. 1414 - 1424 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: 1.12 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)

binding affinity at 5-HT1C serotonin receptor

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

Comment (Pharmacological Data) Reference

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Comment (Pharmacological Data)

ability to displace<125I>-(R)-DOI (<125I>-(R)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane) from rat cortical homogenate 5-HT2

receptors

Nichols; Snyder; Oberlender; Johnson; Huang

Journal of Medicinal Chemistry, 1991 , vol. 34, # 1 p. 276 - 281 Title/Abstract Full Text View citing articles Show Details

5-HT2 serotonin antagonist activity

Reference

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

Comment (Pharmacological Data)

serotonin binding affinity in the rat stomach fundus

Reference

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological

affinity for 5-HT2 binding sites

Data) Reference

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 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

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 increasing concentrations 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)

50 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 57 percent (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

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 increasing concentrations 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)

101.7 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 58 percent (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

Chemical Name: (+)-Brolamfetamine Reaxys Registry Number: 3032545

CAS Registry Number: 43061-16-1 Type of Substance: isocyclic Molecular Formula: C11H16BrNO2

Linear Structure Formula: C11H16BrNO2

Molecular Weight: 274.158

InChI Key: FXMWUTGUCAKGQL-ZETCQYMHSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms

5 prep out of 6 reactions.

Identification Bioactivity (8)

(+)-Brolamfetamine, (S)-4-bromo-2,5-dimethoxyamphetamine, (+)-4-Brom-2,5-dimethoxyphenylisopropylamin, (S)-(+)-1-(4-bromo-2,5dimethoxyphenyl)-2-aminopropane Identification Substance Label (3) Label

Reference

(S)-(+)-DOB

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Derivative (1) Comment (Derivative)

Reference

Hydrochlorid: F: 204-205grad; <α>(D)25: +13.7grad

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Bioactivity Pharmacological Data (8) 1 of 8

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 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

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 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

Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt

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

McKenna; Peroutka

The Journal of neuroscience : the official journal of the Society for Neuroscience, 1989 , vol. 9, # 10 p. 3482 - 3490 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

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

Gomez-Jeria; Cassels; Saavedra-Aguilar

European Journal of Medicinal Chemistry, 1987 , vol. 22, # 5 p. 433 - 437 Title/Abstract Full Text Show Details

Rasmussen; Glennon; Aghajanian

European Journal of Pharmacology, 1986 , vol. 132, # 1 p. 79 - 82

Title/Abstract Full Text Show Details

Lyon; Davis; Titeler

Molecular pharmacology, 1987 , vol. 31, # 2 p. 194 - 199 Title/Abstract Full Text Show Details

2 of 8

3 of 8

4 of 8

5 of 8

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant human TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1; effective concentration (EC); EC50 related to: human TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

15.34 μmol/l

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant human TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

molecular target: human TAAR1

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1; effective concentration (EC); EC50 related to: monkey TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.14 μmol/l

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

6 of 8

7 of 8

8 of 8

Results

molecular target: monkey TAAR1

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

serotonin binding affinity in the rat stomach fundus

Reference

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

affinity for 5-HT2 binding sites

Reference

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

discrimination of intraperitoneal injections of (R)-(-)-DOB*HCl from saline in rats; ED50=0.56 (0.29-1.08) mg/kg

Reference

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (-)-Brolamfetamine

5 prep out of 5 reactions.

Reaxys Registry Number: 3032546

CAS Registry Number: 43061-15-0 Type of Substance: isocyclic Molecular Formula: C11H16BrNO2

Linear Structure Formula: C11H16BrNO2

Molecular Weight: 274.158

InChI Key: FXMWUTGUCAKGQL-SSDOTTSWSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms (-)-Brolamfetamine, (R)-4-bromo-2,5-dimethoxyamphetamine, (-)-4-Brom-2,5-dimethoxyphenylisopropylamin, (R)-(-)-1-(4-bromo-2,5dimethoxyphenyl)-2-aminopropane Identification Substance Label (3) Label

Reference

(R)-(-)-DOB

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Derivative (1) Comment (Derivative) Hydrochlorid: F: 203.5-204grad;

Reference <α>(D)25:

-13.7grad

Univ. Iowa

Identification Bioactivity (7)

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Bioactivity Pharmacological Data (7) 1 of 7

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

VIRGINIA COMMONWEALTH UNIVERSITY

Patent: WO2004/28451 A2, 2004 ; Title/Abstract Full Text Show Details

MILES INC.

Patent: WO1992/4015 A1, 1992 ; Title/Abstract Full Text Show Details

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 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

Monte, Aaron P.; Marona-Lewicka, Danuta; Lewis, Mechelle M.; Mailman, Richard B.; Wainscott, David B.; Nelson, David L.; Nichols, David E.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 12 p. 2134 - 2145 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

Hitchcock, Stephen A.; Pennington, Lewis D.

Journal of Medicinal Chemistry, 2006 , vol. 49, # 26 p. 7559 - 7583 Title/Abstract Full Text View citing articles Show Details

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 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

Deeb, Omar; Clare, Brian W.

Chemical Biology and Drug Design, 2008 , vol. 71, # 4 p. 352 - 362 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

Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt

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

Schmidt; Peroutka

Molecular Pharmacology, 1990 , vol. 38, # 4 p. 511 - 516 Title/Abstract Full Text Show Details

McKenna; Peroutka

The Journal of neuroscience : the official journal of the Society for Neuroscience, 1989 , vol. 9, # 10 p. 3482 - 3490 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

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

Rasmussen; Glennon; Aghajanian

European Journal of Pharmacology, 1986 , vol. 132, # 1 p. 79 - 82 Title/Abstract Full Text Show Details

Lyon; Davis; Titeler

Molecular pharmacology, 1987 , vol. 31, # 2 p. 194 - 199 Title/Abstract Full Text Show Details

2 of 7

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem

RD-HGA16 cells; genetically modified/infected with: recombinant human TAAR1

(Pharmacological Data)

3 of 7

4 of 7

5 of 7

6 of 7

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1; effective concentration (EC); EC50 related to: human TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

31.94 μmol/l

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant human TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

molecular target: human TAAR1

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1; effective concentration (EC); EC50 related to: monkey TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

13.9 μmol/l

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

molecular target: monkey TAAR1

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

affinity for 5-HT2 binding sites

Reference

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

7 of 7

Comment (Pharmacological Data)

discrimination of intraperitoneal injections of (R)-(-)-DOB*HCl from saline in rats; ED50=0.05 (0.03-0.09) mg/kg

Reference

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 4906241

CAS Registry Number: 32156-26-6, 43061-15-0, 43061-16-1, 6463807-9 Type of Substance: isocyclic Molecular Formula: C11H16BrNO2

Linear Structure Formula: C11H16BrNO2

Molecular Weight: 274.158

InChI Key: FXMWUTGUCAKGQL-UHFFFAOYSA-N

no reactions.

Synthesize | Hide Details Find similar

Identification Substance Label (2) Label

Reference

2-(+)

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

(+)-7

Glennon; Young; Benington; Morin

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

Bioactivity Pharmacological Data (4) 1 of 4

2 of 4

3 of 4

4 of 4

Comment (Pharmacological Data)

Bioactivities present

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 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

Comment (Pharmacological Data)

binding affinity at 5-HT1C serotonin receptor

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

Comment (Pharmacological Data)

affinity binding at 5-HT1C receptor

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

Comment (Pharmacological

the serotonin (5-HT) receptor affinities, ED50= 0.81 mg/kg; human hallucinogen

Identification Bioactivity (4)

Data) Reference

Glennon; Young; Benington; Morin

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

Reaxys Registry Number: 4906242

CAS Registry Number: 32156-26-6, 43061-15-0, 43061-16-1, 6463807-9 Type of Substance: isocyclic Molecular Formula: C11H16BrNO2

Linear Structure Formula: C11H16BrNO2

Molecular Weight: 274.158

InChI Key: FXMWUTGUCAKGQL-UHFFFAOYSA-N

no reactions.

Identification Bioactivity (3)

Identification

Synthesize | Hide Details Find similar

Identification Substance Label (2) Label

Reference

2-(-)

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

(-)-7

Glennon; Young; Benington; Morin

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

Bioactivity Pharmacological Data (3) 1 of 3

2 of 3

3 of 3

Comment (Pharmacological Data)

Bioactivities present

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 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

Comment (Pharmacological Data)

binding affinity at 5-HT1C serotonin receptor

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

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

Comment (Pharmacological Data)

the serotonin (5-HT) receptor affinities, ED50= 0.10 mg/kg; human hallucinogen

Reference

Glennon; Young; Benington; Morin

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

Chemical Name: (+/-)-1-(4-bromo-2,5-dimethoxyphenyl)-2-propaneamine-d6 Reaxys Registry Number: 11155619

Molecular Formula: C11H16BrNO2

Linear Structure Formula: C11H10(2)H6BrNO2

Molecular Weight: 280.11

1 prep out of 1 reactions.

InChI Key: FXMWUTGUCAKGQL-XERRXZQWSA-N 6

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+/-)-1-(4-bromo-2,5-dimethoxyphenyl)-2-propaneamine-d6, (+/-)-2,5-dimethoxy-4-bromoamphetamine-d6 Identification Substance Label (1) Label

Reference

Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao

Journal of the Chinese Chemical Society, 2007 , vol. 54, # 2 p. 493 - 502 Title/Abstract Full Text View citing articles Show Details

Chemical Name: Brolamfetamine hydrochloride

no reactions.

Reaxys Registry Number: 4029553

CAS Registry Number: 29705-96-2 Type of Substance: isocyclic Molecular Formula: C11H16BrNO2*ClH Linear Structure Formula: C11H16BrNO2*ClH Molecular Weight: 310.618

InChI Key: SPBBKPOIDQIWDZ-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms Brolamfetamine hydrochloride, (+/-)-DOB, (+/-)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane hydrochloride, (+/-)-1-(4-bromo-2,5dimethoxyphenyl)-2-aminopropane hydrochloride, (+/-)-2,5-dimethoxy-4-bromoamphetamine hydrochloride, 2,5-Dimethoxy-4-bromoamphetamine hydrochloride, (dl)-4-bromo-2,5-dimethoxyamphetamineHCl Identification Substance Label (4) Label

Reference

DOB

Nelson; Lucaites; Wainscott; Glennon

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels

Naunyn-Schmiedeberg's archives of pharmacology, 1996 , vol. 354, # 5 p. 579 - 585 Title/Abstract Full Text View citing articles Show Details

DOB hydrochloride

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

Coutts; Malicky

Canadian Journal of Chemistry, 1973 , vol. 51, # 9 p. 1402 - 1409

Identification Physical Data (3) Spectra (3) Bioactivity (9)

Title/Abstract 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

1e-HCl

Patent-Specific Data (1) Location in Patent

Reference

Claim

Luminis Pty Limited

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

Physical Data Melting Point (3) Melting Point

Solvent (Melting Point)

Reference

201 - 202 °C

propan-2-ol diethyl ether

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

197 - 198 °C

ethanol diethyl ether

Coutts; Malicky

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

Barfknecht; Nichols

Journal of medicinal chemistry, 1971 , vol. 14, # 4 p. 370 - 372 Title/Abstract Full Text View citing articles Show Details

198 - 199 °C

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Chemical shifts

D2O

Spin-spin coupling constants

Comment (NMR Spectroscopy)

Reference Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

D2O

1H-1H

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Reference

Bands

Coutts; Malicky

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

Bioactivity Pharmacological Data (9) 1 of 9

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

Barfknecht; Nichols

Journal of medicinal chemistry, 1971 , vol. 14, # 4 p. 370 - 372 Title/Abstract Full Text View citing articles Show Details

Glennon; Liebowitz; Mack

Journal of Medicinal Chemistry, 1978 , vol. 21, # 8 p. 822 - 825 Title/Abstract Full Text View citing articles Show Details

Luminis Pty Limited

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

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 Title/Abstract Full Text View citing articles Show Details

Nelson; Lucaites; Wainscott; Glennon

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels

Naunyn-Schmiedeberg's archives of pharmacology, 1996 , vol. 354, # 5 p. 579 - 585 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

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

Porter; Benwell; Lamb; Malcolm; Allen; Revell; Adams; Sheardown

British Journal of Pharmacology, 1999 , vol. 128, # 1 p. 13 - 20 Title/Abstract Full Text View citing articles Show Details

Reyes-Parada, Miguel; Scorza, Cecilia; Romero, Veronica; Silveira, Rodolfo; Medina, Jorge H.; Andrus, Danice; Nichols, David E.; Cassels, Bruce K.

Naunyn-Schmiedeberg's Archives of Pharmacology, 1996 , vol. 354, # 5 p. 579 - 585 Title/Abstract Full Text View citing articles Show Details

SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL

Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text Show Details

Odagaki, Yuji; Kinoshita, Masakazu; Toyoshima, Ryoichi

European Journal of Pharmacology, 2014 , vol. 726, # 1 p. 109 - 115 Title/Abstract Full Text View citing articles Show Details

2 of 9

3 of 9

4 of 9

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Odagaki, Yuji; Kinoshita, Masakazu; Toyoshima, Ryoichi

European Journal of Pharmacology, 2014 , vol. 726, # 1 p. 109 - 115 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

membrane preparation of human 5-HT2A receptors

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with human 5-HT2A receptors; receptors labeled with <125I>1-(4-iodo-2,5dimethoxyphenyl)propan-2-amine; determination of non-specific binding

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

0.6 mmol/l

Reference

Nelson; Lucaites; Wainscott; Glennon

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

membrane preparation of rat 5-HT2B receptors

5 of 9

6 of 9

7 of 9

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with rat 5-HT2B receptors; receptors labeled with <3H>serotonin; determination of nonspecific binding

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

21.8 nmol/l

Reference

Nelson; Lucaites; Wainscott; Glennon

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

membrane preparation of human 5-HT2C receptors

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with human 5-HT2C receptors; receptors labeled with <125I>1-(4-iodo-2,5dimethoxyphenyl)propan-2-amine; determination of non-specific binding

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

1.3 nmol/l

Reference

Nelson; Lucaites; Wainscott; Glennon

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

membrane preparation of human 5-HT2B receptors

Method (Pharmacological Data)

suspension-grown AV12 cells stably transformed with human 5-HT2B receptors; receptors labeled with <3H>serotonin; determination of non-specific binding

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

26.9 nmol/l

Reference

Nelson; Lucaites; Wainscott; Glennon

Naunyn-Schmiedeberg's Archives of Pharmacology, 1999 , vol. 359, # 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

Exposure Period (Pharmacological Data)

30 min

8 of 9

9 of 9

Method (Pharmacological Data)

rats 200-240 g; number of head shakes counted in response to title comp.

Results

significantly increased number of head shakes, num. table

Reference

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels

Naunyn-Schmiedeberg's archives of pharmacology, 1996 , vol. 354, # 5 p. 579 - 585 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat brain 5-HT1A receptors

Method (Pharmacological Data)

frontal cortex or hippocampal homogenates preincubated with <3H>8-OH-DPAT, then with var. conc. title comp. 15 min, 37 deg C (displacement study); scintillation counting

Further Details (Pharmacological Data)

<3H>8-OH-DPAT bound to single site, Bmax: 110 fmol/mg protein, KD 0.67 nM; specific binding defined as displaceable with 10 μM 5-HT

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

4450 nmol/l

Reference

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels

Naunyn-Schmiedeberg's archives of pharmacology, 1996 , vol. 354, # 5 p. 579 - 585 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat brain 5-HT2A/2C receptors

Method (Pharmacological Data)

frontal cortex or hippocampal homogenates preincubated with <3H>ketanserin, then with var. conc. title comp. 15 min, 37 deg C (displacement study); scintillation counting

Further Details (Pharmacological Data)

<3H>ketanserin bound to single site, Bmax: 180 fmol/mg protein, KD 0.83 nM; specific binding defined as displaceable with 10 μM cinanserin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

60 nmol/l

Reference

Reyes-Parada; Scorza; Romero; Silveira; Medina; Andrus; Nichols; Cassels

Naunyn-Schmiedeberg's archives of pharmacology, 1996 , vol. 354, # 5 p. 579 - 585 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (+)-Brolamfetamine hydrochloride Reaxys Registry Number: 7285368

Type of Substance: isocyclic Molecular Formula: C11H16BrNO2*ClH Linear Structure Formula: C11H16BrNO2*ClH Molecular Weight: 310.618

InChI Key: SPBBKPOIDQIWDZ-FJXQXJEOSA-N

Synthesize | Hide Details

no reactions.

Identification Physical Data (2) Bioactivity (1)

Find similar Chemical Names and Synonyms (+)-Brolamfetamine hydrochloride, (S)(+)-2,5-Dimethoxy-4-bromamphetamin-hydrochlorid Identification Substance Label (1) Label

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

204 - 205 °C

propan-2-ol

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Optical Rotatory Power (1) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

2 g/100ml

H2O

13.7 deg

589 nm

25 °C

Reference Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Dyer; Nichols; Rusterholz; Barfknecht

Life Sciences, 1973 , vol. 13, # 7 p. 885 - 896 Title/Abstract Full Text Show Details

Chemical Name: (-)-Brolamfetamine hydrochloride Reaxys Registry Number: 7285369

Type of Substance: isocyclic Molecular Formula: C11H16BrNO2*ClH Linear Structure Formula: C11H16BrNO2*ClH Molecular Weight: 310.618

InChI Key: SPBBKPOIDQIWDZ-OGFXRTJISA-N

Synthesize | Hide Details Find similar

no reactions.

Identification Physical Data (2) Bioactivity (1)

Chemical Names and Synonyms (-)-Brolamfetamine hydrochloride, (R)(-)-2,5-Dimethoxy-4-bromamphetamin-hydrochlorid Identification Substance Label (1) Label

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

203.5 - 204 °C

propan-2-ol

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Optical Rotatory Power (1) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

2 g/100ml

H2O

-13.7 deg

589 nm

25 °C

Reference Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Glennon; Titeler; Seggel; Lyon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 5 p. 930 - 932 Title/Abstract Full Text View citing articles Show Details

Dyer; Nichols; Rusterholz; Barfknecht

Life Sciences, 1973 , vol. 13, # 7 p. 885 - 896 Title/Abstract Full Text Show Details

Chemical Name: (+/-)-2,5-dimethoxy-4-bromoamphetamine-d6 hydrochloride Reaxys Registry Number: 11155620

Molecular Formula: C11H16BrNO2*ClH Linear Structure Formula: C11H10(2)H6BrNO2*HCl Molecular Weight: 316.571

InChI Key: SPBBKPOIDQIWDZ-HVTBMTIBSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms

no reactions.

Identification Spectra (3)

(+/-)-2,5-dimethoxy-4-bromoamphetamine-d6 hydrochloride Identification Substance Label (1) Label

Reference

6*HCl

Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao

Journal of the Chinese Chemical Society, 2007 , vol. 54, # 2 p. 493 - 502 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

CDCl3

300 MHz

Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao

Journal of the Chinese Chemical Society, 2007 , vol. 54, # 2 p. 493 - 502 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

CDCl3

75.5 MHz

Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao

Journal of the Chinese Chemical Society, 2007 , vol. 54, # 2 p. 493 - 502 Title/Abstract Full Text View citing articles Show Details

Reference

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Reference

Bands

film

Xu, Ya-Zhu; Lin, Huei-Ru; Lua, Chang-Ahai; Chen, Chinpiao

Journal of the Chinese Chemical Society, 2007 , vol. 54, # 2 p. 493 - 502 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (+/-)-1-(2,5-dimethoxy-4-bromophenyl)propan-2-amine hydrobromide Reaxys Registry Number: 6015475

CAS Registry Number: 53581-53-6 Type of Substance: isocyclic Molecular Formula: BrH*C11H16BrNO2

Linear Structure Formula: C11H16BrNO2*BrH Molecular Weight: 355.069

InChI Key: KOUBEZAODVTFTG-UHFFFAOYSA-N

0 prep out of 2 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+/-)-1-(2,5-dimethoxy-4-bromophenyl)propan-2-amine hydrobromide, 1-(2,4-dimethoxy-4-bromophenyl)-2-aminopropane hydrobromide, 1-(4bromo-2,5-dimethoxyphenyl)-2-aminopropane hydrobromide Identification Substance Label (3) Label

Reference

Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 10 p. 2545 - 2552 Title/Abstract Full Text View citing articles Show Details

(+/-)-DOB

Odagaki; Fuxe

Identification Physical Data (2) Bioactivity (3)

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 1 p. 337 - 344 Title/Abstract Full Text View citing articles Show Details

DOB*HBr, 1a*HBr

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

Physical Data Melting Point (2) Melting Point

Solvent (Melting Point)

Reference

175 - 177 °C

ethanol

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

145 - 146 °C

ethyl acetate

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Bioactivity Pharmacological Data (3) 1 of 3

2 of 3

3 of 3

Comment (Pharmacological Data)

Bioactivities present

Reference

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 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; Dukat; El-Bermawy; Law; De los Angeles; Teitler; King; Herrick-Davis

Journal of Medicinal Chemistry, 1994 , vol. 37, # 13 p. 1929 - 1935 Title/Abstract Full Text View citing articles Show Details

Odagaki; Fuxe

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 1 p. 337 - 344 Title/Abstract Full Text View citing articles Show Details

Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 10 p. 2545 - 2552 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

HEK cell membranes

Method (Pharmacological Data)

radioligand binding assay; in triplicate; assay tubes containing membranes, 2.5 nmol/l <3H>5-HT and varying concentrations of title comp. incubated for 20 min at 37 deg C; suspensions filtered and counted in liquid scintillation counter

Further Details (Pharmacological Data)

HEK cells stably expressing human 5-HT1E receptor; methiothepin (10 μmol/l) used to define nonspecific binding; 5-HT, serotonin

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

580 nmol/l

Reference

Dukat, Malgorzata; Smith, Carol; Herrick-Davis, Katharine; Teitler, Milt; Glennon, Richard A.

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 10 p. 2545 - 2552 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological

Sprague-Dawley rat hippocampal membrane

Data) Sex

male

Concentration (Pharmacological Data)

0.001 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

dose in 25 μl assay buffer

Method (Pharmacological Data)

rat weight 200 - 250 g; decapitation; hippocampal membrane isolation; title comp. 15 min incubation at 30 deg C with 0.3 μmol/l <γ-32P>GTP and 2 mmol/l MgCl2; <32P>phosphate determined by liquid scintillation

Further Details (Pharmacological Data)

GTP hydrolysis by high-affinity GTPase in 5-HT1A receptor-coupled G protein

Comment (Pharmacological Data)

No effect

Reference

Odagaki; Fuxe

Journal of Pharmacology and Experimental Therapeutics, 1995 , vol. 274, # 1 p. 337 - 344 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 6796103

Type of Substance: isocyclic Molecular Formula: BrH*C11H16BrNO2

Linear Structure Formula: C11H16BrNO2*BrH Molecular Weight: 355.069

InChI Key: KOUBEZAODVTFTG-FJXQXJEOSA-N

no reactions.

Physical Data (2)

Synthesize | Hide Details Find similar

Physical Data Melting Point (1) Melting Point

Reference

144 °C

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Optical Rotatory Power (1) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

2 g/100ml

H2O

13 deg

589 nm

25 °C

Reaxys Registry Number: 6796104

Type of Substance: isocyclic Molecular Formula: BrH*C11H16BrNO2

Linear Structure Formula: C11H16BrNO2*BrH Molecular Weight: 355.069

InChI Key: KOUBEZAODVTFTG-OGFXRTJISA-N

Reference Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

no reactions.

Physical Data (2)

Synthesize | Hide Details Find similar

Physical Data Melting Point (1) Melting Point

Reference

145 °C

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Optical Rotatory Power (1) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

2 g/100ml

H2O

-12 deg

589 nm

25 °C

Reference Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details