1-(1,3-benzodioxol-5-yl)propan-2-amine (MDA)

Reaxys

PubChem

eMolecules

Reactions (164)

Substances (11)

Structure

Citations (262)

Structure/Compound Data Chemical Name: 3,4-methylenedioxyamphetamine Reaxys Registry Number: 150196

CAS Registry Number: 4764-17-4 Type of Substance: heterocyclic Molecular Formula: C10H13NO2

Linear Structure Formula: C10H13NO2

Molecular Weight: 179.219

InChI Key: NGBBVGZWCFBOGO-UHFFFAOYSA-N

1

N° of preparations All Preps | All Reactions 26 prep out of 122 reactions.

Available Data

N° of ref.

Identification Physical Data (22) Spectra (18) Bioactivity (76) Other Data (7)

238

Synthesize | Hide Details Find similar Chemical Names and Synonyms 3,4-methylenedioxyamphetamine, (R/S)-1-(3,4-methylenedioxyphenyl)-2-amino-propane, (+/-)-Tenamfetamine, Tenamphetamine, 3,4methylenedioxyphenylisopropylamine, (±)-MDA, 3,4-MDA Identification Substance Label (6) Label

Reference

MDA

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. 412 - 426 Title/Abstract Full Text View citing articles Show Details

Cirimele; Kintz; Mangin

Archives of Toxicology, 1995 , vol. 70, # 1 p. 68 - 69 Title/Abstract Full Text View citing articles Show Details

Nakahara, Yuji; Kikura, Ruri

Archives of Toxicology, 1996 , vol. 70, # 12 p. 841 - 849 Title/Abstract Full Text View citing articles Show Details

Nakahara; Takahashi; Kikura

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 9 p. 1223 - 1227 Title/Abstract Full Text View citing articles Show Details

Miller, R. Timothy; Lau, Serrine S.; Monks, Terrence J.

Chemical Research in Toxicology, 1996 , vol. 9, # 2 p. 457 - 465 Title/Abstract Full Text View citing articles Show Details

Segura; Ortuno; Farre; Mc Lure; Pujadas; Pizarro; Llebaria; Joglar; Roset; De la Torre

Chemical Research in Toxicology, 2001 , vol. 14, # 9 p. 1203 - 1208 Title/Abstract Full Text View citing articles Show Details

Chu, Teresa; Kumagai, Yoshito; DiStefano, Emma W.; Cho, Arthur K.

Biochemical Pharmacology, 1996 , vol. 51, # 6 p. 789 - 796 Title/Abstract Full Text View citing articles Show Details

Pihlainen, Katja; Grigoras, Kestutis; Franssila, Sami; Ketola, Raimo; Kotiaho, Tapio; Kostiainen, Risto

Journal of Mass Spectrometry, 2005 , vol. 40, # 4 p. 539 - 545 Title/Abstract Full Text View citing articles Show Details

Castiglioni, Sara; Zuccato, Ettore; Crisci, Elisabetta; Chiabrando, Chiara; Fanelli, Roberte; Bagnati, Renzo

Analytical Chemistry, 2006 , vol. 78, # 24 p. 8421 - 8429 Title/Abstract Full Text View citing articles Show Details

Montesano, Camilla; Sergi, Manuel; Moro, Mariaelena; Napoletano, Sabino; Romolo, Francesco Saverio; Carlo, Michele Del; Compagnone, Dario; Curini, Roberta

Journal of Mass Spectrometry, 2013 , vol. 48, # 1 p. 49 - 59 Title/Abstract Full Text View citing articles Show Details

Concheiro, Marta; Baumann, Michael H.; Scheidweiler, Karl B.; Rothman, Richard B.; Marrone, Gina F.; Huestis, Marilyn A.

Drug Metabolism and Disposition, 2014 , vol. 42, # 1 p. 119 - 125 Title/Abstract Full Text View citing articles Show Details

7

Pifl, Christian; Nagy, Gabor; Berenyi, Sandor; Kattinger, Alexandra; Reither, Harald; Antus, Sandor

Journal of Pharmacology and Experimental Therapeutics, 2005 , vol. 314, # 1 p. 346 - 354 Title/Abstract Full Text View citing articles Show Details

R/S-MDA

Keizers, Peter H. J.; De Graaf, Chris; De Kanter, Frans J. J.; Oostenbrink, Chris; Feenstra, K. Anton; Commandeur, Jan N. M.; Vermeulen, Nico P. E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 19 p. 6117 - 6127 Title/Abstract Full Text View citing articles Show Details

Fig. 1., Negwer8 2229

Jones, Douglas C.; Lau, Serrine S.; Monks, Terrence J.

Journal of Pharmacology and Experimental Therapeutics, 2004 , vol. 311, # 1 p. 298 - 306 Title/Abstract Full Text View citing articles Show Details

II; MDA

Bai; Jones; Lau; Monks

Chemical Research in Toxicology, 2001 , vol. 14, # 7 p. 863 - 870 Title/Abstract Full Text View citing articles Show Details

2a

Borth, Swantje; Haensel, Wolfram; Roesner, Peter; Junge, Thomas

Journal of Mass Spectrometry, 2000 , vol. 35, # 6 p. 705 - 710 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (2) Prophetic Compound

Related Markush Structure (RN)

prophetic product

11337200

Location in Patent

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

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

Claim

Hosick; Thomas A.

Patent: US4120976 A1, 1978 ; Title/Abstract Full Text Show Details

Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US2003/119083 A1, 2003 ; Title/Abstract Full Text Show Details

Ekins, Sean

Patent: US2002/13372 A1, 2002 ; Title/Abstract Full Text Show Details

Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US2001/51158 A1, 2001 ; Title/Abstract Full Text Show Details

Derivative (12) Derivative

Comment (Derivative)

Reference

De Boer; Tan; Gorter; Van de Wal; Kettenesvan den Bosch; De Bruijn; Maes

Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 - 1246 Title/Abstract Full Text View citing articles Show Details

(+/-)-Tenamfetamine hydrochloride; N-(2Benzo[1,3]dioxol-5-yl-1-methyl-ethyl)-2,2,2-trifluoroacetamide

Trifluoracetamid: MS

Midha et al.

Journal of Pharmaceutical Sciences, 1976 , vol. 65, p. 188,190,193 Full Text View citing articles Show Details

Isopropyliden-Verb.: MS

Midha et al.

Journal of Pharmaceutical Sciences, 1976 , vol. 65, p. 188,190,193 Full Text View citing articles Show Details

Isopropylidenverbindung: MS

Midha et al.

Journal of Pharmaceutical Sciences, 1976 , vol. 65, p. 188,190,193 Full Text View citing articles Show Details

Hydrochlorid: F.: 180-181grad

Butterick; Unrau

Journal of the Chemical Society, Chemical Communications, 1974 , p. 307 Full Text View citing articles Show Details

Hydrochloridsalz: F:180-181grad

Butterick; Unrau

Journal of the Chemical Society, Chemical Communications, 1974 , p. 307 Full Text View citing articles Show Details

Benzoylderivat: F: 106-106.5grad

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 31 Chem.Abstr., 1963 , vol. 58, # 3334 Full Text View citing articles Show Details

Benzoylderivat: F.: 106-106.5grad

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 31 Chem.Abstr., 1963 , vol. 58, # 3334 Full Text View citing articles Show Details

N-Benzoylderivat: F: 106-106.5grad

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 257,260 Chem.Abstr., 1964 , vol. 60, # 4147 Full Text Show Details

N-Benzoylderivat: F.: 106-106.5grad

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 257,260 Chem.Abstr., 1964 , vol. 60, # 4147 Full Text Show Details

Sulfat: aus α-(3,4-Methylendioxyphenyl)-β-brom-propan 1) NH3, Ethanol, CuO, Δ (im geschmolzenen Rohr) 2) H2SO4

Muszynski

Acta Poloniae Pharmaceutica, 1961 , vol. 18, p. 471,474 Full Text Show Details

Sulfat: aus α-(3,4-Methylendioxyphenyl)-β-brom-propan 1.) erhitzen mit NH3/Ethanol/CuO im geschmolzenen Rohr, 2.) H2SO4

Muszynski

Acta Poloniae Pharmaceutica, 1961 , vol. 18, p. 471,474 Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

181 - 182 °C

Ho,B.T. et al.

Journal of Medicinal Chemistry, 1970 , vol. 13, p. 26 - 30 Full Text View citing articles Show Details

Boiling Point (7) Boiling Point

Pressure (Boiling Point)

Reference

89 - 91 °C

0.7 Torr

Ibanez Paniello

Anales de Quimica (1968-1979), 1976 , vol. 72, p. 814,815,817 Full Text Show Details

148 - 150 °C

12 Torr

Bernhard,H.O.; Snieckus,V.

Tetrahedron, 1971 , vol. 27, p. 2091 - 2100 Full Text View citing articles Show Details

155 - 160 °C

16 Torr

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 31 Chem.Abstr., 1963 , vol. 58, # 3334 Full Text View citing articles Show Details

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 257,260 Chem.Abstr., 1964 , vol. 60, # 4147 Full Text Show Details

152 °C

17 Torr

Govindan

Proceedings - Indian Academy of Sciences, Section A, 1956 , # 44 p. 126,127 Full Text Show Details

122 - 127 °C

5 Torr

Fujisawa; Deguchi

Yakugaku Zasshi, 1954 , vol. 74, p. 977,979 Chem.Abstr., 1955 , p. 10959 Full Text Show Details

143 - 145 °C

11 Torr

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427 Full Text Show Details

157 °C

22 Torr

Mannich; Jacobsohn

Chemische Berichte, 1910 , vol. 43, p. 193 Full Text View citing articles Show Details

Refractive Index (2) Refractive Index

Wavelength (Refractive Index)

Temperature (Refractive Index)

Reference

1.538

589 nm

20 °C

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 31 Chem.Abstr., 1963 , vol. 58, # 3334 Full Text View citing articles Show Details

1.5394

589 nm

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427 Full Text Show Details

Density (1) Density

Reference Temperature

Measurement Temperature

Reference

1.1277 g·cm-3

4 °C

25 °C

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427 Full Text Show Details

Association (MCS) (1) Description (Association (MCS))

Partner (Association (MCS))

Solvent (Association (MCS))

Temperature (Association (MCS))

Stability constant of the complex with ...

melanin

dimethylsulfoxide aq. phosphate buffer

36 °C

Reference Nakahara; Takahashi; Kikura

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 9 p. 1223 - 1227 Title/Abstract Full Text View citing articles Show Details

Chromatographic Data (4) Chromatographic data

Reference

LC (Liquid chromatography)

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, Oh-Seung; Lee, Jaeick

Rapid Communications in Mass Spectrometry, 2015 , vol. 29, # 4 p. 367 - 384 Title/Abstract Full Text View citing articles Show Details

Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, Oh-Seung; Lee, Jaeick

Rapid Communications in Mass Spectrometry, 2015 , vol. 29, # 4 p. 367 - 384 Title/Abstract Full Text Show Details

GC (Gas chromatography)

Pakniyat, Ehsan; Mousavi, Mehdi

Journal of the Chinese Chemical Society, 2014 , vol. 61, # 6 p. 649 - 658 Title/Abstract Full Text View citing articles Show Details

UPLC (Ultra performance liquid chromatography)

Lin, Huei-Ru; Liao, Chao-Chuan; Lin, Tzu-Chieh

Rapid Communications in Mass Spectrometry, 2014 , vol. 28, # 19 p. 2043 - 2053 Title/Abstract Full Text View citing articles Show Details

HPLC (High performance liquid chromatography)

Montesano, Camilla; Sergi, Manuel; Moro, Mariaelena; Napoletano, Sabino; Romolo, Francesco Saverio; Carlo, Michele Del; Compagnone, Dario; Curini, Roberta

Journal of Mass Spectrometry, 2013 , vol. 48, # 1 p. 49 - 59 Title/Abstract Full Text View citing articles Show Details

Dissociation Exponent (2) Temperature (Dissociation Exponent)

Solvent (Dissociation Exponent)

Method (Dissociation Exponent)

9.7

a1/apparent

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc

Environmental Science and Technology, 2008 , vol. 42, # 18 p. 6809 - 6816 Title/Abstract Full Text View citing articles Show Details

4.33

25 °C

H2O

potentiometric

b/apparent

Leffler et al.

Journal of the American Chemical Society, 1951 , vol. 73, p. 2611 Full Text View citing articles Show Details

Dissociation Exponent (pK)

Type (Dissociation Exponent)

Reference

Further Information (2) Description (Further Information)

Reference

Further information

Midha et al.

Journal of Pharmaceutical Sciences, 1976 , vol. 65, p. 188,190,193 Full Text View citing articles Show Details

Further information

Muszynski

Acta Poloniae Pharmaceutica, 1961 , vol. 18, p. 471,474 Full Text 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

Partition octan-1-ol/water (MCS) (1) log POW

Reference

1.64

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc

Environmental Science and Technology, 2008 , vol. 42, # 18 p. 6809 - 6816 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Reference

NMR

Ibanez Paniello

Anales de Quimica (1968-1979), 1976 , vol. 72, p. 814,815,817 Full Text Show Details

IR Spectroscopy (1)

Description (IR Spectroscopy)

Reference

IR

Ibanez Paniello

Anales de Quimica (1968-1979), 1976 , vol. 72, p. 814,815,817 Full Text Show Details

Mass Spectrometry (16)

Description (Mass Spectrometry)

Comment (Mass Spectrometry)

electrospray ionisation (ESI) spectrum

Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, Oh-Seung; Lee, Jaeick

Rapid Communications in Mass Spectrometry, 2015 , vol. 29, # 4 p. 367 - 384 Title/Abstract Full Text View citing articles Show Details

liquid chromatography mass spectrometry (LCMS) electrospray ionisation (ESI) spectrum

Jeong, Eun Sook; Kim, So-Hee; Cha, Eun-Ju; Lee, Kang Mi; Kim, Ho Jun; Lee, Sang-Won; Kwon, Oh-Seung; Lee, Jaeick

Rapid Communications in Mass Spectrometry, 2015 , vol. 29, # 4 p. 367 - 384 Title/Abstract Full Text Show Details

liquid chromatography mass spectrometry (LCMS) CID (collision-induced dissociation) spectrum

Lin, Huei-Ru; Liao, Chao-Chuan; Lin, Tzu-Chieh

Rapid Communications in Mass Spectrometry, 2014 , vol. 28, # 19 p. 2043 - 2053 Title/Abstract Full Text View citing articles Show Details

spectrum

Espy, Ryan D.; Teunissen, Sebastiaan Frans; Manicke, Nicholas E.; Ren, Yue; Ouyang, Zheng; Van Asten, Arian; Cooks, R. Graham

Analytical Chemistry, 2014 , vol. 86, # 15 p. 7712 - 7718 Title/Abstract Full Text View citing articles Show Details

liquid chromatography mass spectrometry (LCMS) tandem mass spectrometry spectrum

Montesano, Camilla; Sergi, Manuel; Moro, Mariaelena; Napoletano, Sabino; Romolo, Francesco Saverio; Carlo, Michele Del; Compagnone, Dario; Curini, Roberta

Journal of Mass Spectrometry, 2013 , vol. 48, # 1 p. 49 - 59 Title/Abstract Full Text View citing articles Show Details

tandem mass spectrometry electrospray ionisation (ESI) high resolution mass spectrometry (HRMS) spectrum

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

electrospray ionisation (ESI) high resolution mass spectrometry (HRMS) spectrum

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

TOFMS (Time of flight mass spectrum) ESI (Electrospray ionisation) Spectrum

Bijlsma, Lubertus; Sancho, Juan V.; Hernandez, Felix; Niessen, Wilfried M.A.

Journal of Mass Spectrometry, 2011 , vol. 46, # 9 p. 865 - 875 Title/Abstract Full Text View citing articles Show Details

HRMS (High resolution mass spectrometry) TOFMS (Time of flight mass spectrum) ESI (Electrospray ionisation) LCMS (Liquid chromatography mass spectrometry) Spectrum

Vonaparti; Lyris; Angelis; Panderi; Koupparis; Tsantili-Kakoulidou; Peters; Nielen; Georgakopoulos

Rapid Communications in Mass Spectrometry, 2010 , vol. 24, # 11 p. 1595 - 1609 Title/Abstract Full Text View citing articles Show Details

APCI (atmospheric pressure chemical ionization) Spectrum

Inoue, Hiroyuki; Hashimoto, Hiroaki; Watanabe, Susumu; Iwata, Yuko T.; Kanamori, Tatsuyuki; Miyaguchi, Hajime; Tsujikawa, Kenji; Kuwayama, Kenji; Tachi, Noriyuki; Uetake, Naohito

Journal of Mass Spectrometry, 2009 , vol. 44, # 9 p. 1300 - 1307 Title/Abstract Full Text View citing articles Show Details

APCI (atmospheric pressure chemical ionization) Tandem mass spectrometry Spectrum

Inoue, Hiroyuki; Hashimoto, Hiroaki; Watanabe, Susumu; Iwata, Yuko T.; Kanamori, Tatsuyuki; Miyaguchi, Hajime; Tsujikawa, Kenji; Kuwayama, Kenji; Tachi, Noriyuki; Uetake, Naohito

Journal of Mass Spectrometry, 2009 , vol. 44, # 9 p. 1300 - 1307 Title/Abstract Full Text View citing articles Show Details

Reference

LCMS (Liquid chromatography mass spectrometry) ESI (Electrospray ionisation) Tandem mass spectrometry Spectrum

mol peak

Thoerngren, John-Olof; Oestervall, Fredrik; Garle, Mats

Journal of Mass Spectrometry, 2008 , vol. 43, # 7 p. 980 - 992 Title/Abstract Full Text View citing articles Show Details

spectrum tandem mass spectrometry

Pihlainen, Katja; Grigoras, Kestutis; Franssila, Sami; Ketola, Raimo; Kotiaho, Tapio; Kostiainen, Risto

Journal of Mass Spectrometry, 2005 , vol. 40, # 4 p. 539 - 545 Title/Abstract Full Text View citing articles Show Details

spectrum collision-induced dissociation tandem mass spectrometry

Borth, Swantje; Haensel, Wolfram; Roesner, Peter; Junge, Thomas

Journal of Mass Spectrometry, 2000 , vol. 35, # 6 p. 705 - 710 Title/Abstract Full Text View citing articles Show Details

chemical ionization (CI) electron impact (EI)

Borth, Swantje; Haensel, Wolfram; Roesner, Peter; Junge, Thomas

Journal of Mass Spectrometry, 2000 , vol. 35, # 6 p. 705 - 710 Title/Abstract Full Text View citing articles Show Details

Midha et al.

Journal of Pharmaceutical Sciences, 1976 , vol. 65, p. 188,190,193 Full Text View citing articles Show Details

Bioactivity Pharmacological Data (76) 1 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

Hosick; Thomas A.

Patent: US4120976 A1, 1978 ; Title/Abstract Full Text Show Details

Ho,B.T. et al.

Journal of Medicinal Chemistry, 1970 , vol. 13, p. 26 - 30 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

Bernhard,H.O.; Snieckus,V.

Tetrahedron, 1971 , vol. 27, p. 2091 - 2100 Full Text View citing articles Show Details

Walker,G.N.; Kempton,R.J.

Journal of Organic Chemistry, 1971 , vol. 36, p. 1413 - 1416 Full Text View citing articles Show Details

Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US2003/119083 A1, 2003 ; 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

Merck

Patent: DE274350 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 768 Full Text Show Details

Decker; Becker

Justus Liebigs Annalen der Chemie, 1913 , vol. 395, p. 335 Chem. Zentralbl., 1914 , vol. 85, # I p. 89 Full Text View citing articles Show Details

Rosenmund

Chem. Zentralbl., 1919 , vol. 90, # I p. 953 Full Text Show Details

Merck

Patent: DE273323 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 761 Full Text Show Details

Decker

Patent: DE267699 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 999 Full Text Show Details

Rosenmund

Patent: DE336153 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 884 Full Text Show Details

Rosenmund

Patent: DE320480 ;

Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 883 Full Text Show Details

Bruckner

Justus Liebigs Annalen der Chemie, 1935 , vol. 518, p. 226,241 Full Text View citing articles Show Details

Dobrowsky

Monatshefte fuer Chemie, 1951 , vol. 82, p. 122,134 Full Text View citing articles Show Details

Hey; Williams

Journal of the Chemical Society, 1951 , p. 1527,1529 Full Text View citing articles Show Details

Leffler et al.

Journal of the American Chemical Society, 1951 , vol. 73, p. 2611 Full Text View citing articles Show Details

Elks; Hey

Journal of the Chemical Society, 1943 , p. 15 Full Text View citing articles Show Details

Biel et al.

Journal of the American Chemical Society, 1954 , vol. 76, p. 3149,3151 Full Text View citing articles Show Details

2 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

Merck,E.

Patent: DE549967 , 1930 ; DRP/DRBP Org.Chem.

Full Text Show Details

Morimoto

Yakugaku Zasshi, 1952 , vol. 72, p. 1952> 99 Chem.Abstr., 1952 , p. 11207 Full Text View citing articles Show Details

Morimoto

Yakugaku Zasshi, 1952 , vol. 72, p. 1952> 95, 97 Chem.Abstr., 1952 , p. 582 Full Text View citing articles Show Details

Morimoto

Yakugaku Zasshi, 1952 , vol. 72, p. 1952> 95, 96 Chem.Abstr., 1952 , p. 582 Full Text View citing articles Show Details

Merck,E.

Patent: DE550122 , 1929 ; DRP/DRBP Org.Chem.

Full Text Show Details

Wolfes

Patent: US1941647 , 1930 ; Full Text Show Details

Dobrowsky

Monatshefte fuer Chemie, 1955 , vol. 86, p. 27 Full Text View citing articles Show Details

Govindan

Current Science, 1956 , vol. 25, p. 262 Full Text View citing articles Show Details

Kametani et al.

Yakugaku Zasshi, 1951 , vol. 71, p. 325,328 Chem.Abstr., 1952 , p. 4546 Full Text View citing articles Show Details

Kametani; Inagaki

Yakugaku Zasshi, 1954 , vol. 74, p. 417 Chem.Abstr., 1955 , p. 5495 Full Text View citing articles Show Details

Morimoto

Yakugaku Zasshi, 1952 , vol. 72, p. 1952> 102 Chem.Abstr., 1952 , p. 11207 Full Text View citing articles Show Details

Mannich; Jacobsohn

Chemische Berichte, 1910 , vol. 43, p. 193 Full Text View citing articles Show Details

Decker

Patent: DE281547 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 12, p. 756 Full Text Show Details

Merck,E.

Patent: DE551870 , 1930 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 18, p. 2766 Full Text Show Details

Fujisawa; Deguchi

Yakugaku Zasshi, 1954 , vol. 74, p. 977,979 Chem.Abstr., 1955 , p. 10959 Full Text Show Details

Merck,E.

Patent: DE549967 , 1930 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 19, p. 1113 Full Text Show Details

Fujisawa

Yakugaku Zasshi, 1945 , vol. 65, p. Ausg. B, S. 555, 563 Chem.Abstr., 1952 , p. 116 Full Text Show Details

Sugasawa et al.

Yakugaku Zasshi, 1940 , vol. 60, p. 140,142; engl. Ref. S. 39, 40 Chem.Abstr., 1940 , p. 5087 Full Text Show Details

Govindan

Proceedings - Indian Academy of Sciences, Section A, 1956 , # 44 p. 126,127 Full Text Show Details

Kametani; Inagaki

Yakugaku Zasshi, 1954 , vol. 74, p. 1040 Chem.Abstr., 1955 , p. 11 659 Full Text Show Details

3 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

Ohki

Yakugaku Zasshi, 1950 , vol. 70, p. 92,98 Chem.Abstr., 1950 , p. 5867 Full Text Show Details

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427 Full Text Show Details

Sugasawa et al.

Proceedings of the Imperial Academy (Tokyo), 1939 , vol. 15, p. 82,83,84 Yakugaku Zasshi, 1939 , vol. 59, p. 247,250 Chem.Abstr., 1939 , p. 6318 Full Text Show Details

Benington et al.

Journal of Organic Chemistry, 1958 , vol. 23, p. 1979,1980 Full Text Show Details

Kindler

Justus Liebigs Annalen der Chemie, 1923 , vol. 431, p. 213 Chem. Zentralbl., 1923 , vol. 94, # II p. 403 Full Text Show Details

Sugasawa; Sakurai; Sugimoto

Yakugaku Zasshi, 1939 , vol. 59, p. 247,250 Proceedings of the Imperial Academy (Tokyo), 1939 , vol. 15, p. 82,84 Chem. Zentralbl., 1939 , vol. 110, # II p. 3574 Full Text Show Details

Bernhard; Snieckus

Tetrahedron, 1971 , vol. 27, p. 2091,2097 Full Text Show Details

Barfknecht et al.

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

Nichols; Kostuba

Journal of Medicinal Chemistry, 1979 , vol. 22, # 10 p. 1264 - 1267 Title/Abstract Full Text View citing articles Show Details

Muszynski

Acta Poloniae Pharmaceutica, 1961 , vol. 18, p. 471,474 Full Text Show Details

Midha et al.

Journal of Pharmaceutical Sciences, 1976 , vol. 65, p. 188,190,193 Full Text View citing articles Show Details

Butterick; Unrau

Journal of the Chemical Society, Chemical Communications, 1974 , p. 307 Full Text View citing articles Show Details

Ibanez Paniello

Anales de Quimica (1968-1979), 1976 , vol. 72, p. 814,815,817 Full Text Show Details

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 31 Chem.Abstr., 1963 , vol. 58, # 3334 Full Text View citing articles Show Details

Biniecki et al.

Acta Poloniae Pharmaceutica, 1962 , vol. 19, p. 257,260 Chem.Abstr., 1964 , vol. 60, # 4147 Full Text Show Details

Rastogi, Shri Niwas; Kansal, V. K.; Bhaduri, A. P.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983 , vol. 22, # 3 p. 234 - 237 Title/Abstract Full Text Show Details

Fukuto; Kumagai; Cho

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

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4 of 76

5 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

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Comment (Pharmacological Data)

Bioactivities present

Reference

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6 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

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Antolino-Lobo, Irene; Meulenbelt, Jan; Nijmeijer, Sandra M.; Scherpenisse, Peter; Van Den Berg, Martin; Van Duursen, Majorie B. M.

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Journal of medicinal chemistry, 1966 , vol. 9, # 3 p. 273 - 280 Title/Abstract Full Text Show Details

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7 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

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Barfknecht; Nichols; Dunn III

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

Nichols; Ilhan; Long

Archives Internationales de Pharmacodynamie et de Therapie, 1975 , vol. 214, # 1 p. 133 - 140 Title/Abstract Full Text View citing articles Show Details

Kier; Hall

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

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Journal of Analytical Toxicology, 1998 , vol. 22, # 1 p. 33 - 39 Title/Abstract Full Text View citing articles Show Details

Parker; Marona-Lewicka; Kurrasch; Shulgin; Nichols

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

Miller; Lau; Monks

Chemical Research in Toxicology, 1996 , vol. 9, # 2 p. 457 - 465 Title/Abstract Full Text Show Details

Monte; Marona-Lewicka; Cozzi; Nichols

Journal of Medicinal Chemistry, 1993 , vol. 36, # 23 p. 3700 - 3706 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

Zaczek; Culp; Goldberg; Mccann; De Souza

The Journal of pharmacology and experimental therapeutics, 1991 , vol. 257, # 2 p. 820 - 829 Title/Abstract Full Text Show Details

McCann; Ricaurte

Brain research, 1991 , vol. 545, # 1-2 p. 279 - 282 Title/Abstract Full Text Show Details

Clare

Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 687 - 702 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

Psychopharmacology, 1988 , vol. 94, # 2 p. 213 - 216 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; Glennon; Titeler

Psychopharmacology, 1986 , vol. 88, # 4 p. 525 - 526 Title/Abstract Full Text Show Details

Nichols; Lloyd; Hoffman; Yim

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 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

Braun; Shulgin

Arzneimittel-Forschung/Drug Research, 1980 , vol. 30, # 5 p. 825 - 830 Title/Abstract Full Text View citing articles Show Details

Thiessen; Cook

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8 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

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M. A. Davis

Annual reports in medicinal chemistry, 1967 , vol. 3, p. 14 - 27 Title/Abstract Full Text Show Details

Warunya Arunotayanun; Jeffrey W. Dalley; Xi-Ping Huang; Vincent Setola; Ric Treble; Leslie Iversen; Bryan L. Roth; Simon Gibbons

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

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http://en.wikipedia.org/wiki/3,4-methylenedioxyamphetamine Full Text Show Details

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Fuchigami Yuki; Ikeda Rie; Kuzushima Miki; Wada Mitsuhiro; Kuroda Naotaka; Nakashima Kenichiro

European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 2013 , vol. 49, # 1 p. 57 - 64 Title/Abstract Full Text Show Details

Sandtner, Walter; Schmid, Diethart; Schicker, Klaus; Gerstbrein, Klaus; Koenig, Xaver; Mayer, Felix P.; Boehm, Stefan; Freissmuth, Michael; Sitte, Harald H.

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Pakniyat, Ehsan; Mousavi, Mehdi

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10 of 76

Comment (Pharmacological Data)

Bioactivities present

Reference

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Comment (Pharmacological Data)

Bioactivities present

Reference

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Journal of Food and Drug Analysis, 2016 , vol. 24, # 2 p. 264 - 276 Title/Abstract Full Text View citing articles Show Details

Asadullin, Azat R.; Yuldashev, Vladimir L.; Galeeva, Elena Kh.; Achmetova, Elvina A.; Nikolaev, Ivan V.

International Journal of Environmental and Science Education, 2016 , vol. 11, # 8 p. 1913 - 1922 Title/Abstract Full Text View citing articles Show Details

Asimakopoulos, Alexandros G.; Kannan, Kurunthachalam

Environmental Chemistry, 2016 , vol. 13, # 4 p. 541 - 576 Title/Abstract Full Text View citing articles Show Details

Pérez, Rocío L.; Escandar, Graciela M.

Sustainable Chemistry and Pharmacy, 2016 , vol. 4, p. 1 - 12 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

Camacho-Muñoz, Dolores; Petrie, Bruce; Castrignanò, Erika; Kasprzyk-Hordern, Barbara

Current Analytical Chemistry, 2016 , vol. 12, # 4 p. 303 - 314 Title/Abstract Full Text View citing articles Show Details

Giannoukos, Stamatios; Brkić, Boris; Taylor, Stephen; Marshall, Alan; Verbeck, Guido F.

Chemical Reviews, 2016 , vol. 116, # 14 p. 8146 - 8172 Title/Abstract Full Text View citing articles Show Details

Garcia-Romeu, Albert; Kersgaard, Brennan; Addy, Peter H.

Experimental and Clinical Psychopharmacology, 2016 , vol. 24, # 4 p. 229 - 268 Title/Abstract Full Text View citing articles Show Details

Rykowska; Wasiak

Open Chemistry, 2015 , vol. 13, # 1 p. 1353 - 1370 Title/Abstract Full Text View citing articles Show Details

Joya, Xavier; Marchei, Emilia; Salat-Batlle, Judith; García-Algar, Oscar; Calvaresi, Valeria; Pacifici, Roberta; Pichini, Simona

Drug Testing and Analysis, 2016 , vol. 8, # 8 p. 864 - 868 Title/Abstract Full Text View citing articles Show Details

Wang, De-Gao; Zheng, Qiu-Da; Wang, Xiao-Ping; Du, Juan; Tian, Chong-Guo; Wang, Zhuang; Ge, Lin-Ke

Environmental Science and Pollution Research, 2016 , vol. 23, # 16 p. 16495 - 16503 Title/Abstract Full Text View citing articles Show Details

Pitterl, Florian; Köb, Sebastian; Pitterle, Johanna; Steger, Julia; Oberacher, Herbert

LC-GC Europe, 2016 , vol. 29, # 8 p. 419 - 427 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

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Comment (Pharmacological Data)

Bioactivities present

Reference

Senta, Ivan; Krizman, Ivona; Ahel, Marijan; Terzic, Senka

Journal of Chromatography A, 2015 , vol. 1425, p. 204 - 212 Title/Abstract Full Text View citing articles Show Details

Gentili, Stefano; Solimini, Renata; Tittarelli, Roberta; Mannocchi, Giulio; Busardò, Francesco Paolo

Journal of Analytical Methods in Chemistry, 2016 , vol. 2016, art. no. 1234581 Title/Abstract Full Text Show Details

Toselli, Francesca; Dodd, Peter R.; Gillam, Elizabeth M. J.

Drug Metabolism Reviews, 2016 , vol. 48, # 3 p. 379 - 404 Title/Abstract Full Text Show Details

Golovko; Bonitenko, E. Yu.; Ivanov; Barinov; Zatsepin

Neurochemical Journal, 2016 , vol. 10, # 3 p. 173 - 183 Title/Abstract Full Text Show Details

Mowry, James B.; Spyker, Daniel A.; Cantilena, Louis R.; McMillan, Naya; Ford, Marsha

Clinical Toxicology, 2014 , vol. 52, # 10 p. 1032 - 1283 Title/Abstract Full Text Show Details

Nelson, Zachary J.; Stellpflug, Samuel J.; Engebretsen, Kristin M.

Journal of Pharmacy Practice, 2016 , vol. 29, # 5 p. 516 - 526 Title/Abstract Full Text Show Details

Petrie, Bruce; Gravell, Anthony; Mills, Graham A.; Youdan, Jane; Barden, Ruth; Kasprzyk-Hordern, Barbara

Environmental Science and Technology, 2016 , vol. 50, # 17 p. 9469 - 9478 Title/Abstract Full Text Show Details

Görgens, Christian; Guddat, Sven; Thomas, Andreas; Wachsmuth, Philipp; Orlovius, Anne-Katrin; Sigmund, Gerd; Thevis, Mario; Schänzer, Wilhelm

Journal of Pharmaceutical and Biomedical Analysis, 2016 , vol. 131, p. 482 - 496 Title/Abstract Full Text Show Details

Camacho-Muñoz, Dolores; Petrie, Bruce; Castrignanò, Erika; Kasprzyk-Hordern, Barbara

Current Analytical Chemistry, 2016 , vol. 12, # 4 p. 303 - 314 Title/Abstract Full Text Show Details

Van Buskirk, Joe; Roxburgh, Amanda; Bruno, Raimondo; Naicker, Sundresan; Lenton, Simon; Sutherland, Rachel; Whittaker, Elizabeth; Sindicich, Natasha; Matthews, Allison; Butler, Kerryn; Burns, Lucinda

International Journal of Drug Policy, 2016 , vol. 35, p. 32 - 37

Title/Abstract Full Text Show Details

Kyriakou, Chrystalla; Marchei, Emilia; Scaravelli, Giulia; García-Algar, Oscar; Supervía, August; Graziano, Silvia

Journal of Pharmaceutical and Biomedical Analysis, 2016 , vol. 128, p. 53 - 60 Title/Abstract Full Text Show Details

Gentili, Stefano; Mortali, Claudia; Mastrobattista, Luisa; Berretta, Paolo; Zaami, Simona

Journal of Pharmaceutical and Biomedical Analysis, 2016 , vol. 129, p. 282 - 287 Title/Abstract Full Text Show Details

Andrés-Costa, María Jesús; Andreu, Vicente; Picó, Yolanda

Journal of Chromatography A, 2016 , vol. 1461, p. 98 - 106 Title/Abstract Full Text Show Details

Gökay, Sinem Sarı; Yıldızdaş, Rıza Dinçer; Sarı, Mehmet Yusuf; Çelik, Tuğce; Horoz, Özden Özgür; Yılmaz, Hayri Levent

Hong Kong Journal of Emergency Medicine, 2016 , vol. 23, # 4 p. 238 - 241 Title/Abstract Full Text Show Details

Peng, Yan; Hall, Sarah; Gautam, Lata

TrAC - Trends in Analytical Chemistry, 2016 , vol. 85, p. 232 - 240 Title/Abstract Full Text Show Details

Haglock-Adler, Carrie J.; McMillin, Gwendolyn A.; Strathmann, Frederick G.

Clinical Biochemistry, 2016 , vol. 49, # 13-14 p. 1092 - 1095 Title/Abstract Full Text Show Details

Salomone; Tsanaclis; Agius; Kintz; Baumgartner

Drug Testing and Analysis, 2016 , vol. 8, # 10 p. 996 - 1004 Title/Abstract Full Text Show Details

Tiscione, Nicholas B.; Miller, Russell; Shan, Xiaoqin; Sprague, Jessica; Yeatman, Dustin Tate

Journal of Analytical Toxicology, 2016 , vol. 40, # 8 art. no. BKW063, p. 639 - 648 Title/Abstract Full Text Show Details

Khalilian, Faezeh; Rezaee, Mohammad

Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 11 p. 2105 - 2113 Title/Abstract Full Text Show Details

Chen, Pai-Shan; Chen, Shu-Hua; Chen, Jung-Hsuan; Haung, Wan-Yun; Liu, Hsin-Tung; Kong, Po-Hsin; Yang, Olivia HsuYuan

Analytica Chimica Acta, 2016 , vol. 946, p. 1 - 8 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Saka, Cafer

Critical Reviews in Analytical Chemistry, 2017 , vol. 47, # 1 p. 1 - 23 Title/Abstract Full Text Show Details

Boileau, Isabelle; Payer, Doris; Rusjan, Pablo M.; Houle, Sylvain; Tong, Junchao; McCluskey, Tina; Wilson, Alan A.; Kish, Stephen J.

Neuropsychopharmacology, 2016 , vol. 41, # 13 p. 2994 - 3002 Title/Abstract Full Text Show Details

Argente-García; Jornet-Martínez; Herráez-Hernández; Campíns-Falcó

Analytica Chimica Acta, 2016 , vol. 943, p. 123 - 130 Title/Abstract Full Text Show Details

Zhang, Yan Victoria; Wei, Bin; Zhu, Yu; Zhang, Yanhua; Bluth, Martin H.

Clinics in Laboratory Medicine, 2016 , vol. 36, # 4 p. 635 - 661 Title/Abstract Full Text Show Details

Huang, Chuixiu; Gjelstad, Astrid; Pedersen-Bjergaard, Stig

Reviews in Analytical Chemistry, 2016 , vol. 35, # 4 p. 169 - 183 Title/Abstract Full Text Show Details

Balakrishna, Keshava; Rath, Amlan; Praveenkumarreddy, Yerabham; Guruge, Keerthi Siri; Subedi, Bikram

Ecotoxicology and Environmental Safety, 2017 , vol. 137, p. 113 - 120 Title/Abstract Full Text Show Details

Kinyua, Juliet; Negreira, Noelia; Miserez, Bram; Causanilles, Ana; Emke, Erik; Gremeaux, Lies; de Voogt, Pim; Ramsey, John; Covaci, Adrian; van Nuijs, Alexander L.N.

Science of the Total Environment, 2016 , vol. 573, p. 1527 - 1535 Title/Abstract Full Text Show Details

Bodnar Willard, Melissa A.; McGuffin, Victoria L.; Smith, Ruth Waddell

Forensic Science International, 2017 , vol. 270, p. 111 - 120 Title/Abstract Full Text Show Details

Krumbiegel, Franziska; Hastedt, Martin; Westendorf, Lena; Niebel, André; Methling, Maximilian; Parr, Maria Kristina; Tsokos, Michael

Forensic Science, Medicine, and Pathology, 2016 , vol. 12, # 4 p. 416 - 434 Title/Abstract Full Text Show Details

Lazenka; Suyama; Bauer; Banks; Negus

Pharmacology Biochemistry and Behavior, 2017 , vol. 152, p. 52 - 60 Title/Abstract Full Text Show Details

Sahai, Michelle A.; Davidson, Colin; Khelashvili, George; Barrese, Vincenzo; Dutta, Neelakshi; Weinstein, Harel; OpackaJuffry, Jolanta

Progress in Neuro-Psychopharmacology and Biological Psychiatry, 2017 , vol. 75, p. 1 - 9 Title/Abstract Full Text Show Details

Smith, Douglas A.; Blough, Bruce E.; Banks, Matthew L.

Psychopharmacology, 2017 , vol. 234, # 1 p. 117 - 127 Title/Abstract Full Text Show Details

Petrie, Bruce; Proctor, Kathryn; Youdan, Jane; Barden, Ruth; Kasprzyk-Hordern, Barbara

Science of the Total Environment, 2017 , vol. 579, p. 569 - 578 Title/Abstract Full Text Show Details

Mardal, Marie; Kinyua, Juliet; Ramin, Pedram; Miserez, Bram; Van Nuijs, Alexander L. N.; Covaci, Adrian; Meyer, Markus R.

Drug Testing and Analysis, 2017 , vol. 9, # 1 p. 106 - 114 Title/Abstract Full Text Show Details

Lendoiro, Elena; Jiménez-Morigosa, Cristian; Cruz, Angelines; Páramo, Mario; López-Rivadulla, Manuel; de Castro, Ana

Drug Testing and Analysis, 2017 , vol. 9, # 1 p. 96 - 105 Title/Abstract Full Text Show Details

Ayme-Dietrich, Estelle; Aubertin-Kirch, Gaëlle; Maroteaux, Luc; Monassier, Laurent

Archives of Cardiovascular Diseases, 2017 , vol. 110, # 1 p. 51 - 59 Title/Abstract Full Text Show Details

Maroteaux, Luc; Ayme-Dietrich, Estelle; Aubertin-Kirch, Gaëlle; Banas, Sophie; Quentin, Emily; Lawson, Roland; Monassier, Laurent

Pharmacology and Therapeutics, 2017 , vol. 170, p. 14 - 36 Title/Abstract Full Text Show Details

Petrie, Bruce; Smith, Benjamin D.; Youdan, Jane; Barden, Ruth; Kasprzyk-Hordern, Barbara

Analytica Chimica Acta, 2017 , vol. 959, p. 91 - 101 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.

Archives of Toxicology, 2016 , vol. 90, # 2 p. 305 - 318 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Rickli, Anna; Kopf, Simone; Hoener, Marius C; Liechti, Matthias E.

British Journal of Pharmacology, 2015 , vol. 172, # 13 p. 3412 - 3425 Title/Abstract Full Text View citing articles Show Details

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

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Sandtner, Walter; Schmid, Diethart; Schicker, Klaus; Gerstbrein, Klaus; Koenig, Xaver; Mayer, Felix P.; Boehm, Stefan; Freissmuth, Michael; Sitte, Harald H.

British Journal of Pharmacology, 2014 , vol. 171, # 4 p. 1007 - 1018 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Concheiro, Marta; Baumann, Michael H.; Scheidweiler, Karl B.; Rothman, Richard B.; Marrone, Gina F.; Huestis, Marilyn A.

Drug Metabolism and Disposition, 2014 , vol. 42, # 1 p. 119 - 125 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Goodwin, Amy K.; Mueller, Melanie; Shell, Courtney D.; Ricaurte, George A.; Ator, Nancy A.

Journal of Pharmacology and Experimental Therapeutics, 2013 , vol. 345, # 3 p. 342 - 353 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

HEK293 cells; genetically modified/infected with: human serotonin transporter

Further Details (Pharmacological Data)

neutral red assay; HEK: human embryonic kidney; effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

-3.2

Reference

McNamara, Yvonne M.; Cloonan, Suzanne M.; Knox, Andrew J.S.; Keating, John J.; Butler, Stephen G.; Peters, Guenther H.;

Meegan, Mary J.; Williams, D. Clive

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 3 p. 1328 - 1348 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK293 cells of human

Concentration (Pharmacological Data)

1 μmol/l - 1 mmol/l

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

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Reference

Cloonan, Suzanne M.; Keating, John J.; Corrigan, Desmond; O'Brien, John E.; Kavanagh, Pierce V.; Williams, D. Clive; Meegan, Mary J.

Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 11 p. 4009 - 4031 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK293 cells of human; genetically modified/infected with: human serotonin reuptake transporter

Concentration (Pharmacological Data)

1 μmol/l - 1 mmol/l

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

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-3.49

-3.16

Reference

Cloonan, Suzanne M.; Keating, John J.; Corrigan, Desmond; O'Brien, John E.; Kavanagh, Pierce V.; Williams, D. Clive; Meegan, Mary J.

Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 11 p. 4009 - 4031 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK293 cells of human; genetically modified/infected with: human noradrenaline reuptake transporter

Concentration (Pharmacological Data)

1 μmol/l - 1 mmol/l

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type

-3.23

(Pharmacological Data)

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Reference

Cloonan, Suzanne M.; Keating, John J.; Corrigan, Desmond; O'Brien, John E.; Kavanagh, Pierce V.; Williams, D. Clive; Meegan, Mary J.

Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 11 p. 4009 - 4031 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK293 cells of human; genetically modified/infected with: human dopamine reuptake transporter

Concentration (Pharmacological Data)

1 μmol/l - 1 mmol/l

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

-2.23

Reference

Cloonan, Suzanne M.; Keating, John J.; Corrigan, Desmond; O'Brien, John E.; Kavanagh, Pierce V.; Williams, D. Clive; Meegan, Mary J.

Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 11 p. 4009 - 4031 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

metastatic bone neuroblastoma derived SHSY-5Y cells of human

Concentration (Pharmacological Data)

1 μmol/l - 1 mmol/l

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

> -2

Reference

Cloonan, Suzanne M.; Keating, John J.; Corrigan, Desmond; O'Brien, John E.; Kavanagh, Pierce V.; Williams, D. Clive; Meegan, Mary J.

Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 11 p. 4009 - 4031 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

liver epithelial cells of human

Concentration (Pharmacological Data)

<= 10 mmol/l

Further Details (Pharmacological Data)

MTT assay

Type (Pharmacological

IC50

Data)

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Value of Type (Pharmacological Data)

2.7 mmol/l

Reference

Antolino-Lobo, Irene; Meulenbelt, Jan; Nijmeijer, Sandra M.; Scherpenisse, Peter; Van Den Berg, Martin; Van Duursen, Majorie B. M.

Drug Metabolism and Disposition, 2010 , vol. 38, # 7 p. 1105 - 1112 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

liver epithelial cells of human

Concentration (Pharmacological Data)

<= 10 mmol/l

Further Details (Pharmacological Data)

MTT assay

Type (Pharmacological Data)

maximal cell death after 24 h

Value of Type (Pharmacological Data)

69.6 percent

Reference

Antolino-Lobo, Irene; Meulenbelt, Jan; Nijmeijer, Sandra M.; Scherpenisse, Peter; Van Den Berg, Martin; Van Duursen, Majorie B. M.

Drug Metabolism and Disposition, 2010 , vol. 38, # 7 p. 1105 - 1112 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

protein binding affinity

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK-293 TRex cells of human; genetically modified/infected with: rat serotonin transporter

Concentration (Pharmacological Data)

1 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

not clear from article whether title comp. or its hydrochloride used

Further Details (Pharmacological Data)

inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.996 μmol/l

Reference

Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G.; Knox, Andrew J.S.; Jorgensen, Anne M.; Peters, Guenther H.; Rai, Dilip; Corrigan, Desmond; Lloyd, David G.; Williams, D. Clive; Meegan, Mary J.

European Journal of Medicinal Chemistry, 2009 , vol. 44, # 12 p. 4862 - 4888 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

protein binding affinity

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK-293 TRex cells of human; genetically modified/infected with: rat serotonin transporter

Concentration (Pharmacological Data)

1 - 100 μmol/l

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Kind of Dosing (Pharmacological Data)

not clear from article whether title comp. or its hydrochloride used

Results

molecular target: serotonin transporter

Reference

Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G.; Knox, Andrew J.S.; Jorgensen, Anne M.; Peters, Guenther H.; Rai, Dilip; Corrigan, Desmond; Lloyd, David G.; Williams, D. Clive; Meegan, Mary J.

European Journal of Medicinal Chemistry, 2009 , vol. 44, # 12 p. 4862 - 4888 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK-293 cells of human

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

-3.49

Reference

Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G.; Knox, Andrew J.S.; Jorgensen, Anne M.; Peters, Guenther H.; Rai, Dilip; Corrigan, Desmond; Lloyd, David G.; Williams, D. Clive; Meegan, Mary J.

European Journal of Medicinal Chemistry, 2009 , vol. 44, # 12 p. 4862 - 4888 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

neuroblastoma SH-SY5Y cells of human

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

> -2

Reference

Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G.; Knox, Andrew J.S.; Jorgensen, Anne M.; Peters, Guenther H.; Rai, Dilip; Corrigan, Desmond; Lloyd, David G.; Williams, D. Clive; Meegan, Mary J.

European Journal of Medicinal Chemistry, 2009 , vol. 44, # 12 p. 4862 - 4888 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

Burkitt's lymphoma DG-75 cells of human

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

-2.72

Reference

Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G.; Knox, Andrew J.S.; Jorgensen, Anne M.; Peters, Guenther H.; Rai, Dilip; Corrigan, Desmond; Lloyd, David G.; Williams, D. Clive; Meegan, Mary J.

European Journal of Medicinal Chemistry, 2009 , vol. 44, # 12 p. 4862 - 4888

Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic kidney HEK-293 cells of human; genetically modified/infected with: human serotonin transporter

Further Details (Pharmacological Data)

effective concentration (EC)

Type (Pharmacological Data)

log EC50

Value of Type (Pharmacological Data)

-3.16

Reference

Cloonan, Suzanne M.; Keating, John J.; Butler, Stephen G.; Knox, Andrew J.S.; Jorgensen, Anne M.; Peters, Guenther H.; Rai, Dilip; Corrigan, Desmond; Lloyd, David G.; Williams, D. Clive; Meegan, Mary J.

European Journal of Medicinal Chemistry, 2009 , vol. 44, # 12 p. 4862 - 4888 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neurotoxicity

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp dissolved in water

Method (Pharmacological Data)

rats (mdr1a (+/+)) pretreated with fluoxetine for 4 days and on d 4 administered with title comp.; killed at pre dose and post dose at 0.25-10 h; brain and plasma collected; title comp. conc. in brain and plasma determined by HPLC-FD

Further Details (Pharmacological Data)

control: mice administered with saline for 4 days and on d 4 administered with 10 ml/kg title comp.; fluoxetine dissolved in saline

Results

title comp. conc. in both plasma and brain were lower in Fluoxetine treated mice than control up to 2 h and increased after 4 h than control; figure; table

Reference

Upreti, Vijay V.; Eddington, Natalie D.

Journal of Pharmaceutical Sciences, 2008 , vol. 97, # 4 p. 1593 - 1605 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

10 mg/kg

Kind of Dosing (Pharmacological Data)

title comp dissolved in water

Method

rats (mdr1a (+/+)) pretreated with fluoxetine for 4 days and on d 4 administered with title comp.; killed at pre dose and post dose at

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(Pharmacological Data)

0.25-10 h; elimination half life in brain and plasma determined

Further Details (Pharmacological Data)

control: mice administered with saline for 4 days and on d 4 administered with 10 ml/kg title comp.; fluoxetine dissolved in saline

Half-life Time (Pharmacological Data)

1.7 - 8.2 h

Results

title comp. elimination half life increased by 4.6 fold in plasma (from 1.8 to 8.2 h) and by 3.4 fold in brain (from 1.7 to 5.8 h); figure; table

Reference

Upreti, Vijay V.; Eddington, Natalie D.

Journal of Pharmaceutical Sciences, 2008 , vol. 97, # 4 p. 1593 - 1605 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

sf9 cell membranes expressing human α2C-adrenoceptors

Concentration (Pharmacological Data)

0.1 - 1 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

radioligand-binding assay; membrane suspension incubated with <3H>yohimbine in presence of title comp. at 25 deg C; Tris-HCl buffer, pH 7.4; washed; filtered; radioactivity on filters determined by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

control: vehicle (distilled water, 1 ml per kg); nonspecific binding determined in presence of phentolamine; pKi = -logKi, Ki in mol/l

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

4.69 dimensionless

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Wistar rat vas deferens membranes

Sex

male

Concentration (Pharmacological Data)

0.1 - 1 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

α1A radioligand-binding assay; membrane suspension incubated with <3H>prazosin in presence of title comp. at 25 deg C; Tris-HCl buffer, pH 7.4; washed; filtered; radioactivity on filters determined by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

control: vehicle (distilled water, 1 ml per kg); nonspecific binding determined in presence of phentolamine; pKi = -logKi, Ki in mol/l

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

4.95 dimensionless

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Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Wistar rat submandibular gland membranes

Sex

male

Concentration (Pharmacological Data)

0.1 - 1 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

α2A radioligand-binding assay; membrane suspension incubated with <3H>yohimbine in presence of title comp. at 25 deg C; Tris-HCl buffer, pH 7.4; washed; filtered; radioactivity on filters determined by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

control: vehicle (distilled water, 1 ml per kg); nonspecific binding determined in presence of phentolamine; pKi = -logKi, Ki in mol/l

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

4.97 dimensionless

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Wistar rat kidney membranes

Sex

male

Concentration (Pharmacological Data)

0.1 - 1 mmol/l

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

α2B radioligand-binding assay; membrane suspension incubated with <3H>yohimbine in presence of title comp. at 25 deg C; Tris-HCl buffer, pH 7.4; washed; filtered; radioactivity on filters determined by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

control: vehicle (distilled water, 1 ml per kg); nonspecific binding determined in presence of phentolamine; pKi = -logKi, Ki in mol/l

Type (Pharmacological Data)

pKi

Value of Type (Pharmacological Data)

5.06 dimensionless

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

chronotropic neg.

Species or Test-

Wistar rat

System (Pharmacological Data)

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Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

radiometric device enabling measurement of heart rate implanted; animals allowed to recover for 7 days; title comp. administered; heart rate observed for 350 min

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. elicited initial bradycardia (figure)

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

muscle relaxant

Species or TestSystem (Pharmacological Data)

Wistar rat vas deferens epididymal portion

Sex

male

Concentration (Pharmacological Data)

1E-07 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

dissolved in distilled water; added cumulatively in 0.5 log unit increments at 5 min intervals

Method (Pharmacological Data)

preparation attached to myograph transducers under 1 g tension in bath at 37 deg C in Krebs-Henseleit solution with nifedipine; placed between electrodes and stimulated; bathing fluid changed; title comp administered; isometric twitch measured

Further Details (Pharmacological Data)

stimulated every 5 min with single stimulus (0.5 ms pulses, supramaximal pulses); pD2 = -logEC50, for EC50 in mol/l

Type (Pharmacological Data)

pD2

Value of Type (Pharmacological Data)

5.46 dimensionless

Results

title comp. reduced size of twitch in concentration-dependent manner (figure)

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

muscle contractive

Species or TestSystem (Pharmacological Data)

Wistar rat vas deferens

Sex

male

Concentration (Pharmacological Data)

Ca. 1E-07 - 3E-05 mol/l

Kind of Dosing

dissolved in distilled water

(Pharmacological Data)

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Method (Pharmacological Data)

preparation attached to myograph transducers under 1 g tension in organ bath at 37 deg C in Krebs-Henseleit solution; after 30 min, tissues contracted with noradrenaline; bathing fluid changed; title comp administered; isometric contractions measured

Results

title comp. produced concentration-dependent increase in contraction (figure)

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

muscle contractive

Species or TestSystem (Pharmacological Data)

Wistar rat thoracic aortic ring

Sex

male

Concentration (Pharmacological Data)

1E-06 - 0.0001 mol/l

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

aortic rings attached to myograph transducers under 1 g tension in organ bath at 37 deg C in Krebs-Henseleit solution; after 30 min, tissues contracted with KCl; bathing fluid changed; title comp administered; isometric contractions measured

Further Details (Pharmacological Data)

after last dose of title comp., tissues exposed to phenylephrine to assess maximum response of vessel

Results

title comp. produced concentration-dependent increase in contraction which reached 41.0 percent of phenylephrine contraction (figure)

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

radiometric device enabling measurement of locomotor activity implanted; animals allowed to recover for 7 days; title comp. administered; locomotor activity observed for 350 min

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. significantly increased locomotor activity (figure), (table)

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

body temperature; effect on

Species or TestSystem

Wistar rat

(Pharmacological Data)

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Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

radiometric device enabling measurement of core body temperature implanted; animals allowed to recover for 7 days; title comp. administered; core body temperature observed for 350 min

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. produced biphasic response consisting of initial hypothermia followed by hyperthermia (figure); minimum temperature (ca. 36.3 deg C) was reached by 50 min and maximum temperature (38.9 deg C) was reached by 180 min

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

hypertensive

Species or TestSystem (Pharmacological Data)

Wistar rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

20 mg/kg

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

radiometric device enabling measurement of blood pressure implanted; animals allowed to recover for 7 days; title comp. administered; systolic, diastolic and mean blood pressure observed for 350 min

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. produced increase in mean blood pressure reaching peak by 40 - 60 min after administration and remained significantly higher than vehicle group up to 300 min (figure, table); systolic and diastolic pressure remained higher for entire period

Reference

Bexis, Sotiria; Docherty, James R.

British Journal of Pharmacology, 2006 , vol. 147, # 8 p. 926 - 934 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

5-hydroxytryptamine uptake; inhibition of

Species or TestSystem (Pharmacological Data)

SK-N-MC cells expressing human serotonin transporter

Concentration (Pharmacological Data)

Ca. 0.1 - 10000 μmol/l

Method (Pharmacological Data)

cells transiently transfected with human serotonin transporter cDNA; 48 h later <3H>5-HT uptake experiments conducted with title comp. in Krebs-Ringer buffer; uptake of <3H>5-HT determined for up to 48 h by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

5-HT: 5-hydroxytryptamine (serotonin); specific <3H>5-HT uptake defined as uptake inhibitable by fluoxetine; Ki determined with 20 nmol/l <3H>5-HT

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Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

107 μmol/l

Results

conc.-dependent inhibition of cellular <3H>5-HT uptake; after 4 h exposure to 100 μmol/l title comp. <3H>5-HT uptake inhibited by ca.

30 percent (diagram)

Reference

Jones, Douglas C.; Lau, Serrine S.; Monks, Terrence J.

Journal of Pharmacology and Experimental Therapeutics, 2004 , vol. 311, # 1 p. 298 - 306 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

5-hydroxytryptamine uptake; inhibition of

Species or TestSystem (Pharmacological Data)

SK-N-MC cells expressing human dopamine transporter

Method (Pharmacological Data)

cells transiently transfected with human dopamine transporter cDNA; 48 h later <3H>5-HT uptake experiments conducted with title comp. in Krebs-Ringer buffer; uptake of <3H>5-HT determined for up to 48 h by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

specific <3H>5-HT uptake defined as uptake inhibitable by fluoxetine

Comment (Pharmacological Data)

No effect

Reference

Jones, Douglas C.; Lau, Serrine S.; Monks, Terrence J.

Journal of Pharmacology and Experimental Therapeutics, 2004 , vol. 311, # 1 p. 298 - 306 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

dopamine uptake stimulant

Species or TestSystem (Pharmacological Data)

SK-N-MC cells expressing human serotonin transporter

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

cells transiently transfected with human serotonin transporter (hSERT) cDNA; 48 h later <3H>dopamine (DA) uptake experiments conducted with title comp. in Krebs-Ringer buffer; uptake of DA determined for up to 48 h by liquid scintillation spectroscopy

Further Details (Pharmacological Data)

further investigations on mechanism of action with fluoxetine and nomifensine

Results

title comp. stimulated uptake of DA, by ca. 3.5-fold over control levels; maximum stimulation between 4 and 8 h (graphs); effect mediated by hSERT (diagram)

Reference

Jones, Douglas C.; Lau, Serrine S.; Monks, Terrence J.

Journal of Pharmacology and Experimental Therapeutics, 2004 , vol. 311, # 1 p. 298 - 306 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

reactive oxygen species generation stimulant

Species or TestSystem (Pharmacological Data)

SK-N-MC cells expressing human serotonin transporter

Concentration (Pharmacological Data)

10 - 400 μmol/l

Method (Pharmacological Data)

cells transiently transfected with human serotonin transporter (hSERT) cDNA; loaded with 2',7'-dichlorofluorescein diacetate, exposed to title comp. for up to 24 h in Krebs-Ringer buffer; ROS generation monitored using microplate fluorescence reader

Further Details (Pharmacological Data)

ROS: reactive oxygen species; further investigations on mechanism of action with fluoxetine and nomifensine

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Results

title comp. induced dose-dependent, rapid ROS generation with maximum at ca. 0.5 h (ca. 30 percent increase at 100 μmol/l), rate of ROS generation declines rapidly after the initial burst; effect requires functional hSERT

Reference

Jones, Douglas C.; Lau, Serrine S.; Monks, Terrence J.

Journal of Pharmacology and Experimental Therapeutics, 2004 , vol. 311, # 1 p. 298 - 306 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

reactive oxygen species generation stimulant

Species or TestSystem (Pharmacological Data)

SK-N-MC cells expressing human dopamine transporter

Concentration (Pharmacological Data)

10 - 400 μmol/l

Method (Pharmacological Data)

cells transiently transfected with human dopamine transporter (hDAT) cDNA; loaded with 2',7'-dichlorofluorescein diacetate, exposed to title comp. for up to 24 h in Krebs-Ringer buffer; ROS generation monitored using microplate fluorescence reader

Further Details (Pharmacological Data)

ROS: reactive oxygen species; further investigations on mechanism of action with fluoxetine and nomifensine

Results

title comp. induced dose-dependent, rapid ROS generation with maximum at ca. 0.5 h (ca. 20 percent increase at 100 μmol/l), rate of ROS generation declines rapidly after the initial burst; effect insensitive to fluoxetine or nomifensine

Reference

Jones, Douglas C.; Lau, Serrine S.; Monks, Terrence J.

Journal of Pharmacology and Experimental Therapeutics, 2004 , vol. 311, # 1 p. 298 - 306 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

COS-7 cells

Concentration (Pharmacological Data)

Ca. 1E-12 - 0.0001 mol/l

Method (Pharmacological Data)

cells transiently expressing h5-HT2B receptors; radioligand displacement assay

Further Details (Pharmacological Data)

Ki values calculated using Cheng-Prusoff approximation; 5-HT: 5-hydroxytryptamine

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

100 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat brain synaptosomes

Method (Pharmacological Data)

rat whole brain minus cerebellum and caudate homogenized; preparation centrifuged; supernatant incubated with 7 nmol/l <3H>NE and RTI-229 (1 h, 25 deg C), then title comp. added (30 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 > 10000 nmol/l; NE: norepinephrine

Type

EC50

(Pharmacological Data)

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Value of Type (Pharmacological Data)

108 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate synaptosomes

Method (Pharmacological Data)

caudate homogenized and centrifuged; supernatant incubated with 5 nmol/l <3H>DA (30 min, 25 deg C), then title comp. added (5 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 > 10000 nmol/l; DA: dopamine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

190 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat brain synaptosomes

Method (Pharmacological Data)

rat whole brain minus cerebellum and caudate homogenized with reserpine, nomifensine and GBR12935 added; preparation centrifuged; supernatant incubated with 5 nmol/l <3H>5-HT (1 h, 25 deg C), then title comp. added (5 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 = 44 nmol/l; GBR12935: (diphenylmethoxy)ethyl-4-(3-phenylpropyl)-piperazine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

160 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mitogenic

Species or TestSystem (Pharmacological Data)

human heart valve interstitial cells

Concentration (Pharmacological Data)

10 μmol/l

Method (Pharmacological

cells incubated with title comp. (15 min), medium collected; immunoblot analysis of Erk 1/2 phosphorylation; total Erk 1/2 measured for comparison

Data)

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Further Details (Pharmacological Data)

vehicle control; reference comp.: 5-hydroxytryptamine (5-HT), 5-HT2B/2C receptor antagonist 5-methyl-1-(3-pyridylcarbamoyl)-1,2,3,5tetrahydropyrrolo<2,3-f>indole (SB206553); Erk: extracellular signal-regulated kinase

Results

title comp. and 5-HT (but not SB206553) induced short-term mitogenic effect (figure)

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mitogenic

Species or TestSystem (Pharmacological Data)

human heart valve interstitial cells

Concentration (Pharmacological Data)

10 μmol/l

Method (Pharmacological Data)

cells incubated with title comp. (3 d) with/without SB206553, 12 h before end of treatment pulsed with <3H>TdR; assay for <3H>TdR incorporation by liquid scintillation counting

Further Details (Pharmacological Data)

vehicle control; reference comp.: 5-hydroxytryptamine (5-HT), 5-HT2B/2C receptor antagonist 5-methyl-1-(3-pyridylcarbamoyl)-1,2,3,5tetrahydropyrrolo<2,3-f>indole (SB206553); TdR: thymidine deoxyribose

Results

title comp., 5-HT and SB206553 induced ca. 2.5-, 2- and 0.5-fold increase of <3H>TdR incorporation over control, resp.; coincubation with SB206553 prevented this effect of title comp. and 5-HT (figure)

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

HEK293 cells

Concentration (Pharmacological Data)

Ca. 1E-12 - 0.0001 mol/l

Method (Pharmacological Data)

stimulation of phosphatidylinositol hydrolysis via h5-HT2B receptors activation determined

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 = 1 nmol/l

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

190 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

uptake; inhibition of

Species or TestSystem (Pharmacological Data)

Wistar rat left ventricular slice

Sex

male

Kind of Dosing

dissolved in distilled water

(Pharmacological Data)

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Method (Pharmacological Data)

slices incubated with title comp. and <3H>noradrenaline (25 nmol/l) for 15 min at 37 deg C; filtered; incubated overnight with 3 percent trichloracetic acid at 4 deg C; <3H>noradrenaline accumulation measured

Further Details (Pharmacological Data)

nonspecific uptake determined by parallel incubation at 4 deg C; reference comp.: cocaine (-log EC50 = 6.16)

Type (Pharmacological Data)

-log EC50

Value of Type (Pharmacological Data)

5.68 dimensionless

Reference

Cleary, Linda; Docherty, James R.

European Journal of Pharmacology, 2003 , vol. 476, # 1-2 p. 31 - 34 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

Wistar rat cerebral cortex membranes

Sex

male

Kind of Dosing (Pharmacological Data)

dissolved in distilled water

Method (Pharmacological Data)

noradrenaline transporter binding study; membranes incubated with title comp. and <3H>nisoxetine for 4 h at 4 deg C; filtered; scintillation cocktail incubated overnight and counted

Further Details (Pharmacological Data)

nonspecific binding determined in presence of desipramine

Type (Pharmacological Data)

-log EC50

Value of Type (Pharmacological Data)

4.66 dimensionless

Reference

Cleary, Linda; Docherty, James R.

European Journal of Pharmacology, 2003 , vol. 476, # 1-2 p. 31 - 34 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

muscle contraction; effect on

Species or TestSystem (Pharmacological Data)

Wistar rat right ventricle

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in distilled water

Method (Pharmacological Data)

ventricular strips were set up between platinum electrodes and isometric force transducer under 2 g tension and paced at frequency of 1 Hz; equilibrated; NA added; tissue exposed to title comp. for 30 min; CRC to NA recorded in presence of title comp.

Further Details (Pharmacological Data)

controls: NA (noradrenaline), vehicle; ref.: cocaine; CRC: concentration-response curve

Results

maximum contractile effect of NA was not significantly affected by title comp. (200/178.9 percent by title comp. and vehicle, respectively); diagram

Reference

Cleary, Linda; Buber, Robert; Docherty, James R.

European Journal of Pharmacology, 2002 , vol. 451, # 3 p. 303 - 308 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

muscle contraction; increase of

Species or TestSystem (Pharmacological Data)

Wistar rat right ventricle

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in distilled water

Method (Pharmacological Data)

ventricular strips were set up between platinum electrodes and isometric force transducer under 2 g tension and paced at a frequency of 1 Hz; equilibrated; NA added; tissue exposed to title comp. for 30 min; contractile potency of NA determined

Further Details (Pharmacological Data)

controls: NA (noradrenaline), vehicle; ref.: cocaine

Type (Pharmacological Data)

pD2

Value of Type (Pharmacological Data)

5.92 dimensionless

Results

title comp. significantly increased the potency of NA as compared to vehicle; table, diagram

Reference

Cleary, Linda; Buber, Robert; Docherty, James R.

European Journal of Pharmacology, 2002 , vol. 451, # 3 p. 303 - 308 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

muscle contraction; decrease of

Species or TestSystem (Pharmacological Data)

Wistar rat right ventricle

Sex

male

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in distilled water

Method (Pharmacological Data)

ventricular strips were set up between platinum electrodes and isometric force transducer under 2 g tension and paced at frequency of 1 Hz; equilibrated; IS added; tissue exposed to title comp. for 30 min; CRC to IS recorded in presence of title comp.

Further Details (Pharmacological Data)

controls: IS (isoprenaline), vehicle; ref.: cocaine; CRC: concentration-response curve

Results

presence of title comp. caused a significantly lower maximum contractile effect to IS as compared to vehicle; diagram

Reference

Cleary, Linda; Buber, Robert; Docherty, James R.

European Journal of Pharmacology, 2002 , vol. 451, # 3 p. 303 - 308 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

muscle contraction; effect on

Species or TestSystem (Pharmacological Data)

Wistar rat right ventricle

Sex

male

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Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in distilled water

Method (Pharmacological Data)

ventricular strips were set up between platinum electrodes and isometric force transducer under 2 g tension and paced at a frequency of 1 Hz; equilibrated; IS added; tissue exposed to title comp. for 30 min; contractile potency of IS determined

Further Details (Pharmacological Data)

controls: IS (isoprenaline), vehicle; ref.: cocaine

Type (Pharmacological Data)

pD2

Value of Type (Pharmacological Data)

7.03 dimensionless

Results

title comp. did not significantly affect the response to IS; table, diagram

Reference

Cleary, Linda; Buber, Robert; Docherty, James R.

European Journal of Pharmacology, 2002 , vol. 451, # 3 p. 303 - 308 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neurotoxicity

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

10 mg/kg

Exposure Period (Pharmacological Data)

7 d

Method (Pharmacological Data)

animals (weights 200-250 g) pretreated with acivicin (18 mg/kg, i.p.) 20 min prior title comp. administration; 12-h light/dark cycle; 72 deg F; neurotransmitter analysis of brain tissues

Results

inhibition of γ-glutamyl transpeptidase; thioether metabolites contribution (diagrams)

Reference

Bai; Jones; Lau; Monks

Chemical Research in Toxicology, 2001 , vol. 14, # 7 p. 863 - 870 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

in vivo (male Sprague-Dawley trained rats) ability to discriminate serotonin-releasing agents and hallucinogens from saline (training drug/ED50, μmol/kg): (+)-amphetamine/no substitution, (+)-MBDB/2.07

Reference

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

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

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

human 5-HT2A receptors

Method (Pharmacological Data)

cells grown, harvested and competition assays performed using <3H>DOB radioligand

Type (Pharmacological Data)

Ki

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Value of Type (Pharmacological Data)

1800 mmol/l

Results

increased affinity for <3H>DOB labeled receptors

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. 412 - 426 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; binding activity

Species or TestSystem (Pharmacological Data)

human 5-HT2A receptors

Method (Pharmacological Data)

cells grown, harvested and competition assays performed using <3H>ketanserin radioligand

Type (Pharmacological Data)

Ki

Value of Type (Pharmacological Data)

4500 nmol/l

Results

modest affinity for <3H>ketanserin labeled receptors

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. 412 - 426 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

central stimulation

Species or TestSystem (Pharmacological Data)

albino ICR mice

Sex

male and female

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 - 10 mg/kg

Kind of Dosing (Pharmacological Data)

1, 3, and 10 mg/kg

Exposure Period (Pharmacological Data)

10 - 40 min

Method (Pharmacological Data)

mouse weight 25-30 g; acclimated for 30 min prior to drug treament; central stimulation assayed by locomotor activity (distance traversed) and by rearing frequency, recorded simultaneously by computerized video tracking and behavior recognition system

Results

significantly increased both locomotor activity and rearing frequency

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. 412 - 426 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

incorporation into hair

Species or TestSystem (Pharmacological Data)

Dark-Agouti rats

Sex

male

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71 of 76

72 of 76

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Exposure Period (Pharmacological Data)

10 d

Method (Pharmacological Data)

rats of 95-105 g, 5 wks old; back hair of rats shaved; hair collected; blood collected 5, 15, 30, 60, 120, 360 min after dosing; plasma prepared; areas under conc. vs. time curve (AUCs) calculated; incorporated rates (ICRs) determination

Results

AUC, 411.3 μg*min/ml; 121.90 ng/mg conc. in hair; ICR, 0.30

Reference

Nakahara, Yuji; Kikura, Ruri

Archives of Toxicology, 1996 , vol. 70, # 12 p. 841 - 849 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

neurotoxicity

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

subcutaneous

Concentration (Pharmacological Data)

93 μmol/kg

Exposure Period (Pharmacological Data)

0.5 - 168 h

Method (Pharmacological Data)

in vivo; 200-225 g rats maintained on 12 h light/dark cycle and with free access to food and water; behavior, weight, and food and water intake were monitored; sacrificed at determined times; brain quickly removed and var. regions were dissected free;

Further Details (Pharmacological Data)

norepinephrine, dopamine, HVA, 5-HT, and 5-HIAA levels determined simultaneously by HPLC-CEAS

Results

drug-treated animals became hyperactive, aggressive, and displayed forepaw treading and Straub tails; caused short-term alterations in dopaminergic, serotonergic, and noradrenergic systems

Reference

Miller, R. Timothy; Lau, Serrine S.; Monks, Terrence J.

Chemical Research in Toxicology, 1996 , vol. 9, # 2 p. 457 - 465 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Accumulation

Species or TestSystem (Pharmacological Data)

human

Sex

male

Method (Pharmacological Data)

chronic drug abuse; sampling head hair and fingernail; hot alkaline hydrolysis; deuterated internal standard; three-step extraction procedure; derivatization by propionylation; GC/MS analysis

Further Details (Pharmacological Data)

22-year old male

Results

concentration: 8.0 ng/mg in hair and 9.7 ng/mg in fingernail

Reference

Cirimele; Kintz; Mangin

Archives of Toxicology, 1995 , vol. 70, # 1 p. 68 - 69 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

AUC

Species or Test-

dark-agouti rat

System (Pharmacological Data)

73 of 76

74 of 76

75 of 76

76 of 76

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

5 mg/kg

Kind of Dosing (Pharmacological Data)

drug administered once a day for 10 successive days

Exposure Period (Pharmacological Data)

10 d

Method (Pharmacological Data)

rats 5 weeks old; back hair shaved before experiment; blood samples collected 5, 15, 30, 60, 120, 360 min after drug administration; newly grown hair samples collected 4 weeks after first drug administration

Further Details (Pharmacological Data)

drug level in plasma and hair determination; GC/MS; HPLC

Type (Pharmacological Data)

AUC

Value of Type (Pharmacological Data)

6.3 μg*min/ml

Results

concentration in hair <H> = 3.16 ng/mg; drug incorporation rate ICR (<H>/AUC) = 0.5

Reference

Nakahara; Takahashi; Kikura

Biological and Pharmaceutical Bulletin, 1995 , vol. 18, # 9 p. 1223 - 1227 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

in vitro the ability to inhibit the accumulation of <3H>serotonin IC50=369 nM, <3H>dopamine IC50=1356 nM and <3H>norepinephrine IC50=629 nM (rats brain)

Reference

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

Journal of Medicinal Chemistry, 1993 , vol. 36, # 23 p. 3700 - 3706 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

binding affinity at 5-HT1C and 5-HT2 serotonin receptors; lack of selectivity

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)

analgetic potency, influence on motor activity (male NMRI-mouse, doses: 100 mg/kg, 20 mg/kg, 10 mg/kg, p.o.); phychotomimetic potency (man and woman, dose 60-120 mg, p.o.)

Reference

Braun; Shulgin

Arzneimittel-Forschung, 1980 , vol. 30, # 5 p. 825 - 830 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

central analgesia activity (mice); central stimulation activity: motor activity (mice), psychotomimetic activity (human)

Reference

Braun; Shulgin

Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details

Other Data Exposure Assessment (2) 1 of 2

Exposure

presence in surface water; Llobregat River, its main tributaries (Cardener River and Anoia River) and Rubi creek in NE Spain; sampling in January, March and May 2007

Sources

human source contaminants

Reference

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc

Environmental Science and Technology, 2008 , vol. 42, # 18 p. 6809 - 6816 Title/Abstract Full Text View citing articles Show Details

2 of 2

Exposure

presence in hair and fingernails; 22-year-old male

Sources

chronic drug abuse

Reference

Cirimele; Kintz; Mangin

Archives of Toxicology, 1995 , vol. 70, # 1 p. 68 - 69 Title/Abstract Full Text View citing articles Show Details

Concentration in the Environment (5) 1 of 5

2 of 5

3 of 5

4 of 5

5 of 5

Media (Concentration in the Environment)

surface water

Location

Llobregat River, NE Spain

Contamination Concentration

0.4 - 15 ng/l

Method, Remarks (Concentration in the Environment)

mean conc.; samples collected once a week every Monday and at the same time (10:00 am) during March 2006 to May 2007 at the intake of a drinking water treatment plant; analyzed by ultraperformance LC-ECI/MS/MS in selected reaction monitoring mode

Reference

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc

Environmental Science and Technology, 2008 , vol. 42, # 18 p. 6809 - 6816 Title/Abstract Full Text View citing articles Show Details

Media (Concentration in the Environment)

surface water

Location

Llobregat River basin, NE Spain

Contamination Concentration

0 - 25 ng/l

Method, Remarks (Concentration in the Environment)

mean conc.; samples collected over 7 consecutive days at the same time (10:00 am) during December 2006 at the intake of a drinking water treatment plant; analyzed by ultraperformance LC-ESI/MS/MS in selected reaction monitoring mode

Reference

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc

Environmental Science and Technology, 2008 , vol. 42, # 18 p. 6809 - 6816 Title/Abstract Full Text View citing articles Show Details

Media (Concentration in the Environment)

surface water

Location

Llobregat River, NE Spain

Contamination Concentration

2 - 50 ng/l

Method, Remarks (Concentration in the Environment)

samples collected during January to June 2007; analyzed by ultraperformance LC-ESI/MS/MS in selected reaction monitoring mode

Reference

Huerta-Fontela, Maria; Galceran, Maria Teresa; Ventura, Francesc

Environmental Science and Technology, 2008 , vol. 42, # 18 p. 6809 - 6816 Title/Abstract Full Text View citing articles Show Details

Media (Concentration in the Environment)

wastewater

Location

Lugano, Switzerland

Contamination Concentration

0 - 0.9 ng/l

Method, Remarks (Concentration in the Environment)

8 water sample collected during 1 week in March 2006 from wastewater treatment plant effluents and influents; HPLC-MS-MS analyzed

Reference

Castiglioni, Sara; Zuccato, Ettore; Crisci, Elisabetta; Chiabrando, Chiara; Fanelli, Roberte; Bagnati, Renzo

Analytical Chemistry, 2006 , vol. 78, # 24 p. 8421 - 8429 Title/Abstract Full Text View citing articles Show Details

Media (Concentration in the Environment)

wastewater

2

Location

Nosedo (Milan), Italy

Contamination Concentration

1.1 - 4.6 ng/l

Method, Remarks (Concentration in the Environment)

8 water sample collected during 1 week in February 2006 from wastewater treatment plant influents and effluents; HPLC-MS-MS analyzed

Reference

Castiglioni, Sara; Zuccato, Ettore; Crisci, Elisabetta; Chiabrando, Chiara; Fanelli, Roberte; Bagnati, Renzo

Analytical Chemistry, 2006 , vol. 78, # 24 p. 8421 - 8429 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 4905684

CAS Registry Number: 4764-17-4, 51497-09-7, 61614-60-6, 6562066-8 Type of Substance: heterocyclic Molecular Formula: C10H13NO2

Linear Structure Formula: C10H13NO2

Molecular Weight: 179.219

InChI Key: NGBBVGZWCFBOGO-UHFFFAOYSA-N

no reactions.

Identification Bioactivity (2)

1

Identification Spectra (1) Bioactivity (13)

14

Synthesize | Hide Details Find similar

Identification Substance Label (1) Label

Reference

20-(-)

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

Bioactivity Pharmacological Data (2) 1 of 2

2 of 2

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

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

Chemical Name: (+)-Tenamfetamine

3

Reaxys Registry Number: 5260330

CAS Registry Number: 65620-66-8 Type of Substance: heterocyclic Molecular Formula: C10H13NO2

Linear Structure Formula: C10H13NO2

Molecular Weight: 179.219

InChI Key: NGBBVGZWCFBOGO-ZETCQYMHSA-N

3 prep out of 5 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-Tenamfetamine, “Sally”, (+)-MDA, (S)-MDA, S-MDA, MDA, (S)-(+)-1-(1,3-benzodioxol-5-yl)-2-propanamine Identification Substance Label (4) Label

Reference

S-MDA

Keizers, Peter H. J.; De Graaf, Chris; De Kanter, Frans J. J.; Oostenbrink, Chris; Feenstra, K. Anton; Commandeur, Jan N. M.; Vermeulen, Nico P. E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 19 p. 6117 - 6127 Title/Abstract Full Text View citing articles Show Details

(S)-7a

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

S-1a: free base

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

(S)-(+)-1

Nichols, David E.; Lloyd, David H.; Hoffman, Andrew J.; Nichols, Maxine B.; Yim, George K. W.

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text View citing articles Show Details

Derivative (1) Derivative

Reference

(S)-(+)-1-(1,3-benzodioxol-5-yl)-2-propanamine hydrochloride

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

Spectra Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

GCMS (Gas chromatography mass spectrometry) Negative chemical ionization Spectrum

Schwaninger, Andrea E.; Meyer, Markus R.; Huestis, Marilyn A.; Maurer, Hans H.

Journal of Mass Spectrometry, 2011 , vol. 46, # 7 p. 603 - 614 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (13) 1 of 13

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols, David E.; Lloyd, David H.; Hoffman, Andrew J.; Nichols, Maxine B.; Yim, George K. W.

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text View citing articles Show Details

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Keizers, Peter H. J.; De Graaf, Chris; De Kanter, Frans J. J.; Oostenbrink, Chris; Feenstra, K. Anton; Commandeur, Jan N. M.; Vermeulen, Nico P. E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 19 p. 6117 - 6127 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

Schwaninger, Andrea E.; Meyer, Markus R.; Huestis, Marilyn A.; Maurer, Hans H.

Journal of Mass Spectrometry, 2011 , vol. 46, # 7 p. 603 - 614 Title/Abstract Full Text View citing articles Show Details

Nash; Roth; Brodkin; Nichols; Gudelsky

Neuroscience Letters, 1994 , vol. 177, # 1-2 p. 111 - 115 Title/Abstract Full Text Show Details

Oberlender; Nichols

Journal of Pharmacology and Experimental Therapeutics, 1990 , vol. 255, # 3 p. 1098 - 1106 Title/Abstract Full Text View citing articles Show Details

Lyon; Glennon; Titeler

Psychopharmacology, 1986 , vol. 88, # 4 p. 525 - 526 Title/Abstract Full Text Show Details

Nichols; Lloyd; Hoffman; Yim

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text Show Details

Steuer, Andrea E.; Schmidhauser, Corina; Schmid, Yasmin; Rickli, Anna; Liechti, Matthias E.; Kraemer, Thomas

Drug Metabolism and Disposition, 2015 , vol. 43, # 12 p. 1864 - 1871 Title/Abstract Full Text View citing articles Show Details

Sandtner, Walter; Stockner, Thomas; Hasenhuetl, Peter S.; Partilla, John S.; Seddik, Amir; Zhang, Yuan-Wei; Cao, Jianjing; Holy, Marion; Steinkellner, Thomas; Rudnick, Gary; Baumann, Michael H.; Ecker, Gerhard F.; Newman, Amy Hauck; Sitte, Harald H.

Molecular Pharmacology, 2016 , vol. 89, # 1 p. 165 - 175 Title/Abstract Full Text View citing articles Show Details

The Board of Trustees of the University of Arkansas; Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US9303092 B2, 2016 ; Title/Abstract Full Text Show Details

2 of 13

3 of 13

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Sandtner, Walter; Stockner, Thomas; Hasenhuetl, Peter S.; Partilla, John S.; Seddik, Amir; Zhang, Yuan-Wei; Cao, Jianjing; Holy, Marion; Steinkellner, Thomas; Rudnick, Gary; Baumann, Michael H.; Ecker, Gerhard F.; Newman, Amy Hauck; Sitte, Harald H.

Molecular Pharmacology, 2016 , vol. 89, # 1 p. 165 - 175 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

The Board of Trustees of the University of Arkansas; Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US9303092 B2, 2016 ; Title/Abstract Full Text Show Details

4 of 13

5 of 13

6 of 13

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Steuer, Andrea E.; Schmidhauser, Corina; Schmid, Yasmin; Rickli, Anna; Liechti, Matthias E.; Kraemer, Thomas

Drug Metabolism and Disposition, 2015 , vol. 43, # 12 p. 1864 - 1871 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; effective concentration (EC); EC50 related to: human TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

6.57 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 Test-

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

System (Pharmacological Data)

7 of 13

8 of 13

9 of 13

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)

1.35 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

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat brain synaptosomes

Method (Pharmacological Data)

rat whole brain minus cerebellum and caudate homogenized; preparation centrifuged; supernatant incubated with 7 nmol/l <3H>NE and RTI-229 (1 h, 25 deg C), then title comp. added (30 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 > 10000 nmol/l; NE: norepinephrine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

50 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

10 of 13

11 of 13

12 of 13

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate synaptosomes

Method (Pharmacological Data)

caudate homogenized and centrifuged; supernatant incubated with 5 nmol/l <3H>DA (30 min, 25 deg C), then title comp. added (5 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 > 10000 nmol/l; DA: dopamine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

98 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat brain synaptosomes

Method (Pharmacological Data)

rat whole brain minus cerebellum and caudate homogenized with reserpine, nomifensine and GBR12935 added; preparation centrifuged; supernatant incubated with 5 nmol/l <3H>5-HT (1 h, 25 deg C), then title comp. added (5 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 = 44 nmol/l; GBR12935: (diphenylmethoxy)ethyl-4-(3-phenylpropyl)-piperazine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

100 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

HEK293 cells

Method (Pharmacological Data)

stimulation of phosphatidylinositol hydrolysis via h5-HT2B receptors activation determined

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50: 1 nmol/l

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

100 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

13 of 13

Comment (Pharmacological Data)

effect on release of <3H>serotonin from rat whole brain synaptosomes in vitro

Reference

Nichols, David E.; Lloyd, David H.; Hoffman, Andrew J.; Nichols, Maxine B.; Yim, George K. W.

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (-)-Tenamfetamine

4

Reaxys Registry Number: 5260331

CAS Registry Number: 4764-17-4, 51497-09-7, 61614-60-6, 6562066-8 Type of Substance: heterocyclic Molecular Formula: C10H13NO2

Linear Structure Formula: C10H13NO2

Molecular Weight: 179.219

InChI Key: NGBBVGZWCFBOGO-SSDOTTSWSA-N

1 prep out of 4 reactions.

Identification Spectra (1) Bioactivity (12)

17

Synthesize | Hide Details Find similar Chemical Names and Synonyms (-)-Tenamfetamine, (-)-MDA, (R)-MDA, R-MDA, MDA, (R)-(-)-1-(1,3-benzodioxol-5-yl)-2-propanamine, (R)-(-)-3,4-(methylenedioxy)amphetamine Identification Substance Label (3) Label

Reference

R-MDA

Keizers, Peter H. J.; De Graaf, Chris; De Kanter, Frans J. J.; Oostenbrink, Chris; Feenstra, K. Anton; Commandeur, Jan N. M.; Vermeulen, Nico P. E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 19 p. 6117 - 6127 Title/Abstract Full Text View citing articles Show Details

R-1a: free base

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

(R)-(-)-1

Nichols, David E.; Lloyd, David H.; Hoffman, Andrew J.; Nichols, Maxine B.; Yim, George K. W.

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text View citing articles Show Details

Spectra Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

GCMS (Gas chromatography mass spectrometry) Negative chemical ionization Spectrum

Schwaninger, Andrea E.; Meyer, Markus R.; Huestis, Marilyn A.; Maurer, Hans H.

Journal of Mass Spectrometry, 2011 , vol. 46, # 7 p. 603 - 614 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (12) 1 of 12

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols, David E.; Lloyd, David H.; Hoffman, Andrew J.; Nichols, Maxine B.; Yim, George K. W.

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text View citing articles Show Details

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Keizers, Peter H. J.; De Graaf, Chris; De Kanter, Frans J. J.; Oostenbrink, Chris; Feenstra, K. Anton; Commandeur, Jan N. M.; Vermeulen, Nico P. E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 19 p. 6117 - 6127 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

Schwaninger, Andrea E.; Meyer, Markus R.; Huestis, Marilyn A.; Maurer, Hans H.

Journal of Mass Spectrometry, 2011 , vol. 46, # 7 p. 603 - 614 Title/Abstract Full Text View citing articles Show Details

Moreno, Daniel; Grenu, Borja Diaz De; Garcia, Begona; Ibeas, Saturnino; Torroba, Tomas

Chemical Communications, 2012 , vol. 48, # 24 p. 2994 - 2996 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

Nash; Roth; Brodkin; Nichols; Gudelsky

Neuroscience Letters, 1994 , vol. 177, # 1-2 p. 111 - 115 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

Oberlender; Nichols

Journal of Pharmacology and Experimental Therapeutics, 1990 , vol. 255, # 3 p. 1098 - 1106 Title/Abstract Full Text View citing articles Show Details

Titeler; Lyon; Glennon

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

Lyon; Glennon; Titeler

Psychopharmacology, 1986 , vol. 88, # 4 p. 525 - 526 Title/Abstract Full Text Show Details

Nichols; Lloyd; Hoffman; Yim

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text Show Details

Steuer, Andrea E.; Schmidhauser, Corina; Schmid, Yasmin; Rickli, Anna; Liechti, Matthias E.; Kraemer, Thomas

Drug Metabolism and Disposition, 2015 , vol. 43, # 12 p. 1864 - 1871 Title/Abstract Full Text View citing articles Show Details

The Board of Trustees of the University of Arkansas; Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US9303092 B2, 2016 ; Title/Abstract Full Text Show Details

2 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

The Board of Trustees of the University of Arkansas; Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip

Patent: US9303092 B2, 2016 ; Title/Abstract Full Text Show Details

3 of 12

4 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Steuer, Andrea E.; Schmidhauser, Corina; Schmid, Yasmin; Rickli, Anna; Liechti, Matthias E.; Kraemer, Thomas

Drug Metabolism and Disposition, 2015 , vol. 43, # 12 p. 1864 - 1871 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; effective concentration (EC); EC50 related to: human TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological

11.73 μmol/l

Data)

5 of 12

6 of 12

7 of 12

8 of 12

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)

2.48 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

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat brain synaptosomes

Method (Pharmacological Data)

rat whole brain minus cerebellum and caudate homogenized; preparation centrifuged; supernatant incubated with 7 nmol/l <3H>NE and RTI-229 (1 h, 25 deg C), then title comp. added (30 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 > 10000 nmol/l; NE: norepinephrine

EC50

Type (Pharmacological Data)

9 of 12

10 of 12

11 of 12

Value of Type (Pharmacological Data)

290 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate synaptosomes

Method (Pharmacological Data)

caudate homogenized and centrifuged; supernatant incubated with 5 nmol/l <3H>DA (30 min, 25 deg C), then title comp. added (5 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 > 10000 nmol/l; DA: dopamine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

900 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat brain synaptosomes

Method (Pharmacological Data)

rat whole brain minus cerebellum and caudate homogenized with reserpine, nomifensine and GBR12935 added; preparation centrifuged; supernatant incubated with 5 nmol/l <3H>5-HT (1 h, 25 deg C), then title comp. added (5 min); liquid scintillation counting

Further Details (Pharmacological Data)

reference comp.: 5-HT (5-hydroxytryptamine), EC50 = 44 nmol/l; GBR12935: (diphenylmethoxy)ethyl-4-(3-phenylpropyl)-piperazine

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

310 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

HEK293 cells

Method (Pharmacological Data)

stimulation of phosphatidylinositol hydrolysis via h5-HT2B receptors activation determined

Further Details

reference comp.: 5-HT (5-hydroxytryptamine), EC50: 1 nmol/l

(Pharmacological Data)

12 of 12

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

150 nmol/l

Reference

Setola, Vincent; Hufeisen, Sandra J.; Grande-Allen, K. Jane; Vesely, Ivan; Glennon, Richard A.; Blough, Bruce; Rothman, Richard B.; Roth, Bryan L.

Molecular Pharmacology, 2003 , vol. 63, # 6 p. 1223 - 1229 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

effect on release of <3H>serotonin from rat whole brain synaptosomes in vitro

Reference

Nichols, David E.; Lloyd, David H.; Hoffman, Andrew J.; Nichols, Maxine B.; Yim, George K. W.

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 530 - 535 Title/Abstract Full Text View citing articles Show Details

Chemical Name: d2-1-(3,4-methylenedioxyphenyl)-2-aminopropane Reaxys Registry Number: 15624542

CAS Registry Number: 1005481-33-3 Molecular Formula: C10H13NO2

Linear Structure Formula: C10H11(2)H2NO2

5

1 prep out of 2 reactions.

1

0 prep out of 2 reactions.

Identification Physical Data (1) Spectra (3)

3

Molecular Weight: 181.203

InChI Key: NGBBVGZWCFBOGO-NCYHJHSESA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms d2-1-(3,4-methylenedioxyphenyl)-2-aminopropane Chemical Name: 3,4-methylenedioxyamphetamine-d5

6

Reaxys Registry Number: 7537470

Type of Substance: heterocyclic Molecular Formula: C10H13NO2

Linear Structure Formula: C10H8D5NO2

Molecular Weight: 184.179

InChI Key: NGBBVGZWCFBOGO-KIUTZQKNSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms 3,4-methylenedioxyamphetamine-d5, 1-methylenedioxyphenyl-2-methylaminopropane-1,2,3,3,3-d5 Identification Substance Label (1) Label

Reference

MDA-D5

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

Physical Data Chromatographic Data (1) Chromatographic data

Reference

LC (Liquid chromatography)

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

Spectra Mass Spectrometry (3) Description (Mass Spectrometry)

Reference

tandem mass spectrometry electrospray ionisation (ESI) high resolution mass spectrometry (HRMS) spectrum

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

electrospray ionisation (ESI) high resolution mass spectrometry (HRMS) spectrum

Fedorova, Ganna; Randak, Tomas; Lindberg, Richard H.; Grabic, Roman

Rapid Communications in Mass Spectrometry, 2013 , vol. 27, # 15 p. 1751 - 1762 Title/Abstract Full Text View citing articles Show Details

TOFMS (Time of flight mass spectrum) ESI (Electrospray ionisation) Spectrum

Bijlsma, Lubertus; Sancho, Juan V.; Hernandez, Felix; Niessen, Wilfried M.A.

Journal of Mass Spectrometry, 2011 , vol. 46, # 9 p. 865 - 875 Title/Abstract Full Text View citing articles Show Details

Chemical Name: DL-[13C6]-3,4-methylenedioxyamphetamine

0 prep out of 2 reactions.

Identification

2

0 prep out of 15 reactions.

Identification Physical Data (4) Spectra (3) Bioactivity (6)

20

Reaxys Registry Number: 26969018

CAS Registry Number: 1419917-29-5 Molecular Formula: C10H13NO2

Linear Structure Formula: C4(13)C6H13NO2

Molecular Weight: 185.153

InChI Key: NGBBVGZWCFBOGO-GBDAEYFOSA-N

7

Synthesize | Hide Details Find similar Chemical Names and Synonyms DL-[13C6]-3,4-methylenedioxyamphetamine, DL-[13C6]-3,4-methylenedioxyamphetamine Identification Substance Label (1) Label

Reference

3a

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (+/-)-Tenamfetamine hydrochloride

8

Reaxys Registry Number: 3916706

CAS Registry Number: 6292-91-7 Type of Substance: heterocyclic Molecular Formula: C10H13NO2*ClH Linear Structure Formula: C10H13NO2*HCl Molecular Weight: 215.68

InChI Key: XLAOKZDOZHZWBK-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+/-)-Tenamfetamine hydrochloride, (+/-)-3,4-methylenedioxyamphetamine hydrochloride, 3,4-methylenedioxyamphetamine hydrochloride, methylenedioxyamphetamine hydrochloride, (d,l)-3,4-methylenedioxyamphetamine, 2-benzo[1,3]dioxol-5-yl-1-methyl-ethylamine; hydrochloride, 2Benzo[1,3]dioxol-5-yl-1-methyl-aethylamin; Hydrochlorid Identification Substance Label (3) Label

Reference

MDA

Wu, Dafang; Victoria Otton, S.; Inaba, Tadanobu; Kalow, Werner; Sellers, Edward M.

Biochemical Pharmacology, 1997 , vol. 53, # 11 p. 1605 - 1612 Title/Abstract Full Text View citing articles Show Details

Carvalho, Marcia; Hawksworth, Gabrielle; Milhazes, Nuno; Borges, Fernanda; Monks, Terrence J.; Fernandes, Eduarda; Carvalho, Felix; Bastos, Maria

Archives of Toxicology, 2002 , vol. 76, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details

Molnr, Borbla; Fodor, Blanka; Boldizsr, Imre; Molnr-Perl, Ibolya

Analytical Chemistry, 2015 , vol. 87, # 20 p. 10188 - 10192 Title/Abstract Full Text View citing articles Show Details

4

DADE BEHRING INC.

Patent: WO2005/58864 A1, 2005 ; Title/Abstract Full Text Show Details

MDA*HCl

Reviriego, Felipe; Navarro, Pilar; Domenech, Antonio; Garcia-Espana, Enrique

Journal of the Chemical Society, Perkin Transactions 2, 2002 , # 9 p. 1634 - 1638 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (3) Related Markush Structure (RN)

Location in Patent

Reference

11337200

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

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

19845725; 19845726

DADE BEHRING INC.

Patent: WO2005/58864 A1, 2005 ;

Title/Abstract Full Text Show Details

Hosick; Thomas A.

Patent: US4120976 A1, 1978 ;

Claim

Title/Abstract Full Text Show Details

Physical Data Melting Point (4) Melting Point

Solvent (Melting Point)

Reference

191 - 192 °C

Benington et al.

Journal of Organic Chemistry, 1958 , vol. 23, p. 1979,1980

Full Text Show Details

188 °C

ethanol

Bruckner

Justus Liebigs Annalen der Chemie, 1935 , vol. 518, p. 226,241 Full Text View citing articles Show Details

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427 Full Text Show Details

188 °C

ethanol diethyl ether

Bruckner

Justus Liebigs Annalen der Chemie, 1935 , vol. 518, p. 226,241 Full Text View citing articles Show Details

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427 Full Text Show Details

180 - 181 °C

Mannich; Jacobsohn

Chemische Berichte, 1910 , vol. 43, p. 193 Full Text View citing articles Show Details

Spectra NMR Spectroscopy (3) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Chemical shifts

1H

CDCl3 various solvent(s)

Reference De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes

Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 1246 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

CDCl3 various solvent(s)

De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes

Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 1246 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H. Solvent(s): further solvent(s)

De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes

Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 1246 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

Reference

Hosick; Thomas A.

Patent: US4120976 A1, 1978 ; Title/Abstract Full Text 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

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

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

Rosenmund

Patent: DE320480 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 13, p. 883 Full Text Show Details

Bruckner

Justus Liebigs Annalen der Chemie, 1935 , vol. 518, p. 226,241 Full Text View citing articles Show Details

Mannich; Jacobsohn

Chemische Berichte, 1910 , vol. 43, p. 193 Full Text View citing articles Show Details

Ide; Buck

Journal of the American Chemical Society, 1940 , vol. 62, p. 425,427

Full Text Show Details

Benington et al.

Journal of Organic Chemistry, 1958 , vol. 23, p. 1979,1980 Full Text Show Details

Kienzle; Bounameaux; Minder; Muggli

Helvetica Chimica Acta, 1986 , vol. 69, # 7 p. 1671 - 1680 Title/Abstract Full Text View citing articles Show Details

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Braun; Shulgin

Journal of Pharmaceutical Sciences, 1980 , vol. 69, # 2 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details

De Boer; Tan; Gorter; Van de Wal; Kettenes-van den Bosch; De Bruijn; Maes

Journal of Mass Spectrometry, 1997 , vol. 32, # 11 p. 1236 - 1246 Title/Abstract Full Text View citing articles Show Details

Reviriego, Felipe; Navarro, Pilar; Domenech, Antonio; Garcia-Espana, Enrique

Journal of the Chemical Society, Perkin Transactions 2, 2002 , # 9 p. 1634 - 1638 Title/Abstract Full Text View citing articles Show Details

Wu, Dafang; Victoria Otton, S.; Inaba, Tadanobu; Kalow, Werner; Sellers, Edward M.

Biochemical Pharmacology, 1997 , vol. 53, # 11 p. 1605 - 1612 Title/Abstract Full Text View citing articles Show Details

Carvalho, Marcia; Hawksworth, Gabrielle; Milhazes, Nuno; Borges, Fernanda; Monks, Terrence J.; Fernandes, Eduarda; Carvalho, Felix; Bastos, Maria

Archives of Toxicology, 2002 , vol. 76, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details

DADE BEHRING INC.

Patent: WO2005/58864 A1, 2005 ; Title/Abstract Full Text Show Details

Type: Review, Lab: EFF_071212, Owner: EFFECT, Number: 000, Revision: 07.12.2012 00:00:00 2012 Full Text Show Details

Zhu, Binling; Meng, Liang; Zheng, Kefang

Forensic Science International, 2014 , vol. 242, p. e44 - e47 Title/Abstract Full Text View citing articles Show Details

Molnr, Borbla; Fodor, Blanka; Boldizsr, Imre; Molnr-Perl, Ibolya

Analytical Chemistry, 2015 , vol. 87, # 20 p. 10188 - 10192 Title/Abstract Full Text View citing articles Show Details

Argente-García; Jornet-Martínez; Herráez-Hernández; Campíns-Falcó

Analytica Chimica Acta, 2016 , vol. 943, p. 123 - 130 Title/Abstract Full Text Show Details

2 of 6

Effect (Pharmacological Data)

locomotor behaviors; effect on

Species or TestSystem (Pharmacological Data)

DAT-KO mouse

Sex

male and female

Method (Pharmacological Data)

Experimental We report here that the pharmacologic inhibition of the rate-limiting enzyme of DA synthesis, TH, almost immediately depletes brain DA to undetectable levels in DAT-KO mice and induces a transient recapitulation of essentially all PD symptoms for up to 16 h. DA-deficient DAT-KO mice (DDD mice) thus represent an acute PD model that is useful for studying the efficacy of compounds that potentially can restore control of locomotion in the absence of any contribution of the dopaminergic system. By using this approach, we found that several amphetamine derivatives can counteract the behavioral manifestations of severe DA deficiency, suggesting that, in addition to well-known DA-mediated effects, amphetamine-like compounds can also affect motor functions in a DA- and DAT-independent manner. Materials and Methods Animals. DAT-KO mice were generated as previously described [11]. Animal care was in accordance with the Guide for Care and Use of Laboratory Animals (National Institutes of Health publication No.865-23, Bethesda, Md., United States) with an approved protocol from the Duke University Institutional Animal Care and Use Committee. C57BL/6J3129Sv/J hybrid WT and DAT-KO mice, 3-5 mo old, of both sexes were used. None of animals used in these studies had the neurodegenerative phenotype sporadically observed in DAT-KO mice [60]. Drugs. Drugs or saline (0.9percent NaCl) were administered intraperitoneally (IP) or subcutaneously (SC) in a volume of 10 ml/kg. The drags were either from Sigma (St. Louis, Mo., United States) or supplied by the National Institute of Drug Abuse (NIDA).

Drugs provided by the NIDA Drug Supply Program included: (+/-)-MDMA, (+)-MDMA, (+/-)-6-OH-MDA, (+/-)-MDA, (+/-)-MDE, (+)-MDE, ()-MDE, and AFT (alpha-ethyl-tryptamine acetate). Neurochemical assessments. Striatal tissue contents of DA and frontal cortical tissue levels of NE were assessed using HPLC-EC (high performance liquid chromatography with electrochemical detection) as described [8]. In vivo microdialysis measurements of striatal extracellular DA levels in freely moving mice were performed at least 24 h after implantation of a microdialysis probe as described previously [50]. Dialysate samples were assayed for DA using HPLC-EC. Behavioral methods. Locomotor activity of littermate WT and DATKO mice was measured in an Omnitech CCDigiscan (Accuscan Instruments, Columbus, Ohio United States) activity monitor under bright illumination [83]. All behavioral experiments were performed between 10:00 AM and 5:00 PM. Activity was measured at 5-min intervals, To evaluate the effects of drugs on motor behaviors, mice were placed into activity monitor chambers (20.x.20 cm) for 30 min and then treated with αMT (250 mg/kg IP). A drug or combination of drugs were injected 1 h after αMT administration, and various parameters of locomotor activity were monitored for up to 3 h. In cumulative dosing experiments, animals were treated with increasing doses of drugs after a 1-h interval. For the akinesia test, the mouse is held by the tail so that it is standing on forelimbs only and moving on its own. The number of steps taken with both forelimbs was recorded during a 30-s trial [57]. The presence of catalepsy was determined and measured by placing the animal's forepaws on a horizontal wooden bar (0.7 cm in diameter), 4 cm above the tabletop. The time until the mouse removed both forepaws from the bar was recorded, with a maximum cut-off time of 3 min [53]. In the grasping test of muscular rigidity, the mouse is suspended by its forelimbs on a metal rod (diameter: 0.25 cm) positioned approximately 20 cm above the table. The time the animal remains on the rod (maximum 1 min) was noted [58]. To assess rigidity in a bracing task, the number of steps taken with each forelimb when the mouse is pushed sideways over a distance of 50 cm was recorded [57]. Tremor was scored visually in mice using the rating scale [54]: 0, no tremor; 1, occasional isolated twi

Results

Akinesia test: ~10-30 number of steps; at Catalepsy test: ~10-170sec; at Grasping test: ~2-10 seconds time spent on the rod of the title compound administered after 1h of αMT treatment; figure is given

Location

Page/Page column 3; 12-15; sheet 9

Reference

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

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

3 of 6

4 of 6

5 of 6

Effect (Pharmacological Data)

nephrotoxic

Species or TestSystem (Pharmacological Data)

human renal proximal tubular cells

Concentration (Pharmacological Data)

100 - 800 μmol/l

Method (Pharmacological Data)

cells isolated from renal cortex tissue by collagenase enzymatic digestion, filtration and density centrifugation; cell monolayer incub. for 24 h with title comp.; cell viability determ. by MTT assay

Further Details (Pharmacological Data)

cell viability > 85 percent; MTT=3-(4,5-dimethyl-1,3-thiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide; in MTT assay cells incubated at 37 deg C in humidified atmosphere cont. 5 percent CO2 for 4 h with MTT, then absorbance measured at 540 nm

Comment (Pharmacological Data)

No effect

Reference

Carvalho, Marcia; Hawksworth, Gabrielle; Milhazes, Nuno; Borges, Fernanda; Monks, Terrence J.; Fernandes, Eduarda; Carvalho, Felix; Bastos, Maria

Archives of Toxicology, 2002 , vol. 76, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

nephrotoxic

Species or TestSystem (Pharmacological Data)

Wistar rat renal proximal tubular cells

Sex

male

Concentration (Pharmacological Data)

100 - 800 μmol/l

Method (Pharmacological Data)

cells isolated from renal cortex tissue by collagenase enzymatic digestion, filtration and density centrifugation; cell monolayer incub. for 24 h with title comp.; cell viability determ. by MTT assay

Further Details (Pharmacological Data)

cell viability > 85 percent; rats maintain. on 12 h day/night; MTT=3-(4,5-dimethyl-1,3-thiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide; in MTT assay cells incubated at 37 deg C in humid. atmosphere cont. 5 percent CO2 for 4 h with MTT, absorbance measured at 540 nm

Comment (Pharmacological Data)

No effect

Reference

Carvalho, Marcia; Hawksworth, Gabrielle; Milhazes, Nuno; Borges, Fernanda; Monks, Terrence J.; Fernandes, Eduarda; Carvalho, Felix; Bastos, Maria

Archives of Toxicology, 2002 , vol. 76, # 10 p. 581 - 588 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; inhib. of

Species or TestSystem (Pharmacological Data)

human liver microsomes

Method (Pharmacological Data)

effect on activity of enzyme CYP2D6 studied; 0.5 to 5.0 μmol/l dextromethorphan incubated in 0.2 mol/l phosphate buffer with (μmol/l): 0.1 NADP, 1 glucose-6-phosphate, 0.5 MgCl2 and 0.2 U glucose-6-phosphate dehydrogenase with/without title compound

Further Details (Pharmacological Data)

reaction started by adding microsomal protein; incubation at 37 deg C for 30 min; stopped with 70 percent perchloric acid; centrifuged; supernatant assayed for dextrorphan by HPLC

Results

competitive inhibitory effect; apparent inhibition constant (Ki) = 1.8 μmol/l

6 of 6

Reference

Wu, Dafang; Victoria Otton, S.; Inaba, Tadanobu; Kalow, Werner; Sellers, Edward M.

Biochemical Pharmacology, 1997 , vol. 53, # 11 p. 1605 - 1612 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

psychotropic activity in male Sprague-Dawley rats

Reference

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (S)-(+)-1-(1,3-benzodioxol-5-yl)-2-propanamine hydrochloride Reaxys Registry Number: 6577773

Type of Substance: heterocyclic Molecular Formula: C10H13NO2*ClH Linear Structure Formula: C10H13NO2*ClH Molecular Weight: 215.68

InChI Key: XLAOKZDOZHZWBK-FJXQXJEOSA-N

2 prep out of 2 reactions.

Identification Physical Data (9) Spectra (2) Bioactivity (3)

4

9

Synthesize | Hide Details Find similar Chemical Names and Synonyms (S)-(+)-1-(1,3-benzodioxol-5-yl)-2-propanamine hydrochloride, (S)-3,4-Methylenedioxyamphetamine hydrochloride, 3,4methylenedioxymethamphetamine hydrochloride Identification Substance Label (4) Label

Reference

MDMA

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

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

(S)MDA*HCl

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

(S)-7a*HCl

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

S-1a*HCl

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (2) Melting Point

Reference

198 °C

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

200 - 202 °C

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Density (1) Measurement

Type

Density 1.284 g·cm-3

Reference

Temperature

(Density)

-60.15 °C

crystallographic

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 1130 Title/Abstract Full Text View citing articles Show Details

Crystal Phase (1) Description (Crystal Phase)

Temperature (Crystal Phase)

Crystal structure determination

-60.15 °C

Reference Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 1130 Title/Abstract Full Text View citing articles Show Details

Crystal System (1) Crystal System

Reference

rhombic

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Interatomic Distances and Angles (1) Description

Comment (Interatomic Distances and Angles)

Interatomic distances and angles

Method of determination: Single crystal X-ray diffraction

Reference Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Optical Rotatory Power (2) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

1.40 g/100ml

H2O

26.6 deg

589 nm

20 °C

[alpha]

2 g/100ml

H2O

26.52 deg

589 nm

Reference Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Space Group (1) Space Group

Reference

18

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Chemical shifts

1H

CDCl3

Comment (NMR Spectroscopy)

Reference Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 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

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Effenberger, Franz; Jaeger, Juergen

Chemistry - A European Journal, 1997 , vol. 3, # 8 p. 1370 - 1374 Title/Abstract Full Text View citing articles Show Details

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

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

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

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

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

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

Comment (Pharmacological Data)

psychotropic activity in male Sprague-Dawley rats

Reference

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (R)-(-)-1-(1,3-benzodioxol-5-yl)-2-propanamine hydrochloride Reaxys Registry Number: 6577774

Type of Substance: heterocyclic Molecular Formula: C10H13NO2*ClH Linear Structure Formula: C10H13NO2*ClH Molecular Weight: 215.68

InChI Key: XLAOKZDOZHZWBK-OGFXRTJISA-N

1 prep out of 1 reactions.

10

Synthesize | Hide Details Find similar Chemical Names and Synonyms (R)-(-)-1-(1,3-benzodioxol-5-yl)-2-propanamine hydrochloride, (R)-3,4-Methylenedioxyamphetamine hydrochloride Identification Substance Label (2) Label

Reference

(R)-MDA*HCl

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Identification Physical Data (7) Spectra (2) Bioactivity (2)

2

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

R-1a*HCl

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

200 - 202 °C

ethanol diethyl ether

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Density (1) Density

Measurement Temperature

Type (Density)

1.285 g·cm-3

-60.15 °C

crystallographic

Reference Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 1130 Title/Abstract Full Text View citing articles Show Details

Crystal Phase (1) Description (Crystal Phase)

Temperature (Crystal Phase)

Crystal structure determination

-60.15 °C

Reference Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 1130 Title/Abstract Full Text View citing articles Show Details

Crystal System (1) Crystal System

Reference

rhombic

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Interatomic Distances and Angles (1) Description

Comment (Interatomic Distances and Angles)

Interatomic distances and angles

Method of determination: Single crystal X-ray diffraction

Reference Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 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)

[alpha]

2 g/100ml

H2O

-25.7 deg

589 nm

Reference Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Space Group (1) Space Group

Reference

18

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Chemical shifts

1H

dimethylsulfoxide-d6

Spin-spin coupling constants

dimethylsulfoxide-d6

Comment (NMR Spectroscopy)

Reference Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

1H-1H

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (2) 1 of 2

2 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Buechler, Jochen; Maichle-Moessmer, Caecilia; Kovar, Karl-Artur

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2000 , vol. 55, # 12 p. 1124 - 1130 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

psychotropic activity in male Sprague-Dawley rats

Reference

Nichols; Hoffman; Oberlender; Jacob III; Shulgin

Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 2009 - 2015 Title/Abstract Full Text View citing articles Show Details

Chemical Name: DL-[13C6]-MDA hydrochloride Reaxys Registry Number: 26969015

CAS Registry Number: 1536075-11-2 Molecular Formula: C10H13NO2*ClH Linear Structure Formula: C4(13)C6H13NO2*ClH

9 prep out of 9 reactions.

Molecular Weight: 221.614

InChI Key: XLAOKZDOZHZWBK-ZHBCWNGOSA-N

11

Synthesize | Hide Details Find similar Chemical Names and Synonyms DL-[13C6]-MDA hydrochloride, DL-[13C6]-3,4-methylenedioxyamphetamine hydrochloride, DL-[13C6]-3,4-methylenedioxyamphetamine hydrochloride

Identification Substance Label (1) Label

Reference

3a

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (1)

Identification Physical Data (2) Spectra (4)

3

Location in Patent

Reference

Page/Page column

CHIRON A/S; Johansen, Jon Eigill; Liu, Huiling; Karlsen, Morten

Patent: US2014/227792 A1, 2014 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

181.1 - 181.6 °C

acetonitrile

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

white

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

1H

dimethylsulfoxide-d6

400 MHz

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

dimethylsulfoxide-d6

100 MHz

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

Reference

Mass Spectrometry (2) Description (Mass Spectrometry)

Reference

electron impact (EI) spectrum

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details

high resolution mass spectrometry (HRMS) spectrum

Karlsen, Morten; Liu, Huiling; Berg, Thomas; Johansen, Jon Eigill; Hoff, Bard Helge

Journal of Labelled Compounds and Radiopharmaceuticals, 2014 , vol. 57, # 5 p. 378 - 387 Title/Abstract Full Text View citing articles Show Details