3-Methyl-2-phenylmorpholine (Phenmetrazine) by Asch

Reaxys

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Reactions (99)

Substances (17)

Structure

Citations (132)

Structure/Compound Data Chemical Name: phenmetrazine Reaxys Registry Number: 140490

CAS Registry Number: 134-49-6 Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N

N° of preparations All Preps | All Reactions 9 prep out of 27 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms phenmetrazine, Phenmetrazine, A 66, 2-phenyl-3-methyl-morpholine, 2-methyl-3-phenylmorpholine, Phenmetrazin, 3-methyl-2-phenyl-morpholine Identification Substance Label (18) Label

Reference

Yordanova; Dantchev; Shvedov; Karanov

Archiv der Pharmazie, 1990 , vol. 323, # 1 p. 41 - 42 Title/Abstract Full Text View citing articles Show Details

Marciniec

Pharmazie, 1985 , vol. 40, # 1 p. 30 - 33 Title/Abstract Full Text View citing articles Show Details

Kuhnert-Brandstaetter et al.

Available Data

N° of ref.

Identification Physical Data (24) Spectra (10) Bioactivity (9) Other Data (17)

107

Pharmaceutica Acta Helvetiae, 1975 , vol. 50, p. 360,364 Full Text Show Details

Coutts,R.T. et al.

Biomedical Mass Spectrometry, 1975 , vol. 2, p. 137 - 141 Full Text View citing articles Show Details

Maurich; Rubessa

Bollettino Chimico Farmaceutico, 1973 , vol. 112, # 7 p. 465 - 471 Title/Abstract Full Text View citing articles Show Details

trans 2

Spassov; Stefanovsky; Kurtev; Fodor

Chemische Berichte, 1972 , vol. 105, # 8 p. 2467 - 2475 Title/Abstract Full Text View citing articles Show Details

cis-2

Spassov; Stefanovsky; Kurtev; Fodor

Chemische Berichte, 1972 , vol. 105, # 8 p. 2467 - 2475 Title/Abstract Full Text View citing articles Show Details

Portoghese

Journal of Medicinal Chemistry, 1967 , vol. 10, p. 1057 Full Text View citing articles Show Details

III

Portoghese

Journal of Medicinal Chemistry, 1967 , vol. 10, p. 1057 Full Text View citing articles Show Details

673

Hayden et al.

Journal - Association of Official Analytical Chemists, 1966 , vol. 49, p. 1109,1119 Full Text Show Details

FRENCH; TRUELOVE

Journal of pharmaceutical sciences, 1965 , vol. 54, p. 306 - 308 Title/Abstract Full Text Show Details

Kuhnert-Brandstaetter et al.

Scientia Pharmaceutica, 1964 , vol. 32, p. 308,310,320 Full Text Show Details

468

Brannon; Hayden

Journal - Association of Official Analytical Chemists, 1964 , vol. 47, p. 918,962 Full Text Show Details

Klosa,J.

Journal fuer Praktische Chemie (Leipzig), 1963 , vol. 21, p. 12 - 17 Full Text View citing articles Show Details

Searle

Patent: US3074941 , 1961 ; Chem.Abstr., 1963 , vol. 59, # 10069c Full Text Show Details

Chem,Fabrik Ravensberg GmbH,

Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

Chem,Fabrik Ravensberg GmbH,

Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

Ravensberg GmbH

Patent: GB816576 , 1955 ; Chem.Abstr., 1960 , # 1564 Full Text Show Details

Patent-Specific Data (3) Prophetic Compound

Related Markush Structure (RN) 22041163; 22041164

Location in Patent

Reference RESEARCH TRIANGLE INSTITUTE; UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, C/O NATIONAL INSTITUTES OF HEALTH, OFFICE OF TECHNOLOGY TRANSFER; BLOUGH, Bruce E.; ROTHMAN, Richard; LANDAVAZO, Antonio; PAGE, Kevin M.;

DECKER, Ann Marie

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Claim

Pharmaquest Ltd.

Patent: US6217904 B1, 2001 ; Title/Abstract Full Text Show Details

Keown; Wendy J.; Ford; Betty J.; Stoddard; Sandra L.

Patent: US5543405 A1, 1996 ; Title/Abstract Full Text Show Details

Interneuron Pharmaceuticals, Inc.

Patent: US5096712 A1, 1992 ; Title/Abstract Full Text Show Details

Battey, Alyce S.; Battey, Jacob

Patent: US2002/22057 A1, 2002 ; Title/Abstract Full Text Show Details

Finke, Paul E.; Mills, Sander G.; Plummer, Christopher W.; Shah, Shrenik K.; Truong, Quang T.

Patent: US2003/114495 A1, 2003 ; Title/Abstract Full Text Show Details

The Procter and Gamble Company

Patent: US4557934 A1, 1985 ; Title/Abstract Full Text Show Details

Interneuron Pharmaceuticals, Inc.

Patent: US5019594 A1, 1991 ; Title/Abstract Full Text Show Details

Waleh, Nahid S.; Kilduff, Thomas S.

Patent: US2002/166135 A1, 2002 ; Title/Abstract Full Text Show Details

prophetic product

Claim

Cooper; Irving

Patent: US4255439 A1, 1981 ; Title/Abstract Full Text Show Details

Derivative (10) Derivative

Comment (Derivative)

Reference

HCl-salt: F 174-177grad; >=150grad subl.; F(Mod II) 172-175grad; Eutektische Temperatur mit: a) Benzanilid: 112grad , b) mit Racephedrin*HCl: 140grad ;Pikrat: F 198-202grad; Pikrolonat: F 238-243grad; Styphnat: F 238-242grad ; Diliturat(Hydrat): F 26

Kuhnert-Brandstaetter et al.

Pharmaceutica Acta Helvetiae, 1975 , vol. 50, p. 360,364 Full Text Show Details

Hydrochlorid C11H15NO*HCl: Duennschichtchromatograph. Verh. u. Nachweisreaktionen

Palitzsch et al.

Pharmazie, 1968 , vol. 23, p. 246,248 Full Text Show Details

Cyclohexylsulfamidsaeure-Salz C11H15NO*C6H13NO3S : B : aus 3-Methyl-2-phenyl-morpholin, Cyclosulfamidsaeure/Aceton oder Methanol; F: 142grad<aus Ethanol + Diethylether>

Sciortino

Bollettino Chimico Farmaceutico, 1966 , vol. 105, p. 223,224 Full Text Show Details

Hydrochlorid: F: 174-177gradC; subl. >150gradC

Kuhnert-Brandstaetter et al.

Scientia Pharmaceutica, 1964 , vol. 32, p. 308,310,320 Full Text Show Details

Pikrat: F: 198-202gradC

Kuhnert-Brandstaetter et al.

Scientia Pharmaceutica, 1964 , vol. 32, p. 308,310,320 Full Text Show Details

Hydrochlorid: F : 176 - 178grad

SINSHEIMER; SMITH

Journal of pharmaceutical sciences, 1963 , vol. 52, p. 1080 - 1085 Title/Abstract Full Text Show Details

Hydrochlorid: Amperometrische Bestimmung

Smith et al.

Analytical Chemistry, 1963 , vol. 35, p. 58,60 Full Text Show Details

Tetraphenylborat: F : 149 - 150.5grad(Zers.); IR-Sp.; UV-Max (S.1083)

SINSHEIMER; SMITH

Journal of pharmaceutical sciences, 1963 , vol. 52, p. 1080 - 1085 Title/Abstract Full Text Show Details

Klosa,J.

Journal fuer Praktische Chemie (Leipzig), 1963 , vol. 21, p. 12 17 Full Text View citing articles Show Details

phenmetrazine hydrochloride

Chem,Fabrik Ravensberg GmbH,

Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

HCl-Salz;F:181grad ; 8Chlor-theophyllin-Salz;F: 128

Physical Data Melting Point (2) Melting Point

Reference

178 °C

Kolb; Patt

Arzneimittel-Forschung, 1965 , vol. 15, # 8 p. 924 - 927 Title/Abstract Full Text View citing articles Show Details

175 - 177 °C

Egyesult Gyogyszer es Tapszergyar

Patent: HU149550 , 1960 ; Chem.Abstr., 1963 , vol. 58, # 4582d Full Text Show Details

Boiling Point (5) Boiling Point

Pressure (Boiling Point)

Reference

98 - 105 °C

2.5 Torr

Yordanova; Dantchev; Shvedov; Karanov

Archiv der Pharmazie, 1990 , vol. 323, # 1 p. 41 - 42 Title/Abstract Full Text View citing articles Show Details

142 - 143 °C

15 Torr

Danchev; Stoeva-Tordanova

Farmatsiya (Sofia, Bulgaria), 1972 , vol. 22, # 2 p. 1,3 Chem.Abstr., 1972 , vol. 77, # 101491f Full Text Show Details

Spassov; Stefanovsky; Kurtev; Fodor

Chemische Berichte, 1972 , vol. 105, # 8 p. 2467 - 2475 Title/Abstract Full Text View citing articles Show Details

118 °C

138 - 140 °C

12 Torr

Klosa,J.

Journal fuer Praktische Chemie (Leipzig), 1963 , vol. 21, p. 12 - 17 Full Text View citing articles Show Details

Shozokitagawa

Patent: JP623579 , 1962 ; Chem.Abstr., 1963 , vol. 58, # 9092h Full Text Show Details

142 - 143 °C

Chromatographic Data (1) Chromatographic data

Reference

LC (Liquid chromatography)

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

Dissociation Exponent (2) Comment (Dissociation Exponent)

Reference

(pk')pKa

Beckett; Salami

The Journal of pharmacy and pharmacology, 1972 , vol. 24, # 11 p. 900 - 902 Title/Abstract Full Text View citing articles Show Details

(pk)pK(1)0 : 7.955, bei 25gradin W. (potentiometrisch)

Halmekoski; Lukkari

Suomen Kemistilehti B, 1964 , vol. 37, p. 183 Full Text Show Details

Electrochemical Behaviour (2) Description (Electrochemical Behaviour)

Reference

Electrolytic dissociation / protonation equilibrium

Rucker; Mrongovius; Neugebauer

Archiv der Pharmazie, 1982 , vol. 315, # 10 p. 839 - 846 Title/Abstract Full Text View citing articles Show Details

Electrochemical properties

Reisch; Alfes; Moellmann

Die Pharmazie, 1968 , vol. 23, # 5 p. 245 - 246 Title/Abstract Full Text View citing articles Show Details

Further Information (10) Description (Further Information)

Reference

Further information

Coutts,R.T. et al.

Biomedical Mass Spectrometry, 1975 , vol. 2, p. 137 - 141 Full Text View citing articles Show Details

Further information

Kuhnert-Brandstaetter et al.

Pharmaceutica Acta Helvetiae, 1975 , vol. 50, p. 360,364 Full Text Show Details

Further information

Palitzsch et al.

Pharmazie, 1968 , vol. 23, p. 246,248 Full Text Show Details

Further information

Portoghese

Journal of Medicinal Chemistry, 1967 , vol. 10, p. 1057 Full Text View citing articles Show Details

Further information

Sciortino

Bollettino Chimico Farmaceutico, 1966 , vol. 105, p. 223,224 Full Text Show Details

Further information

FRENCH; TRUELOVE

Journal of pharmaceutical sciences, 1965 , vol. 54, p. 306 - 308 Title/Abstract Full Text Show Details

Further information

Smith et al.

Analytical Chemistry, 1963 , vol. 35, p. 58,60 Full Text Show Details

Further information

SINSHEIMER; SMITH

Journal of pharmaceutical sciences, 1963 , vol. 52, p. 1080 - 1085 Title/Abstract Full Text Show Details

Further information

Thies; Oezbilici

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1962 , vol. 295, p. 715,717 Full Text Show Details

Further information

Vidic; Schuette

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1962 , vol. 295, p. 342,358 Full Text Show Details

Optical Rotatory Power (2)

Type (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

[alpha]

22.2 deg

589 nm

[alpha]

38.4 deg

589 nm

Temperature (Optical Rotatory Power)

Reference G.D.Searle and Co.; Patent: GB831933 , 1960 ; Chem.Abstr., 1961 , vol. 55, # 2697b Full Text Show Details

18 °C

Chem.FabrikRavensberg GmbH, Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Reference

NMR

Spassov; Stefanovsky; Kurtev; Fodor

Chemische Berichte, 1972 , vol. 105, # 8 p. 2467 - 2475 Title/Abstract Full Text View citing articles Show Details

IR Spectroscopy (3) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Bands

neat (no solvent)

1135 - 702 cm**(-1)

Yordanova; Dantchev; Shvedov; Karanov

Archiv der Pharmazie, 1990 , vol. 323, # 1 p. 41 - 42 Title/Abstract Full Text View citing articles Show Details

Bands

neat (no solvent)

3363 - 1068 cm**(-1)

Marciniec

Pharmazie, 1985 , vol. 40, # 1 p. 30 - 33 Title/Abstract Full Text View citing articles Show Details

Reference

Hayden et al.

Journal - Association of Official Analytical Chemists, 1966 , vol. 49, p. 1109,1119 Full Text Show Details

Brannon; Hayden

Journal - Association of Official Analytical Chemists, 1964 , vol. 47, p. 918,962 Full Text Show Details

Mass Spectrometry (5) Description (Mass Spectrometry)

Comment (Mass Spectrometry)

Reference

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

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

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

Coutts,R.T. et al.

Biomedical Mass Spectrometry, 1975 , vol. 2, p. 137 - 141 Full Text View citing articles Show Details

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

Absorption Maxima (UV/VIS)

Reference

Absorption maxima

252 nm

Marciniec

Pharmazie, 1985 , vol. 40, # 1 p. 30 - 33 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (9) 1 of 9

Comment (Pharmacological Data)

Bioactivities present

Reference

Jilek,J.O. et al.

Collection of Czechoslovak Chemical Communications, 1971 , vol. 36, p. 2226 - 2247 Full Text View citing articles Show Details

Maurich; Rubessa

Bollettino Chimico Farmaceutico, 1973 , vol. 112, # 7 p. 465 - 471 Title/Abstract Full Text View citing articles Show Details

Cooper; Irving

Patent: US4255439 A1, 1981 ; Title/Abstract Full Text Show Details

Reisch; Alfes; Kommert; Jantos; Moellmann; Clasing

Die Pharmazie, 1970 , vol. 25, # 5 p. 331 - 334 Title/Abstract Full Text View citing articles Show Details

Pharmaquest Ltd.

Patent: US6217904 B1, 2001 ; Title/Abstract Full Text Show Details

Keown; Wendy J.; Ford; Betty J.; Stoddard; Sandra L.

Patent: US5543405 A1, 1996 ; Title/Abstract Full Text Show Details

Interneuron Pharmaceuticals, Inc.

Patent: US5096712 A1, 1992 ; Title/Abstract Full Text Show Details

Battey, Alyce S.; Battey, Jacob

Patent: US2002/22057 A1, 2002 ; Title/Abstract Full Text Show Details

Finke, Paul E.; Mills, Sander G.; Plummer, Christopher W.; Shah, Shrenik K.; Truong, Quang T.

Patent: US2003/114495 A1, 2003 ; Title/Abstract Full Text Show Details

Coutts,R.T. et al.

Biomedical Mass Spectrometry, 1975 , vol. 2, p. 137 - 141 Full Text View citing articles Show Details

GIANNINI; FEDI

Il Farmaco; edizione scientifica, 1965 , vol. 20, p. 176 - 193 Title/Abstract Full Text View citing articles Show Details

Klosa,J.

Journal fuer Praktische Chemie (Leipzig), 1963 , vol. 21, p. 12 - 17 Full Text View citing articles Show Details

SINSHEIMER; SMITH

Journal of pharmaceutical sciences, 1963 , vol. 52, p. 1080 - 1085 Title/Abstract Full Text Show Details

Beckett; Salami

The Journal of pharmacy and pharmacology, 1972 , vol. 24, # 11 p. 900 - 902 Title/Abstract Full Text View citing articles Show Details

The Research Foundation of the City University of New York; New York University

Patent: US7112319 B2, 2006 ; Title/Abstract Full Text Show Details

Gruenenthal GmbH

Patent: US2007/65365 A1, 2007 ; Title/Abstract Full Text Show Details

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

C.H. Boehringer Sohn Patent: US2835669 , 1953 ;

Full Text Show Details

HENGEN; SIEMER; DOPPSTADT

Arzneimittel-Forschung, 1958 , vol. 8, # 7 p. 421 - 423 Title/Abstract Full Text View citing articles Show Details

Searle and Co.

Patent: US2832777 , 1956 ; Full Text Show Details

2 of 9

3 of 9

Comment (Pharmacological Data)

Bioactivities present

Reference

Kolb; Patt

Arzneimittel-Forschung, 1965 , vol. 15, # 8 p. 924 - 927 Title/Abstract Full Text View citing articles Show Details

Reisch; Alfes; Moellmann

Die Pharmazie, 1968 , vol. 23, # 5 p. 245 - 246 Title/Abstract Full Text View citing articles Show Details

Palitzsch et al.

Pharmazie, 1968 , vol. 23, p. 246,248 Full Text Show Details

Hayden et al.

Journal - Association of Official Analytical Chemists, 1966 , vol. 49, p. 1109,1119 Full Text Show Details

Kuhnert-Brandstaetter et al.

Pharmaceutica Acta Helvetiae, 1975 , vol. 50, p. 360,364 Full Text Show Details

Sciortino

Bollettino Chimico Farmaceutico, 1966 , vol. 105, p. 223,224 Full Text Show Details

Smith et al.

Analytical Chemistry, 1963 , vol. 35, p. 58,60 Full Text Show Details

Egyesult Gyogyszer es Tapszergyar

Patent: HU149550 , 1960 ; Chem.Abstr., 1963 , vol. 58, # 4582d Full Text Show Details

Thies; Oezbilici

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1962 , vol. 295, p. 715,717 Full Text Show Details

Searle

Patent: US3074941 , 1961 ; Chem.Abstr., 1963 , vol. 59, # 10069c Full Text Show Details

Brannon; Hayden

Journal - Association of Official Analytical Chemists, 1964 , vol. 47, p. 918,962 Full Text Show Details

Kuhnert-Brandstaetter et al.

Scientia Pharmaceutica, 1964 , vol. 32, p. 308,310,320 Full Text Show Details

Vidic; Schuette

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1962 , vol. 295, p. 342,358 Full Text Show Details

FRENCH; TRUELOVE

Journal of pharmaceutical sciences, 1965 , vol. 54, p. 306 - 308 Title/Abstract Full Text Show Details

G.D.Searle and Co.; Patent: GB831933 , 1960 ; Chem.Abstr., 1961 , vol. 55, # 2697b Full Text Show Details Chem.FabrikRavensberg GmbH, Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details Chem,Fabrik Ravensberg GmbH, Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details Spassov; Stefanovsky; Kurtev; Fodor Chemische Berichte, 1972 , vol. 105, # 8 p. 2467 - 2475 Title/Abstract Full Text View citing articles Show Details

Portoghese

Journal of Medicinal Chemistry, 1967 , vol. 10, p. 1057 Full Text View citing articles Show Details

Shozokitagawa

Patent: JP623579 , 1962 ; Chem.Abstr., 1963 , vol. 58, # 9092h Full Text Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Danchev; Stoeva-Tordanova

Farmatsiya (Sofia, Bulgaria), 1972 , vol. 22, # 2 p. 1,3 Chem.Abstr., 1972 , vol. 77, # 101491f Full Text Show Details

Halmekoski; Lukkari

Suomen Kemistilehti B, 1964 , vol. 37, p. 183 Full Text Show Details

Ravensberg GmbH

Patent: GB816576 , 1955 ; Chem.Abstr., 1960 , # 1564 Full Text Show Details

Yordanova; Dantchev; Shvedov; Karanov

Archiv der Pharmazie, 1990 , vol. 323, # 1 p. 41 - 42 Title/Abstract Full Text View citing articles Show Details

Marciniec

Pharmazie, 1985 , vol. 40, # 3 p. 180 - 182 Title/Abstract Full Text View citing articles Show Details

Marciniec

Pharmazie, 1985 , vol. 40, # 1 p. 30 - 33 Title/Abstract Full Text View citing articles Show Details

Rucker; Mrongovius; Neugebauer

Archiv der Pharmazie, 1982 , vol. 315, # 10 p. 839 - 846 Title/Abstract Full Text View citing articles Show Details

Comai; Sullivan

Journal of Pharmaceutical Sciences, 1982 , vol. 71, # 4 p. 418 - 421 Title/Abstract Full Text View citing articles Show Details

The Procter and Gamble Company

Patent: US4557934 A1, 1985 ; Title/Abstract Full Text Show Details

Interneuron Pharmaceuticals, Inc.

Patent: US5019594 A1, 1991 ; Title/Abstract Full Text Show Details

Waleh, Nahid S.; Kilduff, Thomas S.

Patent: US2002/166135 A1, 2002 ; Title/Abstract Full Text Show Details

NEUROGESX, INC.

Patent: WO2008/70149 A2, 2008 ; Title/Abstract Full Text Show Details

CASE WESTERN RESERVE UNIVERSITY

Patent: WO2008/70264 A2, 2008 ; Title/Abstract Full Text Show Details

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

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

RESEARCH TRIANGLE INSTITUTE; UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES, C/O NATIONAL INSTITUTES OF HEALTH, OFFICE OF TECHNOLOGY TRANSFER; BLOUGH, Bruce E.; ROTHMAN, Richard; LANDAVAZO, Antonio; PAGE, Kevin M.; DECKER, Ann Marie

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Banks, Matthew L.; Blough, Bruce E.; Negus, S. Stevens

Behavioural Pharmacology, 2011 , vol. 22, # 8 p. 824 - 836 Title/Abstract Full Text View citing articles Show Details

Rothman, Richard B.; Baumann, Michael H.

Current Topics in Medicinal Chemistry, 2006 , vol. 6, # 17 p. 1845 - 1859 Title/Abstract Full Text View citing articles Show Details

Albert, Jeffrey S.; Blomberg, Niklas; Breeze, Alexander L.; Brown, Alastair J.H.; Burrows, Jeremy N.; Edwards, Philip D.; Folmer, Rutgers H.A.; Geschwindner, Stefan; Griffen, Ed J.; Kenny, Peter W.; Nowak, Thorsten; Olsson, Lise-Lotte; Sanganee, Hitesh; Shapiro, Adam B.

Current Topics in Medicinal Chemistry, 2007 , vol. 7, # 16 p. 1600 - 1629 Title/Abstract Full Text View citing articles Show Details

Esteki, Mahnaz; Khayamian, Taghi

Chemical Biology and Drug Design, 2008 , vol. 72, # 5 p. 409 - 435 Title/Abstract Full Text View citing articles Show Details

4 of 9

Comment (Pharmacological Data)

Bioactivities present

Reference

Benet, Leslie Z.; Broccatelli, Fabio; Oprea, Tudor I.

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Aeberli; Eden; Gogerty; Houlihan; Penberthy

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Ross; Renyi

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Faraj; Israili; Kight; Smissman; Pazdernik

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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

Freter; Goetz; Oliver

Journal of medicinal chemistry, 1970 , vol. 13, # 6 p. 1228 - 1230 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

HOLLAND; BUCK; WEISSMAN

Journal of medicinal chemistry, 1963 , vol. 6, p. 519 - 524 Title/Abstract Full Text Show Details

KNAPP

Journal of medicinal chemistry, 1964 , vol. 7, p. 433 - 439 Title/Abstract Full Text View citing articles Show Details

Donald R.Gehlert; David J. Goldstein; Philip A. Hipskind

Annual reports in medicinal chemistry, 1996 , vol. 31, p. 201 - 210 Title/Abstract Full Text Show Details

Frank P. Palopoli

Annual reports in medicinal chemistry, 1969 , vol. 5, p. 40 - 48 Title/Abstract Full Text Show Details

Frank P. Palopoli

Annual reports in medicinal chemistry, 1967 , vol. 3, p. 47 - 52 Title/Abstract Full Text Show Details

JOHN KRAPCHO; JOHN P. HIGH

Journal of medicinal chemistry, 1967 , vol. 10, # 3 p. 495 - 497 Title/Abstract Full Text 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

Allain, Florence; Minogianis, Ellie-Anna; Roberts, David C.S.; Samaha, Anne-Noël

Neuroscience and Biobehavioral Reviews, 2015 , vol. 56, p. 166 - 179 Title/Abstract Full Text View citing articles Show Details

Fialová, Magdaléna; Dvořák, Přemysl; Dušek, Petr; Kovalská, Petra; Šonka, Karel

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Choi, Hyeyoung; Kim, Suncheun; Ahn, Suyoun; Chang, Hyejin; Lee, Sangki; Lee, Yongmoon

Forensic Science International, 2016 , vol. 259, p. 69 - 76 Title/Abstract Full Text View citing articles Show Details

Ressler, Charles; Schneider, Stanley H.

Clinical Pharmacology and Therapeutics, 1961 , vol. 2, # 6 p. 727 - 732 Title/Abstract Full Text Show Details

Patel, Natoo; Mock, David C.; Hagans, James A.

Clinical Pharmacology and Therapeutics, 1963 , vol. 4, # 3 p. 330 - 333 Title/Abstract Full Text Show Details

5 of 9

Comment (Pharmacological Data)

Bioactivities present

Reference

Lemasson, Elise; Bertin, Sophie; West, Caroline

Journal of Separation Science, 2016 , vol. 39, # 1 p. 212 - 233 Title/Abstract Full Text View citing articles Show Details

McKay, Mary Pat; Groff, Loren

Accident Analysis and Prevention, 2016 , vol. 90, p. 108 - 117 Title/Abstract Full Text View citing articles Show Details

Gjerde, Hallvard; Nordfjærn, Trond; Bretteville-Jensen, Anne Line; Edland-Gryt, Marit; Furuhaugen, Håvard; Karinen, Ritva; Øiestad, Elisabeth L.

Forensic Science International, 2016 , vol. 265, p. 1 - 5 Title/Abstract Full Text View citing articles Show Details

Bauer, Clayton T.; Negus, S. Stevens; Blough, Bruce E.; Banks, Matthew L.

Behavioural Pharmacology, 2016 , vol. 27, # 2-3 p. 192 - 195 Title/Abstract Full Text View citing articles Show Details

Kim, Eunmi; Choe, Sanggil; Lee, Juseon; Jang, Moonhee; Choi, Hyeyoung; Chung, Heesun

Forensic Science International, 2016 , vol. 265, p. 186 - 192 Title/Abstract Full Text View citing articles Show Details

Czoty; Blough; Fennell; Snyder; Nader

Neuroscience, 2016 , vol. 324, p. 367 - 376 Title/Abstract Full Text View citing articles Show Details

Ponra, Sudipta; Majumdar

RSC Advances, 2016 , vol. 6, # 44 p. 37784 - 37922 Title/Abstract Full Text View citing articles Show Details

Stoops, William W.; Strickland, Justin C.; Hays, Lon R.; Rayapati, Abner O.; Lile, Joshua A.; Rush, Craig R.

Psychopharmacology, 2016 , vol. 233, # 11 p. 2055 - 2063 Title/Abstract Full Text View citing articles Show Details

Bolin, B. Levi; Stoops, William W.; Sites, Jeremy P.; Rush, Craig R.

Journal of Addiction Medicine, 2016 , vol. 10, # 3 p. 156 - 165 Title/Abstract Full Text View citing articles Show Details

Shekari, Ahmad; Akhgari, Maryam; Jokar, Farzaneh; Mousavi, Zahra

Journal of Substance Use, 2016 , vol. 21, # 5 p. 501 - 505 Title/Abstract Full Text View citing articles Show Details

Mardal, Marie; Miserez, Bram; Bade, Richard; Portolés, Tania; Bischoff, Markus; Hernández, Félix; Meyer, Markus R.

Journal of Pharmaceutical and Biomedical Analysis, 2016 , vol. 128, p. 485 - 495 Title/Abstract Full Text View citing articles Show Details

Olesen, Sanne H.; Zhu, Jin-Yi; Martin, Mathew P.; Schönbrunn, Ernst

ChemMedChem, 2016 , p. 1137 - 1144 Title/Abstract Full Text View citing articles Show Details

Solis, Ernesto; Suyama, Julie A.; Lazenka, Matthew F.; Defelice, Louis J.; Negus, S. Stevens; Blough, Bruce E.; Banks, Matthew L.

Scientific Reports, 2016 , vol. 6, art. no. 31385 Title/Abstract Full Text View citing articles Show Details

Beharry, Shruti; Gibbons, Simon

Forensic Science International, 2016 , vol. 267, p. 25 - 34 Title/Abstract Full Text View citing articles Show Details

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

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

Karkhanis, Anushree N.; Beveridge, Thomas J.R.; Blough, Bruce E.; Jones, Sara R.; Ferris, Mark J.

Drug and Alcohol Dependence, 2016 , vol. 166, p. 51 - 60 Title/Abstract Full Text View citing articles Show Details

Bäckberg, Matilda; Westerbergh, Jenny; Beck, Olof; Helander, Anders

Clinical Toxicology, 2016 , vol. 54, # 9 p. 819 - 825 Title/Abstract Full Text View citing articles Show Details

Onakpoya, Igho J.; Heneghan, Carl J.; Aronson, Jeffrey K.

BMC Medicine, 2016 , vol. 14, # 1 art. no. 191 Title/Abstract Full Text View citing articles Show Details

Schänzer, Wilhelm; Thevis, Mario

Mass Spectrometry Reviews, 2017 , vol. 36, # 1 p. 16 - 46 Title/Abstract Full Text View citing articles Show Details

6 of 9

7 of 9

8 of 9

Comment (Pharmacological Data)

Bioactivities present

Reference

Thiagarajan, Dheivya; Mehta, Dinesh P.

Journal of Chemical Information and Modeling, 2016 , vol. 56, # 12 p. 2310 - 2319 Title/Abstract Full Text View citing articles Show Details

Garvey, W. Timothy; Mechanick, Jeffrey I.; Brett, Elise M.; Garber, Alan J.; Hurley, Daniel L.; Jastreboff, Ania M.; Nadolsky, Karl; Pessah-Pollack, Rachel; Plodkowski, Raymond

Endocrine Practice, 2016 , vol. 22, p. 1 - 203 Title/Abstract Full Text View citing articles Show Details

Akhgari, Maryam; Mobaraki, Homeira; Etemadi-Aleagha, Afshar

DARU, Journal of Pharmaceutical Sciences, 2017 , vol. 25, # 1 art. no. 5 Title/Abstract Full Text View citing articles Show Details

Kong, Tae Yeon; Kim, Ju Hyun; Kim, Jin Young; In, Moon Kyo; Choi, Kyung Ho; Kim, Hee Seung; Lee, Hye Suk

Archives of Pharmacal Research, 2017 , vol. 40, # 2 p. 180 - 196 Title/Abstract Full Text View citing articles Show Details

McLaughlin, Gavin; Morris, Noreen; Kavanagh, Pierce V.; Dowling, Geraldine; Power, John D.; Twamley, Brendan; O'Brien, John; Talbot, Brian; Sitte, Harald H.; Brandt, Simon D.

Drug Testing and Analysis, 2017 , vol. 9, # 3 p. 369 - 377 Title/Abstract Full Text Show Details

Brandt, Simon D.; Kavanagh, Pierce V.

Drug Testing and Analysis, 2017 , vol. 9, # 3 p. 342 - 346 Title/Abstract Full Text Show Details

Odoardi, Sara; Valentini, Valeria; De Giovanni, Nadia; Pascali, Vincenzo Lorenzo; Strano-Rossi, Sabina

Microchemical Journal, 2017 , vol. 133, p. 302 - 310 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Olesen, Sanne H.; Zhu, Jin-Yi; Martin, Mathew P.; Schönbrunn, Ernst

ChemMedChem, 2016 , p. 1137 - 1144 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cocaine self-administration; increase of

Species or TestSystem (Pharmacological Data)

rhesus monkey of Macaca mulatta; pre-existing medical conditions: cocaine addiction

Sex

male

Route of Application

intravenous

Kind of Dosing (Pharmacological Data)

title comp. administered as fumarate using syringe pump at dose 0.032 - 0.32 mg/kg/h; title comp. dissolved in sterile water

9 of 9

Further Details (Pharmacological Data)

cocaine versus food choice determined; cocaine choice ED50 in control (baseline): 0.017 mg/kg/injection; cocaine choice ED50: dose of cocaine that produced 50percent cocaine choice

Type (Pharmacological Data)

cocaine choice ED50

Value of Type (Pharmacological Data)

0.024 - 0.055 mg/kg/injection

Reference

Banks, Matthew L.; Blough, Bruce E.; Negus, S. Stevens

Behavioural Pharmacology, 2011 , vol. 22, # 8 p. 824 - 836 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

inhibition of rat pancreatic lipase

Reference

Comai; Sullivan

Journal of Pharmaceutical Sciences, 1982 , vol. 71, # 4 p. 418 - 421 Title/Abstract Full Text View citing articles Show Details

Other Data Use (17) Use Pattern

Reference

anorexiant

NEUROGESX, INC.

Patent: WO2008/70149 A2, 2008 ; Title/Abstract Full Text Show Details

Decongestant

CASE WESTERN RESERVE UNIVERSITY

Patent: WO2008/70264 A2, 2008 ; Title/Abstract Full Text Show Details

epilepsy

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

diabetes

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

hypertension

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

pulmonary hypertension

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

migraine

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

sleep apnea

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

depression

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

impulse control disorders

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ;

alcohol addiction

Title/Abstract Full Text Show Details

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ;

sympathomimetic agent

Title/Abstract Full Text Show Details

second agent of the composition with antiepileptic agent

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

second agent of the composition with anticonvulsant sulfamate or sulfonylurea compound

Tam, Peter Y.; Wilson, Leland F.

Patent: US2008/103179 A1, 2008 ; Title/Abstract Full Text Show Details

gel-forming agent for an abuse-resistant transdermal system

Gruenenthal GmbH

Patent: US2007/65365 A1, 2007 ; Title/Abstract Full Text Show Details

The Research Foundation of the City University of New York; New York University

Patent: US7112319 B2, 2006 ;

stimulant effect on the central nervous system

Title/Abstract Full Text Show Details

The Research Foundation of the City University of New York; New York University

Patent: US7112319 B2, 2006 ;

Stimulant

Title/Abstract Full Text Show Details

Chemical Name: 3-methyl-2-phenyl-morpholine Reaxys Registry Number: 1211811

CAS Registry Number: 134-49-6, 1618-50-4, 13580-23-9, 57919-127, 63971-50-6, 84025-82-1 Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-BFHBGLAWSA-N

1 prep out of 1 reactions.

Identification Bioactivity (5)

Synthesize | Hide Details Find similar Chemical Names and Synonyms 3-methyl-2-phenyl-morpholine, PAL55 Identification Patent-Specific Data (1) Related Markush Structure (RN) 22041163; 22041164

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Derivative (1)

Comment (Derivative)

Reference

HCl:F:176-178.6grad

Geigy Chem.

Patent: US3282936 , 1966 ; Chem.Abstr., vol. 66, # 65485 Full Text Show Details

Bioactivity Pharmacological Data (5) 1 of 5

Comment (Pharmacological Data)

Bioactivities present

Reference

Geigy Chem.

Patent: US3282936 , 1966 ; Chem.Abstr., vol. 66, # 65485 Full Text Show Details

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

2 of 5

Effect (Pharmacological Data)

dopamine (DA); release of

Species or TestSystem (Pharmacological Data)

caudate of rat

Method (Pharmacological Data)

Example 4 - DA, NE, 5-HT Release AssaysA series of compounds were assayed for release of dopamine, serotonin, and norepinephrine as well as for activity at the 5-HT2B receptor. This data is shown below in Table 3.DA, NE and 5-HT Release Assays[3H]MPP+ was used as the

radioligand for both the DA and NE release assays, because this method led to an improved signal-to-noise ratio. Rat caudate (for DA release) or whole brain minus cerebellum and caudate (for NE and 5-HT release), was homogenized in ice-cold 10percent sucrose containing 1 μΜ reserpine. Nomifensine (100 nM) and GBR12935 (100 nM) were added to the sucrose solution for [3H]5-HT release experiments to block any potential [3H]5-HT reuptake into NE and DA nerve terminals. For the DA release assay, 100 nM desipramine and 100 nM citalopram were added to block [3H]MPP+ uptake into NE and 5-HT nerves. For the NE release assay, 50 nMGBR12935 and 100 nM citalopram were added to block [3H]MPP+ uptake into DA and 5-HT nerves. After 12 strokes with a Potter-Elvehjem homogenizer, homogenates were centrifuged at 1000 x g for 10 min at 0^1 °C and the supernatants were retained on ice (synaptosomal preparation).Synaptosomal preparations were incubated to steady state with 5 nM [3H]MPP+ (60 min) or 5 nM [3H]5-HT (60 min) in Krebsphosphate buffer (without BSA) (pH 7.4), which contained 154.4 mM aCl, 2.9 mM KC1, 1.1 mM CaCl2, 0.83 mM MgCl2, 5 mM glucose, 1 mg/mL ascorbic acid, 50 μΜ pargyline plus 1 μΜ reserpine in a polypropylene beaker with stirring at 25 °C with the appropriate blockers. After incubation to steady state, 850 μ of synaptosomes preloaded with [3H]ligand were added to 12 x 75 mm polystyrene test tubes that contained 150 μ test drug in uptake buffer plus 1 mg/ml BSA. After 5 min (3H]5-HT) or 30 min (NE and DA assays) the release reaction was terminated by dilution with 4 ml wash buffer (10 mM Tris-HCl pH 7.4 containing 0.9percent NaCl at 25 °C) followed by rapid vacuum filtration over Whatman GF/B filters using a Brandel Harvester. The filters were rinsed twice with 4 ml wash buffer using the Brandel Harvester, and the retained tritium was counted by a Taurus liquid scintillation counter at 40percent efficiency after an overnight extraction in 3 ml Cytoscint (ICN).Substrate Reversal ExperimentsFor substrate reversal experiments, test drugs were tested at approximately EDgo doses in the absence and presence of blockers (250 nM GBR1209 for DAT, 166 nM desipramine for NET, 100 nM fluoxetine for SERT). Substrate activity was detected by a significant reversal of the releasing effect of the test drug.Data analysis and statisticsAs previously described (Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI and Partilla JS Synapse 39: 32-41 (2001), incorporated herein by reference), EC50 values were determined using the nonlinear least squares curve fitting program MLAB-PC (Civilized Software, Bethesda, MD). In substrate reversal experiments, statistical significance was determined using the Student's t-test.

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

131 nmol/l

Location

Page/Page column 81-82

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

3 of 5

Effect (Pharmacological Data)

serotonin (5-HT); release of

Species or TestSystem (Pharmacological

whole brain minus cerebellum and caudate of rat

Data) Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

7765 nmol/l

Location

Page/Page column 81-82

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

4 of 5

Effect (Pharmacological Data)

norepinephrine (NE); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

50 nmol/l

Location

Page/Page column 81-82

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

5 of 5

Effect (Pharmacological Data)

serotonin (5-HT2B) receptor; agonist

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Location

Page/Page column 81-82

Comment (Pharmacological Data)

No effect

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Chemical Name: (+)-phenmetrazine Reaxys Registry Number: 4134180

CAS Registry Number: 57919-12-7 Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-GXSJLCMTSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-phenmetrazine, (2S)-trans-3-methyl-2-phenyl-morpholine, D-3-Methyl-2-phenyl-morpholin, PAL57 Identification Substance Label (3)

1 prep out of 3 reactions.

Identification Physical Data (3) Bioactivity (16)

Label

Reference

(+)-2

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

2S,3S-(+)-23

Perrone; Bettoni; Tortorella

Archiv der Pharmazie, 1983 , vol. 316, # 7 p. 617 - 624 Title/Abstract Full Text View citing articles Show Details

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (1) Related Markush Structure (RN) 22041163; 22041164

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Physical Data Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

80 °C

0.4 Torr

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Circular Dichroism (1) Solvent (Circular Dichroism)

Comment (Circular Dichroism)

Reference

methanol

249 - 265 nm

Perrone; Bettoni; Tortorella

Archiv der Pharmazie, 1983 , vol. 316, # 7 p. 617 - 624 Title/Abstract Full Text View citing articles Show Details

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

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

22.8 deg

589 nm

26 °C

Reference KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (16) 1 of 16

Comment (Pharmacological Data)

Bioactivities present

Reference

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Perrone; Bettoni; Tortorella

Archiv der Pharmazie, 1983 , vol. 316, # 7 p. 617 - 624 Title/Abstract Full Text View citing articles Show Details

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

2 of 16

Effect (Pharmacological Data)

dopamine (DA); release of

Species or TestSystem (Pharmacological Data)

caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

415 nmol/l

Location

Page/Page column 81-82

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

3 of 16

Effect (Pharmacological Data)

serotonin (5-HT); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

in 3 ml Cytoscint (ICN).Substrate Reversal ExperimentsFor substrate reversal experiments, test drugs were tested at approximately EDgo doses in the absence and presence of blockers (250 nM GBR1209 for DAT, 166 nM desipramine for NET, 100 nM fluoxetine for SERT). Substrate activity was detected by a significant reversal of the releasing effect of the test drug.Data analysis and statisticsAs previously described (Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI and Partilla JS Synapse 39: 32-41 (2001), incorporated herein by reference), EC50 values were determined using the nonlinear least squares curve fitting program MLAB-PC (Civilized Software, Bethesda, MD). In substrate reversal experiments, statistical significance was determined using the Student's t-test. Location

Page/Page column 81-82

Comment (Pharmacological Data)

No effect

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

4 of 16

Effect (Pharmacological Data)

norepinephrine (NE); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

63 nmol/l

Location

Page/Page column 81-82

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

5 of 16

Effect (Pharmacological Data)

serotonin (5-HT2B) receptor; agonist

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

citalopram were added to block [3H]MPP+ uptake into NE and 5-HT nerves. For the NE release assay, 50 nMGBR12935 and 100 nM citalopram were added to block [3H]MPP+ uptake into DA and 5-HT nerves. After 12 strokes with a Potter-Elvehjem homogenizer, homogenates were centrifuged at 1000 x g for 10 min at 0^1 °C and the supernatants were retained on ice (synaptosomal preparation).Synaptosomal preparations were incubated to steady state with 5 nM [3H]MPP+ (60 min) or 5 nM [3H]5-HT (60 min) in Krebsphosphate buffer (without BSA) (pH 7.4), which contained 154.4 mM aCl, 2.9 mM KC1, 1.1 mM CaCl2, 0.83 mM MgCl2, 5 mM glucose, 1 mg/mL ascorbic acid, 50 μΜ pargyline plus 1 μΜ reserpine in a polypropylene beaker with stirring at 25 °C with the appropriate blockers. After incubation to steady state, 850 μ of synaptosomes preloaded with [3H]ligand were added to 12 x 75 mm polystyrene test tubes that contained 150 μ test drug in uptake buffer plus 1 mg/ml BSA. After 5 min (3H]5-HT) or 30 min (NE and DA assays) the release reaction was terminated by dilution with 4 ml wash buffer (10 mM Tris-HCl pH 7.4 containing 0.9percent NaCl at 25 °C) followed by rapid vacuum filtration over Whatman GF/B filters using a Brandel Harvester. The filters were rinsed twice with 4 ml wash buffer using the Brandel Harvester, and the retained tritium was counted by a Taurus liquid scintillation counter at 40percent efficiency after an overnight extraction in 3 ml Cytoscint (ICN).Substrate Reversal ExperimentsFor substrate reversal experiments, test drugs were tested at approximately EDgo doses in the absence and presence of blockers (250 nM GBR1209 for DAT, 166 nM desipramine for NET, 100 nM fluoxetine for SERT). Substrate activity was detected by a significant reversal of the releasing effect of the test drug.Data analysis and statisticsAs previously described (Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI and Partilla JS Synapse 39: 32-41 (2001), incorporated herein by reference), EC50 values were determined using the nonlinear least squares curve fitting program MLAB-PC (Civilized Software, Bethesda, MD). In substrate reversal experiments, statistical significance was determined using the Student's t-test. Location

Page/Page column 81-82

Comment (Pharmacological Data)

No effect

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

6 of 16

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 2 nmol/l <3H>DHTBZ for 4 h at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>DHTBZ binding

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

7 of 16

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 60 nmol/l <3H>dopamine for 5 min at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>dopamine uptake

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data) Reference

> 100 μmol/l

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246

Title/Abstract Full Text View citing articles Show Details

8 of 16

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction preloaded with 60 nmol/l <3H>tyramine for 20 min at 25 deg C, incubated with title comp. for 2 min at 25 deg C; rapid filtration; liquid scintillation counting; <3H>tyramine release evaluated

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>tyramine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

9 of 16

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction preloaded with 60 nmol/l <3H>dopamine for 20 min at 25 deg C, incubated with title comp. for 10 min at 25 deg C; rapid filtration; liquid scintillation counting; <3H>dopamine release evaluated

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>dopamine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

10 of 16

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intravenous

Method (Pharmacological Data)

rats administered with title comp.; extention tubes connected to catheters, microdialysis probes into nucleus accumbens; perfused with artificial cerebrospinal fluid; dialysate collected at 20 min interval; assayed for endogenous dopamine, 5-HT by HPLC

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. increased extracellular dopamine, and extracellular 5-HT to lesser extent in dose-dependent manner; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57

Title/Abstract Full Text View citing articles Show Details

11 of 16

12 of 16

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incubated to steady state with <3H>5-HT for 30 min; title comp. added, incubated with <3H>5-HT for 60 min; 5-HT (serotonin) release (non-displaceable tritium) determined with tyramine (10 μmol/l) by microplate and scintillation counter

Further Details (Pharmacological Data)

<3H>5-HT release performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

3246 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incubated to steady state with <3H>5-HT for 30 min; title comp. added, incubated with <3H>5-HT for 5 min; 5-HT (serotonin) re-uptake (non-displaceable tritium) determined with tyramine (10 μmol/l) by microplate and scintillation counter

Further Details (Pharmacological Data)

<3H>5-HT re-uptake performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

13 of 16

> 100000 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incub. to steady state with <3H>norepinephrine for 60 min; added to title comp., incub. with <3H>norepinephrine for 30 min; norepinephrine release (non-displaceable tritium) detd. with tyramine by microplate, scintillation counter

Further Details (Pharmacological Data)

<3H>norepinephrine release performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological

EC50

Data)

14 of 16

15 of 16

16 of 16

Value of Type (Pharmacological Data)

37.5 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incub. to steady state with <3H>norepinephrine for 10 min; added to title comp., incub. with <3H>norepinephrine for 30 min; norepinephrine re-uptake (non-displaceable tritium) detd. with tyramine using microplate, scintillation counter

Further Details (Pharmacological Data)

<3H>norepinephrine re-uptake performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

240 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incubated to steady state with <3H>dopamine for 15 min; title comp. added, incubated with <3H>dopamine for 5 min; dopamine re-uptake (non-displaceable tritium) determined with tyramine (10 μmol/l) by microplate and scintillation counter

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

359 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incub. to steady state with <3H>dopamine for 30 min; added to title comp., incub. with <3H>dopamine for 5 min; dopamine release (non-displaceable tritium) detd. by incubating with tyramine using microplate, scintillation counter

Further Details

references: (+)-methamphetamine, indatraline; further study with indatraline

(Pharmacological Data) Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

87.4 nmol/l

Results

indatraline reversed the releasing effect of title comp.; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Chemical Name: trans-Phenmetrazine Reaxys Registry Number: 4134181

InChI Key: OOBHFESNSZDWIU-GXSJLCMTSA-N

5 prep out of 45 reactions.

Identification Physical Data (2) Spectra (6) Bioactivity (7)

Synthesize | Hide Details Find similar Chemical Names and Synonyms trans-Phenmetrazine, phenmetrazine, 3-methyl-2-phenyl-morpholine, (+-)-trans-3-Methyl-2-phenyl-morpholin, DL-3-Methyl-2-phenyl-morpholin Identification Substance Label (4) Label

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Perrone; Carbonara; Tortorella

Archiv der Pharmazie, 1984 , vol. 317, # 1 p. 21 - 27 Title/Abstract Full Text View citing articles Show Details

Perrone, Roberto; Berardi, Francesco; Tortorella, Vincenzo

Gazzetta Chimica Italiana, 1983 , vol. 113, # 7/8 p. 521 - 522 Title/Abstract Full Text Show Details

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Derivative (2) Comment (Derivative)

Reference

Hydrochlorid C11H15NO*HCl: F : 180 - 181grad<aus Ethanol + Diethylether>

Clarke

Journal of Organic Chemistry, 1962 , vol. 27, p. 3251 Full Text View citing articles Show Details

Pikrat C11H15NO*C6H3N3O7 : F: 200 - 202grad<aus Ethanol>

Clarke

Journal of Organic Chemistry, 1962 , vol. 27, p. 3251 Full Text View citing articles Show Details

Physical Data

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

87 - 88 °C

0.8 Torr

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Refractive Index (1) Refractive Index

Wavelength (Refractive Index)

Temperature (Refractive Index)

Reference

1.5376

589 nm

25 °C

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (3) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Temperature (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts Spectrum

chloroform-d1

26.84 °C

Chemical shifts

13C

chloroform-d1

27.04 °C

Chemical shifts

CDCl3

Location

Reference

500 MHz

supporting information

Zhou, Ling; Tan, Chong Kiat; Zhou, Jing; Yeung, Ying-Yeung

Journal of the American Chemical Society, 2010 , vol. 132, # 30 p. 10245 - 10247 Title/Abstract Full Text View citing articles Show Details

75 MHz

supporting information

Zhou, Ling; Tan, Chong Kiat; Zhou, Jing; Yeung, Ying-Yeung

Journal of the American Chemical Society, 2010 , vol. 132, # 30 p. 10245 - 10247 Title/Abstract Full Text View citing articles Show Details

Perrone; Carbonara; Tortorella

Archiv der Pharmazie, 1984 , vol. 317, # 1 p. 21 - 27 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (3) Description (Mass Spectrometry)

Location

Reference

ESI (Electrospray ionisation) Spectrum

supporting information

Zhou, Ling; Tan, Chong Kiat; Zhou, Jing; Yeung, Ying-Yeung

Journal of the American Chemical Society, 2010 , vol. 132, # 30 p. 10245 - 10247 Title/Abstract Full Text View citing articles Show Details

spectrum electron impact (EI)

Perrone; Carbonara; Tortorella

Archiv der Pharmazie, 1984 , vol. 317, # 1 p. 21 - 27 Title/Abstract Full Text View citing articles Show Details

spectrum

Perrone, Roberto; Berardi, Francesco; Tortorella, Vincenzo

Gazzetta Chimica Italiana, 1983 , vol. 113, # 7/8 p. 521 - 522 Title/Abstract Full Text Show Details

Bioactivity Pharmacological Data (7) 1 of 7

Comment (Pharmacological Data)

Bioactivities present

Reference

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Clarke

Journal of Organic Chemistry, 1962 , vol. 27, p. 3251 Full Text View citing articles Show Details

Perrone; Carbonara; Tortorella

Archiv der Pharmazie, 1984 , vol. 317, # 1 p. 21 - 27

Title/Abstract Full Text View citing articles Show Details

Perrone, Roberto; Berardi, Francesco; Tortorella, Vincenzo

Gazzetta Chimica Italiana, 1983 , vol. 113, # 7/8 p. 521 - 522 Title/Abstract Full Text Show Details

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Zhou, Ling; Tan, Chong Kiat; Zhou, Jing; Yeung, Ying-Yeung

Journal of the American Chemical Society, 2010 , vol. 132, # 30 p. 10245 - 10247 Title/Abstract Full Text View citing articles Show Details

2 of 7

3 of 7

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT release performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

7765 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT re-uptake performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

4 of 7

> 100000 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

5 of 7

6 of 7

7 of 7

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine release performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

50.4 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine re-uptake performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

153 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

607 nmol/l

Results

title comp. stereoselectively inhibited <3H>dopamine uptake; table

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

synaptosomes incub. to steady state with <3H>dopamine for 30 min; added to title comp., incub. with <3H>dopamine for 5 min; dopamine release (non-displaceable tritium) detd. by conducting incub. with tyramine using microplate, scintillation counter

Further Details (Pharmacological Data)

references: (+)-methamphetamine, indatraline; further study with indatraline

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

131 nmol/l

Results

indatraline reversed the releasing effect of title comp.; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Chemical Name: pseudophenmetrazine Reaxys Registry Number: 4134182

InChI Key: OOBHFESNSZDWIU-MWLCHTKSSA-N

1 prep out of 1 reactions.

Identification Bioactivity (7)

Synthesize | Hide Details Find similar Chemical Names and Synonyms pseudophenmetrazine, 3-methyl-2-phenyl-morpholine, (+-)-cis-3-Methyl-2-phenyl-morpholin Identification Substance Label (1) Label

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Derivative (2) Comment (Derivative)

Reference

Hydrochlorid C11H15NO*HCl: F : 152 - 154grad<aus Ethanol + Diethylether>

Clarke

Journal of Organic Chemistry, 1962 , vol. 27, p. 3251 Full Text View citing articles Show Details

Pikrat C11H15NO*C6H3N3O7 : F: 210 - 211grad<aus Ethanol>

Clarke

Journal of Organic Chemistry, 1962 , vol. 27, p. 3251 Full Text View citing articles Show Details

Bioactivity Pharmacological Data (7)

1 of 7

2 of 7

Comment (Pharmacological Data)

Bioactivities present

Reference

Clarke

Journal of Organic Chemistry, 1962 , vol. 27, p. 3251 Full Text View citing articles Show Details

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT release performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

3 of 7

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT re-uptake performed in presence of nomifensine (100 nmol/l) and GBR12935; IC50: inhibition of reuptake by title comp.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

4 of 7

> 100000 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

5 of 7

6 of 7

7 of 7

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine release performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

514 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine re-uptake performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

453 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

references: (+)-methamphetamine, indatraline; further study with indatraline

Results

title comp. showed weak <3H>dopamine release; table; indatraline reversed the releasing effect of title comp.; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2630 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (-)-phenmetrazine Reaxys Registry Number: 4795933

CAS Registry Number: 497180-74-2 Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-KOLCDFICSA-N

1 prep out of 3 reactions.

Identification Physical Data (2) Bioactivity (16)

Synthesize | Hide Details Find similar Chemical Names and Synonyms (-)-phenmetrazine, (2R)-trans-3-methyl-2-phenyl-morpholine, L-3-Methyl-2-phenyl-morpholin, PAL56 Identification Substance Label (2) Label

Reference

(-)-2

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (1) Related Markush Structure (RN) 22041163; 22041164

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Physical Data Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

90 - 93 °C

1.1 Torr

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

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

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

-21.9 deg

589 nm

26 °C

Reference KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (16) 1 of 16

Comment (Pharmacological Data)

Bioactivities present

Reference

KALM

Journal of medicinal chemistry, 1964 , vol. 7, p. 427 - 433 Title/Abstract Full Text View citing articles Show Details

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

2 of 16

Effect (Pharmacological Data)

dopamine (DA); release of

Species or TestSystem (Pharmacological Data)

caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

87 nmol/l

Location

Page/Page column 81-82; 85

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

3 of 16

Effect (Pharmacological Data)

serotonin (5-HT); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

3246 nmol/l

Location

Page/Page column 81-82; 85

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

4 of 16

Effect (Pharmacological Data)

norepinephrine (NE); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

described (Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI and Partilla JS Synapse 39: 32-41 (2001), incorporated herein by reference), EC50 values were determined using the nonlinear least squares curve fitting program MLAB-PC (Civilized Software, Bethesda, MD). In substrate reversal experiments, statistical significance was determined using the Student's t-test. Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

37 - 38 nmol/l

Location

Page/Page column 81-82; 85

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

5 of 16

Effect (Pharmacological Data)

serotonin (5-HT2B) receptor; agonist

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Location

Page/Page column 81-82

Comment (Pharmacological Data)

No effect

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

6 of 16

Effect (Pharmacological Data)

serotonin (5-HT2B) receptor; antagonist

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

homogenates were centrifuged at 1000 x g for 10 min at 0^1 °C and the supernatants were retained on ice (synaptosomal preparation).Synaptosomal preparations were incubated to steady state with 5 nM [3H]MPP+ (60 min) or 5 nM [3H]5-HT (60 min) in Krebsphosphate buffer (without BSA) (pH 7.4), which contained 154.4 mM aCl, 2.9 mM KC1, 1.1 mM CaCl2, 0.83 mM MgCl2, 5 mM glucose, 1 mg/mL ascorbic acid, 50 μΜ pargyline plus 1 μΜ reserpine in a polypropylene beaker with stirring at 25 °C with the appropriate blockers. After incubation to steady state, 850 μ of synaptosomes preloaded with [3H]ligand were added to 12 x 75 mm polystyrene test tubes that contained 150 μ test drug in uptake buffer plus 1 mg/ml BSA. After 5 min (3H]5-HT) or 30 min (NE and DA assays) the release reaction was terminated by dilution with 4 ml wash buffer (10 mM Tris-HCl pH 7.4 containing 0.9percent NaCl at 25 °C) followed by rapid vacuum filtration over Whatman GF/B filters using a Brandel Harvester. The filters were rinsed twice with 4 ml wash buffer using the Brandel Harvester, and the retained tritium was counted by a Taurus liquid scintillation counter at 40percent efficiency after an overnight extraction in 3 ml Cytoscint (ICN).Substrate Reversal ExperimentsFor substrate reversal experiments, test drugs were tested at approximately EDgo doses in the absence and presence of blockers (250 nM GBR1209 for DAT, 166 nM desipramine for NET, 100 nM fluoxetine for SERT). Substrate activity was detected by a significant reversal of the releasing effect of the test drug.Data analysis and statisticsAs previously described (Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI and Partilla JS Synapse 39: 32-41 (2001), incorporated herein by reference), EC50 values were determined using the nonlinear least squares curve fitting program MLAB-PC (Civilized Software, Bethesda, MD). In substrate reversal experiments, statistical significance was determined using the Student's t-test. Results

antagonist (percent) = 42 at 10 μmol/l

Location

Page/Page column 81-82

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

7 of 16

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 2 nmol/l <3H>DHTBZ for 4 h at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>DHTBZ binding

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

8 of 16

9 of 16

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 60 nmol/l <3H>dopamine for 5 min at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>dopamine uptake

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

90.0 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect

transmitter releasing

(Pharmacological Data) Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>tyramine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

10 of 16

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>dopamine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

11 of 16

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT release performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data) Reference

> 100000 nmol/l

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

12 of 16

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

14 of 16

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT re-uptake performed in presence of nomifensine (100 nmol/l) and GBR12935; IC50: inhibition of reuptake by title comp.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

13 of 16

transport; inhibition of

> 100000 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine release performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

62.9 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinerphrine re-uptake performed in presence of 3β-(4-Iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

IC50

15 of 16

16 of 16

Value of Type (Pharmacological Data)

388 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

references: (+)-methamphetamine, indatraline; further study with indatraline

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

415 nmol/l

Results

indatraline reversed the releasing effect of title comp.; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

1669 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (-)-(2R,3S)-3-Methyl-2-phenylmorpholin

Reaxys Registry Number: 6478372

CAS Registry Number: 84025-82-1 Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-ONGXEEELSA-N

2 prep out of 5 reactions.

Identification Physical Data (1) Bioactivity (7)

Synthesize | Hide Details Find similar Chemical Names and Synonyms (-)-(2R,3S)-3-Methyl-2-phenylmorpholin, (-)-pseudophenmetrazine Identification Substance Label (2) Label

Reference

Garnier, Jean Marc; Robin, Sylvie; Rousseau, Gerard

European Journal of Organic Chemistry, 2007 , # 20 p. 3281 - 3291 Title/Abstract Full Text View citing articles Show Details

(-)-3

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Physical Data Optical Rotatory Power (1) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

2 g/100ml

aq. HCl

-51.6 deg

589 nm

25 °C

Reference Blarer, Stefan J.; Schweizer, W. Bernd; Seebach, Dieter Helvetica Chimica Acta, 1982 , vol. 65, # 5 p. 1637 - 1654 Title/Abstract Full Text Show Details

Bioactivity Pharmacological Data (7) 1 of 7

2 of 7

Comment (Pharmacological Data)

Bioactivities present

Reference

Blarer, Stefan J.; Schweizer, W. Bernd; Seebach, Dieter

Helvetica Chimica Acta, 1982 , vol. 65, # 5 p. 1637 - 1654 Title/Abstract Full Text Show Details

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Garnier, Jean Marc; Robin, Sylvie; Rousseau, Gerard

European Journal of Organic Chemistry, 2007 , # 20 p. 3281 - 3291 Title/Abstract Full Text View citing articles Show Details

Rothman, Richard B.; Baumann, Michael H.

Current Topics in Medicinal Chemistry, 2006 , vol. 6, # 17 p. 1845 - 1859 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT release performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological

EC50

Data) Value of Type (Pharmacological Data)

3 of 7

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT re-uptake performed in presence of nomifensine (100 nmol/l) and GBR12935; IC50: inhibition of reuptake by title comp.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

4 of 7

5 of 7

> 100000 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine release performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2511 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method

synaptosomes incub. to steady state with <3H>norepinephrine for 10 min; added to title comp., incub. with <3H>norepinephrine for 30

6 of 7

7 of 7

(Pharmacological Data)

min; norepinephrine re-uptake (non-displaceable tritium) detd. with tyramine using microplate, scintillation counter

Further Details (Pharmacological Data)

<3H>norepinerphrine re-uptake performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2512 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

references: (+)-methamphetamine, indatraline; further study with indatraline

Results

title comp. showed weak <3H>dopamine release; table; indatraline reversed the releasing effect of title comp.; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2691 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (+)-pseudophenmetrazine Reaxys Registry Number: 10470152

Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N

no reactions.

Bioactivity (5)

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-pseudophenmetrazine Bioactivity Pharmacological Data (5) 1 of 5

2 of 5

Comment (Pharmacological Data)

Bioactivities present

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 2 nmol/l <3H>DHTBZ for 4 h at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>DHTBZ binding

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3 of 5

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 60 nmol/l <3H>dopamine for 5 min at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>dopamine uptake

Type (Pharmacological

IC50

Data)

4 of 5

Value of Type (Pharmacological Data)

92.0 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>tyramine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

5 of 5

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

Further Details (Pharmacological Data)

EC50 for title comp. inhibition of <3H>dopamine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data) Reference

> 100 μmol/l

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (-)-pseudophenmetrazine Reaxys Registry Number: 10473092

Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-UHFFFAOYSA-N

Synthesize | Hide Details

no reactions.

Bioactivity (5)

Find similar Chemical Names and Synonyms (-)-pseudophenmetrazine Bioactivity Pharmacological Data (5) 1 of 5

2 of 5

Comment (Pharmacological Data)

Bioactivities present

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 2 nmol/l <3H>DHTBZ for 4 h at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>DHTBZ binding

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3 of 5

4 of 5

> 100 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

monoamine transporter; interaction with

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

vesicular fraction incubated with title comp. and 60 nmol/l <3H>dopamine for 5 min at 25 deg C; rapid filtration; liquid scintillation counting

Further Details (Pharmacological Data)

DHTBZ: dihydrotetrabenazine; VMAT2: vesicular monoamine transporter type 2; IC50 for title comp. inhibition of <3H>dopamine uptake

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

22.7 μmol/l

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

5 of 5

Method (Pharmacological Data)

Further Details (Pharmacological Data)

EC50 and EMAX for title comp. inhibition of <3H>tyramine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

19.2 μmol/l

Results

EMAX = 105 percent

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat caudate putamen crude vesicular fraction

Method (Pharmacological Data)

Further Details (Pharmacological Data)

EC50 and EMAX for title comp. inhibition of <3H>dopamine release

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

12.1 μmol/l

Results

EMAX = 72.5 percent

Reference

Partilla, John S.; Dempsey, Allison G.; Nagpal, Ameet S.; Blough, Bruce E.; Baumann, Michael H.; Rothman, Richard B.

Journal of Pharmacology and Experimental Therapeutics, 2006 , vol. 319, # 1 p. 237 - 246 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (+)-pseudophenmetrazine

no reactions.

Reaxys Registry Number: 10657357

Type of Substance: heterocyclic Molecular Formula: C11H15NO Linear Structure Formula: C11H15NO Molecular Weight: 177.246

InChI Key: OOBHFESNSZDWIU-MWLCHTKSSA-N 10

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-pseudophenmetrazine, PAL60 Identification Substance Label (1) Label

Reference

(+)-3

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57

Identification Bioactivity (11)

Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (1) Related Markush Structure (RN) 22041163; 22041164

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Bioactivity Pharmacological Data (11) 1 of 11

Comment (Pharmacological Data)

Bioactivities present

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Rothman, Richard B.; Baumann, Michael H.

Current Topics in Medicinal Chemistry, 2006 , vol. 6, # 17 p. 1845 - 1859 Title/Abstract Full Text View citing articles Show Details

2 of 11

Effect (Pharmacological Data)

dopamine (DA); release of

Species or TestSystem (Pharmacological Data)

caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1457 nmol/l

Location

Page/Page column 81-83

Reference

Bruce E.; ROTHMAN, Richard; LANDAVAZO, Antonio; PAGE, Kevin M.; DECKER, Ann Marie

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

3 of 11

Effect (Pharmacological Data)

serotonin (5-HT); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Location

Page/Page column 81-83

Comment (Pharmacological Data)

No effect

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

4 of 11

Effect (Pharmacological Data)

norepinephrine (NE); release of

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

349 nmol/l

Location

Page/Page column 81-83

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

5 of 11

Effect (Pharmacological Data)

serotonin (5-HT2B) receptor; agonist

Species or TestSystem (Pharmacological Data)

whole brain minus cerebellum and caudate of rat

Method (Pharmacological Data)

Location

Page/Page column 81-83

Comment (Pharmacological Data)

No effect

Reference

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

6 of 11

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT re-uptake performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

7 of 11

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>5-HT release performed in presence of nomifensine (100 nmol/l) and GBR12935

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

8 of 11

9 of 11

> 100000 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

<3H>norepinephrine release performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

349 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat whole brain minus caudate synaptosomes

Sex

male

Method (Pharmacological Data)

10 of 11

11 of 11

Further Details (Pharmacological Data)

<3H>norepinephrine re-uptake performed in presence of 3β-(4-iodophenyl)-tropane-2β-pyrrolidine carboxamide tartarate

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

270 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Further Details (Pharmacological Data)

references: (+)-methamphetamine, indatraline; further study with indatraline

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

1457 nmol/l

Results

indatraline reversed the releasing effect of title comp.; diagram

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transport; inhibition of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat caudate synaptosomes

Sex

male

Method (Pharmacological Data)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3320 nmol/l

Reference

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European Journal of Pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Chemical Name: phenmetrazine hydrochloride Reaxys Registry Number: 4159908

CAS Registry Number: 1707-14-8 Type of Substance: heterocyclic Molecular Formula: C11H15NO*ClH

3 prep out of 12 reactions.

Identification Physical Data (3) Spectra (1) Bioactivity (2)

Linear Structure Formula: C11H15NO*ClH Molecular Weight: 213.707

InChI Key: VJNXVAVKCZJOFQ-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms phenmetrazine hydrochloride, 3-methyl-2-phenyl-morpholine; hydrochloride, 3-Methyl-2-phenyl-morpholin; Hydrochlorid, Preludin Identification Patent-Specific Data (1) Location in Patent

Reference

Claim

General Mills, Inc.

Patent: US2002/44968 A1, 2002 ; Title/Abstract Full Text Show Details

Alza Corporation

Patent: US5023088 A1, 1991 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (2) Melting Point

Reference

174 - 177 °C

Kuhnert-Brandstaetter et al.

Scientia Pharmaceutica, 1964 , vol. 32, p. 308,310,320 Full Text Show Details

180 - 182 °C

Klosa,J.

Journal fuer Praktische Chemie (Leipzig), 1963 , vol. 21, p. 12 - 17 Full Text View citing articles Show Details

Shozokitagawa

Patent: JP623579 , 1962 ; Chem.Abstr., 1963 , vol. 58, # 9092h Full Text Show Details

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

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

21.5 deg

589 nm

20 °C

Reference Spofa,Sdruzeni Podniku Pro Zdravotnickou Vyrobu;

Patent: GB899386 , 1959 ; Chem.Abstr., 1963 , vol. 58, # 6838e Full Text Show Details

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

Solvent (UV/VIS Spectroscopy)

Comment (UV/VIS Spectroscopy)

Reference

Spectrum

H2O

220 - 270 nm

Haag

Dtsch. Apothg.-Ztg., 1957 , vol. 97, p. Spl. S. 5 Full Text Show Details

Bioactivity Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Maurich; Rubessa

Bollettino Chimico Farmaceutico, 1973 , vol. 112, # 7 p. 465 - 471 Title/Abstract Full Text View citing articles Show Details

Avramova; Dryanovska; Ilarionov

Pharmazie, 1977 , vol. 32, # 10 p. 575 - 577 Title/Abstract Full Text View citing articles Show Details

General Mills, Inc.

Patent: US2002/44968 A1, 2002 ; Title/Abstract Full Text Show Details

Klosa,J.

Journal fuer Praktische Chemie (Leipzig), 1963 , vol. 21, p. 12 - 17 Full Text View citing articles Show Details

Haag

Dtsch. Apothg.-Ztg., 1957 , vol. 97, p. Spl. S. 5 Full Text Show Details

Kuhnert-Brandstaetter et al.

Scientia Pharmaceutica, 1964 , vol. 32, p. 308,310,320 Full Text Show Details

Spofa,Sdruzeni Podniku Pro Zdravotnickou Vyrobu;

Patent: GB899386 , 1959 ; Chem.Abstr., 1963 , vol. 58, # 6838e Full Text Show Details

Shozokitagawa

Patent: JP623579 , 1962 ; Chem.Abstr., 1963 , vol. 58, # 9092h Full Text Show Details

BEHRENDT; DEININGER

Arzneimittel-Forschung, 1963 , vol. 13, p. 711 - 716 Title/Abstract Full Text View citing articles Show Details

Avramova, Petya; Danchev, Nicolai; Buyukliev, Rossen; Bogoslovova, Tatiana

Archiv der Pharmazie, 1998 , vol. 331, # 11 p. 342 - 346 Title/Abstract Full Text View citing articles Show Details

Alza Corporation

Patent: US5023088 A1, 1991 ; Title/Abstract Full Text Show Details

Aeberli; Eden; Gogerty; Houlihan; Penberthy

Journal of Medicinal Chemistry, 1975 , vol. 18, # 2 p. 177 - 182 Title/Abstract Full Text Show Details

Faraj; Israili; Kight; Smissman; Pazdernik

Journal of medicinal chemistry, 1976 , vol. 19, # 1 p. 20 - 25 Title/Abstract Full Text Show Details

Rothman, Richard B; Katsnelson, Marina; Vu, Nga; Partilla, John S; Dersch, Christina M; Blough, Bruce E; Baumann, Michael H

European journal of pharmacology, 2002 , vol. 447, # 1 p. 51 - 57 Title/Abstract Full Text Show Details

Freter; Goetz; Oliver

Journal of medicinal chemistry, 1970 , vol. 13, # 6 p. 1228 - 1230 Title/Abstract Full Text Show Details

HOLLAND; BUCK; WEISSMAN

Journal of medicinal chemistry, 1963 , vol. 6, p. 519 - 524 Title/Abstract Full Text Show Details

KNAPP

Journal of medicinal chemistry, 1964 , vol. 7, p. 433 - 439 Title/Abstract Full Text View citing articles Show Details

Donald R.Gehlert; David J. Goldstein; Philip A. Hipskind

Annual reports in medicinal chemistry, 1996 , vol. 31, p. 201 - 210 Title/Abstract Full Text Show Details

Frank P. Palopoli

Annual reports in medicinal chemistry, 1969 , vol. 5, p. 40 - 48 Title/Abstract Full Text Show Details

Frank P. Palopoli

Annual reports in medicinal chemistry, 1967 , vol. 3, p. 47 - 52 Title/Abstract Full Text Show Details

2 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Acta pharmaceutica Suecica, 1967 , vol. 4, p. 37 Full Text Show Details

JOHN KRAPCHO; JOHN P. HIGH

Journal of medicinal chemistry, 1967 , vol. 10, # 3 p. 495 - 497 Title/Abstract Full Text Show Details

National Technical Information Service, AD277-689., vol. AD277-689

Full Text Show Details

Clarke's Analysis of Drugs and Poisons Full Text Show Details

Toxicology and applied pharmacology, 1960 , vol. 2, p. 589 Full Text Show Details

Psychotropic Drugs and Related Compounds, 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972, 286., 1972 , p. 286 Full Text Show Details

Allain, Florence; Minogianis, Ellie-Anna; Roberts, David C.S.; Samaha, Anne-Noël

Neuroscience and Biobehavioral Reviews, 2015 , vol. 56, p. 166 - 179 Title/Abstract Full Text View citing articles Show Details

Beharry, Shruti; Gibbons, Simon

Forensic Science International, 2016 , vol. 267, p. 25 - 34 Title/Abstract Full Text View citing articles Show Details

Bäckberg, Matilda; Westerbergh, Jenny; Beck, Olof; Helander, Anders

Clinical Toxicology, 2016 , vol. 54, # 9 p. 819 - 825 Title/Abstract Full Text View citing articles Show Details

McLaughlin, Gavin; Morris, Noreen; Kavanagh, Pierce V.; Dowling, Geraldine; Power, John D.; Twamley, Brendan; O'Brien, John; Talbot, Brian; Sitte, Harald H.; Brandt, Simon D.

Drug Testing and Analysis, 2017 , vol. 9, # 3 p. 369 - 377 Title/Abstract Full Text Show Details

Reaxys Registry Number: 4159909

CAS Registry Number: 1707-14-8, 13580-35-3, 13850-47-0, 6397149-3 Type of Substance: heterocyclic Molecular Formula: C11H15NO*ClH Linear Structure Formula: C11H15NO*ClH Molecular Weight: 213.707

InChI Key: VJNXVAVKCZJOFQ-INDIWFAOSA-N

no reactions.

Physical Data (1)

1 prep out of 1 reactions.

Identification Physical Data (1)

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Physical Data Melting Point (1) Melting Point

Reference

176 - 178.6 °C

Geigy Chem.

Patent: US3282936 , 1966 ; Chem.Abstr., vol. 66, # 65485 Full Text Show Details

Chemical Name: trans-2-Phenyl-3-methylmorpholin-hydrochlorid Reaxys Registry Number: 4159910

CAS Registry Number: 1707-14-8, 13580-35-3, 13850-47-0, 6397149-3 Type of Substance: heterocyclic Molecular Formula: C11H15NO*ClH Linear Structure Formula: C11H15NO*ClH Molecular Weight: 213.707

InChI Key: VJNXVAVKCZJOFQ-QLSWKGBWSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms trans-2-Phenyl-3-methylmorpholin-hydrochlorid Identification Substance Label (1)

Label

Reference

C.H.Boehringer Sohn Patent: FR1397563 , 1963 ; Chem.Abstr., 1965 , vol. 63, # 4308de Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

176 - 178.6 °C

C.H.Boehringer Sohn Patent: FR1397563 , 1963 ; Chem.Abstr., 1965 , vol. 63, # 4308de Full Text Show Details

Reaxys Registry Number: 4058051

CAS Registry Number: 62265-29-6 Type of Substance: heterocyclic Molecular Formula: C11H15NO*H2O4S Linear Structure Formula: C11H15NO*H2O4S Molecular Weight: 275.326

InChI Key: ZUZZYILKYYTIIA-UHFFFAOYSA-N

no reactions.

Physical Data (1)

Identification Physical Data (1)

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Physical Data Further Information (1) Description (Further Information)

Reference

Further information

Shozokitagawa

Patent: JP623579 , 1962 ; Chem.Abstr., 1963 , vol. 58, # 9092h Full Text Show Details

Chemical Name: Phenmetracin-diliturat Reaxys Registry Number: 4092180

CAS Registry Number: 88154-31-8 Type of Substance: heterocyclic Molecular Formula: C4H3N3O5*C11H15NO Linear Structure Formula: C11H15NO*C4H3N3O5

Molecular Weight: 350.331

InChI Key: HTDSHLCHFCELPK-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms Phenmetracin-diliturat Identification Substance Label (1)

no reactions.

Label

Reference

Kuhnert-Brandstaetter et al.

Pharmaceutica Acta Helvetiae, 1975 , vol. 50, p. 360,364 Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

266 - 270 °C

Kuhnert-Brandstaetter et al.

Pharmaceutica Acta Helvetiae, 1975 , vol. 50, p. 360,364 Full Text Show Details

Chemical Name: 8-Chlor-theophyllin

no reactions.

Identification Physical Data (2)

Reaxys Registry Number: 4120456

Type of Substance: heterocyclic Molecular Formula: C8H9ClN4O2*C11H15NO Linear Structure Formula: C11H15NO*C8H9ClN4O2

Molecular Weight: 405.884

InChI Key: IGNMIGLDOJWDET-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms 8-Chlor-theophyllin Identification Substance Label (1) Label

Reference

Chem,Fabrik Ravensberg GmbH,

Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

128 °C

Chem,Fabrik Ravensberg GmbH,

Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

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

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

9.9 deg

589 nm

18 °C

Reaxys Registry Number: 22041315

Reference Chem,Fabrik Ravensberg GmbH,

Patent: US3018222 , 1956 ; Chem.Abstr., 1963 , vol. 58, # 6840c Full Text Show Details

2 prep

Identification

Molecular Formula: C4H4O4*2C11H15NO Linear Structure Formula: C4H4O4*2C11H15NO Molecular Weight: 470.566

InChI Key: KLHYTFFPRLSLKO-WLHGVMLRSA-N

out of 2 reactions.

Spectra (1)

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Identification Patent-Specific Data (1) Related Markush Structure (RN)

Reference

22041163; 22041164

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details

Spectra NMR Spectroscopy (1) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

300 MHz

Original Text (NMR Spectroscopy)

Location

1H NMR (300 MHz, MeOH) δ ppm 1.01 (d, J=6.78 Hz, 3 H) 3.20 - 3.41 (m, 3 H) 3.84 - 3.99 (m, 1 H) 4.13 (d, J=l 4.32 Hz, 1 H) 4.32 (d, J=10.17 Hz, 1 H) 6.70 (s, 1 H) 7.39 (s, 5 H).

Page/Page column 55

Comment (NMR Spectroscopy) Signals given

Patent: WO2011/146850 A1, 2011 ; Title/Abstract Full Text Show Details