PHENMETRAZINE

First approved in 1956

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H15NO
Molecular Weight	177.2429
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1NCCO[C@H]1C2=CC=CC=C2

InChI

InChIKey=OOBHFESNSZDWIU-GXSJLCMTSA-N

InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3/t9-,11+/m0/s1

HIDE SMILES / InChI

Description
Sources: http://journals.sagepub.com/doi/pdf/10.1177/006947706700500107 | https://www.ncbi.nlm.nih.gov/pubmed/17017961 | ISBN-13: 978-0876308165, Klein D., Rowland L., 'Current Psychotherapeutic Drugs' (1996), Retrieved from https://books.google.com/books?id=rc9mVkQbJlMC&dq

Phenmetrazine is an anti-obesity drug, which was discovered by Boehringer-Ingelheim in 1952 and approved by FDA under the name Preludin. Later on the drug was withdrawn from the market due to the reported cases of abuse. According to some studies, misuse of phenmetrazine turned many young addicts to crime. It is suggested that the drug exerts its effect by inhibiting the monoamine transport.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium-dependent serotonin transporter 40 Target ID: P31645 Gene ID: 6532.0 Gene Symbol: SLC6A4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17017961	Inhibitor 8297	7765.0 nM [EC50]
Sodium-dependent dopamine transporter 42 Target ID: Q01959 Gene ID: 6531.0 Gene Symbol: SLC6A3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17017961	Inhibitor 8297	131.0 nM [EC50]
Sodium-dependent noradrenaline transporter 38 Target ID: P23975 Gene ID: 6530.0 Gene Symbol: SLC6A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17017961	Inhibitor 8297	50.4 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13383418	Primary		Approved 8429	Unknown Approved Use Treatment of obesity.

C_max

Value	Dose	Co-administered	Analyte	Population
120 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6026786/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENMETRAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6026786/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		PHENMETRAZINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

PubMed

Title	Date	PubMed
[Psychoses induced by phenmetrazine].	1969 Jul-Aug	5356063
[Mental disorders caused by phenmetrazine abuse].	1970 Jan-Feb	5421201
Rhabdomyolysis and shock after intravenous amphetamine administration.	1977 Apr	848798
Nontraumatic rhabdomyolysis and acute renal failure associated with oral phenmetrazine hydrochloride.	1984 Feb	6727334

Patents

Sample Use Guides

In Vivo Use Guide

Maximum dose is 75 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

PHENMETRAZINE

Official Name

English

3-METHYL-2-PHENYLMORPHOLINE

Systematic Name

English

Phenmetrazine [WHO-DD]

Common Name

English

phenmetrazine [INN]

Common Name

English

MORPHOLINE, 3-METHYL-2-PHENYL-, (2R,3R)-REL-

Systematic Name

English

PHENMETRAZINE [MI]

Common Name

English

MORPHOLINE, 3-METHYL-2-PHENYL-

Systematic Name

English

TRANS-PHENMETRAZINE

Common Name

English

PHENMETRAZINE [HSDB]

Common Name

English

MORPHOLINE, 3-METHYL-2-PHENYL-, TRANS-

Systematic Name

English

PHENMETRAZINE [VANDF]

Common Name

English

Classification Tree Code System Code

DEA NO.

1631