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

Molecular Formula	C11H15NO
Molecular Weight	177.2429
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 Later on the drug was withdrawn from the market due to the reported cases of abuse.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 41 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 8504	7765.0 nM [EC50]
Sodium-dependent dopamine transporter 43 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 8504	131.0 nM [EC50]
Sodium-dependent noradrenaline transporter 39 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 8504	50.4 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Obesity 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13383418	Primary		Approved 8583	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
Selective suppression of cocaine- versus food-maintained responding by monoamine releasers in rhesus monkeys: benzylpiperazine, (+)phenmetrazine, and 4-benzylpiperidine.	2009-04	19151247
Nontraumatic rhabdomyolysis and acute renal failure associated with oral phenmetrazine hydrochloride.	1984-02	6727334
Rhabdomyolysis and shock after intravenous amphetamine administration.	1977-04	848798
[Psychotic syndromes in phenmetrazine addiction].	1972-01-15	5061103
[Psychoses induced by chronic administration of barbiturates in combination with phenmetrazine].	1971-10	5119297
[Mental disorders caused by phenmetrazine abuse].	1970-01-01	5421201
[Psychoses induced by phenmetrazine].	1969-07-01	5356063

Patents

Sample Use Guides

In Vivo Use Guide

Maximum dose is 75 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:18 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:18 GMT 2025`
Record UNII	XA501VL3VR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENMETRAZINE [HSDB]

Preferred Name

English

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

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

Systematic Name

English

PHENMETRAZINE [VANDF]

Common Name

English

Classification Tree Code System Code

DEA NO.

1631