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Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO.ClH
Molecular Weight 213.704
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENMETRAZINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=VJNXVAVKCZJOFQ-XQKZEKTMSA-N
InChI=1S/C11H15NO.ClH/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10;/h2-6,9,11-12H,7-8H2,1H3;1H/t9-,11+;/m1./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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 Later on the drug was withdrawn from the market due to the reported cases of abuse.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

1956
94
Targets

Targets

Primary TargetPharmacologyConditionPotency
Sodium-dependent serotonin transporter
40
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
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)
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)
Inhibitor
8297
 50.4 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Unknown

Approved Use

Treatment of obesity.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

PubMed

TitleDatePubMed
[Psychoses induced by phenmetrazine].
1969 Jul-Aug
[Mental disorders caused by phenmetrazine abuse].
1970 Jan-Feb
[Psychoses induced by chronic administration of barbiturates in combination with phenmetrazine].
1971 Oct
[Psychotic syndromes in phenmetrazine addiction].
1972 Jan 15
Rhabdomyolysis and shock after intravenous amphetamine administration.
1977 Apr
Nontraumatic rhabdomyolysis and acute renal failure associated with oral phenmetrazine hydrochloride.
1984 Feb
Selective suppression of cocaine- versus food-maintained responding by monoamine releasers in rhesus monkeys: benzylpiperazine, (+)phenmetrazine, and 4-benzylpiperidine.
2009 Apr
Patents

Patents

GB19530018247
2
US2835669
2

Sample Use Guides

In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:20:17 UTC 2023
Edited
by admin
on Fri Dec 15 16:20:17 UTC 2023
Record UNII
6U85YRT588
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENMETRAZINE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
Common Name English
Phenmetrazine hydrochloride [WHO-DD]
Common Name English
MORPHOLINE, 3-METHYL-2-PHENYL-, HYDROCHLORIDE
Systematic Name English
PHENMETRAZINE HYDROCHLORIDE [VANDF]
Common Name English
PRELUDIN
Brand Name English
PHENMETRAZINE HCL
Common Name English
PHENMETRAZINE HYDROCHLORIDE [MI]
Common Name English
PHENMETRAZINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PHENMETRAZINE HYDROCHLORIDE [MART.]
Common Name English
3-Methyl-2-phenylmorpholine hydrochloride
Systematic Name English
MORPHOLINE, 3-METHYL-2-PHENYL-, HYDROCHLORIDE, TRANS-
Systematic Name English
NSC-405728
Code English
Classification Tree Code System Code
DEA NO. 1631
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
NCI_THESAURUS C29728
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
Code System Code Type Description
NSC
405728
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
PUBCHEM
92159
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
CAS
13580-35-3
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
DRUG BANK
DBSALT000705
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
MERCK INDEX
m8621
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY Merck Index
SMS_ID
100000085273
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
CAS
1707-14-8
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
NCI_THESAURUS
C66373
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
216-950-6
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
RXCUI
203198
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201208
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
EPA CompTox
DTXSID0047822
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
FDA UNII
6U85YRT588
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
EVMPD
SUB03750MIG
Created by admin on Fri Dec 15 16:20:17 UTC 2023 , Edited by admin on Fri Dec 15 16:20:17 UTC 2023
PRIMARY
Related Record Type Details
Structure of PHENMETRAZINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PHENMETRAZINE
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