U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of PHENMETRAZINE

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 Later on the drug was withdrawn from the market due to the reported cases of abuse.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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P31645
Gene ID: 6532.0
Gene Symbol: SLC6A4
Target Organism: Homo sapiens (Human)
7765.0 nM [EC50]
Target ID: Q01959
Gene ID: 6531.0
Gene Symbol: SLC6A3
Target Organism: Homo sapiens (Human)
131.0 nM [EC50]
Target ID: P23975
Gene ID: 6530.0
Gene Symbol: SLC6A2
Target Organism: Homo sapiens (Human)
50.4 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Treatment of obesity.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
120 μg/L
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
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
Patents

Sample Use Guides

In Vitro Use Guide
Unknown
Name Type Language
PHENMETRAZINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
NCI_THESAURUS C29728
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
Code System Code Type Description
CHEBI
8067
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
WIKIPEDIA
PHENMETRAZINE
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
FDA UNII
XA501VL3VR
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
SMS_ID
100000082257
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
CAS
1618-50-4
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
NCI_THESAURUS
C66372
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
PUBCHEM
12314141
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PRIMARY
EVMPD
SUB09769MIG
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-143-4
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
INN
553
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
HSDB
3156
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID5023455
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PRIMARY
DRUG CENTRAL
2133
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PRIMARY
RXCUI
8133
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201208
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
MESH
D010633
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY
MERCK INDEX
m8621
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY Merck Index
CAS
134-49-6
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB00830
Created by admin on Fri Dec 15 15:28:27 GMT 2023 , Edited by admin on Fri Dec 15 15:28:27 GMT 2023
PRIMARY