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

Details

Stereochemistry ABSOLUTE
Molecular Formula C11H17N
Molecular Weight 163.2594
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETAMFETAMINE

SMILES

C[C@@H](CC1=CC=CC=C1)N(C)C

InChI

InChIKey=OBDSVYOSYSKVMX-JTQLQIEISA-N
InChI=1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3/t10-/m0/s1

HIDE SMILES / InChI
Dimetamfetamine is the N-methylated analog of methamphetamine, produces behavioral effects that are generally comparable to those of methamphetamine, but with reduced potency. It is often found as an impurity in preparations of methamphetamine. Dimetamfetamine itself is less neurotoxic than methamphetamine. Dimetamfetamine is metabolized to p-hydroxyl methamphetamine, p-hydroxyl dimetamfetamine, amphetamine, methamphetamine, and N,N-dimethylamphetamine N-oxide in humans, and flavin-containing monooxygenase-1 and CYP2D6 are mainly involved in the N-oxidation and N-demethylation of dimetamfetamine, respectively. Dimetamfetamine has also been used illegally in Korea, and the Korean government placed DMA on the official list of controlled substances on December 4, 2006.

Approval Year

PubMed

PubMed

TitleDatePubMed
Stereoselectivity in the cytochrome P450-dependent N-demethylation and flavin monooxygenase-dependent N-oxidation of N,N-dimethylamphetamine.
2013-11
Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs.
1997-12
N-methylation dissociates methamphetamine's neurotoxic and behavioral pharmacologic effects.
1997-10-10
Reinforcing effects of enantiomers of N,N-dimethylamphetamine in squirrel monkeys.
1992
Isomeric amphetamines--a problem for urinalysis?
1991-09
Development of monoclonal antibodies reactive with methamphetamine raised against a new antigen.
1991
Patents

Sample Use Guides

100 mg/kg every 6 h x 5
Route of Administration: Other
Name Type Language
DIMETAMFETAMINE [MART.]
Preferred Name English
DIMETAMFETAMINE
INN   MART.   WHO-DD  
INN  
Official Name English
dimetamfetamine [INN]
Common Name English
Dimetamfetamine [WHO-DD]
Common Name English
(S)-N,N,.ALPHA.-TRIMETHYLPHENETHYLAMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL2106635
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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NCI_THESAURUS
C65402
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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MESH
C003714
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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SMS_ID
100000082660
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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FDA UNII
92M4C245D1
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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CAS
17279-39-9
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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PUBCHEM
65682
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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INN
4305
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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EVMPD
SUB07169MIG
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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ECHA (EC/EINECS)
241-311-3
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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EPA CompTox
DTXSID5046146
Created by admin on Wed Apr 02 08:24:11 GMT 2025 , Edited by admin on Wed Apr 02 08:24:11 GMT 2025
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