Dimethylamphetamine

Dimethylamphetamine (Metrotonin), also known as dimetamfetamine (INN), dimephenopan and N,N-dimethylamphetamine, is a stimulant drug of the phenethylamine and amphetamine chemical classes. Dimethylamphetamine has weaker stimulant effects than amphetamine or methamphetamine and is considerably less addictive^[1] and less neurotoxic compared to methamphetamine.^[2][3] However, it still retains some mild stimulant effects and abuse potential,^[4] and is illegal in both the United States and Australia.

Routes of
administrationOral

ATC code

• none

Legal status

• AU: S9 (Prohibited substance)
• US: Schedule I

CAS Number

• 4075-96-1 ^Y

Quick facts Clinical data, Routes ofadministration ...

Dimethylamphetamine
INN: Dimetamfetamine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) US: Schedule I
Identifiers
IUPAC name N,N-dimethyl-1-phenylpropan-2-amine
CAS Number	4075-96-1 Y
PubChem CID	20006
ChemSpider	18847 N
UNII	IYE3F3MHCU
KEGG	C22825 Y
CompTox Dashboard (EPA)	DTXSID40860201
Chemical and physical data
Formula	C11H17N
Molar mass	163.264 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(N(C)C)CC1=CC=CC=C1
InChI InChI=1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3 Y Key:OBDSVYOSYSKVMX-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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Dimethylamphetamine has occasionally been found in illicit methamphetamine laboratories, but is usually an impurity rather than the desired product. It may be produced by accident when methamphetamine is synthesised by N-methylation of dextroamphetamine if the reaction temperature is too high or an excess of methylating agent is used.^[5][6]

It is said to be a prodrug of methamphetamine and amphetamine, which are minor metabolites.^[7][8][9]