3,4-Dihydroxymethamphetamine

3,4-Dihydroxymethamphetamine
Clinical data
Other names	HHMA; 3,4-DHMA; Di-OH-MA; α-Methylepinine; α,N-Dimethyldopamine; α-Methyl-N-methyldopamine; 3,4-Dihydroxy-N-methylamphetamine
Identifiers
	IUPAC name 4-[2-(methylamino)propyl]benzene-1,2-diol;
CAS Number	15398-87-5;
PubChem CID	161126;
ChemSpider	141547;
UNII	VFV03WN1VN;
CompTox Dashboard (EPA)	DTXSID90934885 ;
Chemical and physical data
Formula	C10H15NO2
Molar mass	181.235 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1)O)O)NC;
	InChI InChI=1S/C10H15NO2/c1-7(11-2)5-8-3-4-9(12)10(13)6-8/h3-4,6-7,11-13H,5H2,1-2H3; Key:NTCPGTZTPGFNOM-UHFFFAOYSA-N;

3,4-Dihydroxymethamphetamine (HHMA, 3,4-DHMA), or 3,4-dihydroxy-N-methylamphetamine, also known as α-methylepinine or α,N-dimethyldopamine, is the major metabolite of 3,4-methylenedioxy-N-methylamphetamine (MDMA). It is formed from MDMA by O-demethylation via cytochrome P450 enzymes including CYP2D6 as well as CYP1A2 and CYP3A4. Like MDMA, HHMA is a monoamine releasing agent.

Along with 3,4-dihydroxyamphetamine (HHA; α-methyldopamine), HHMA may be involved in the serotonergic neurotoxicity of MDMA. However, findings in this regard are conflicting, and the neurotoxicity of MDMA and related agents may instead be based on their mechanism of action without involvement of metabolites.