4-Hydroxy-3-methoxymethamphetamine

4-Hydroxy-3-methoxymethamphetamine
Clinical data
Other names	HMMA; 4-Hydroxy-3-methoxy-N-methylamphetamine; 3-Methoxy-4-hydroxymethamphetamine; 3-Methoxy-4-hydroxy-N-methylamphetamine
Drug class	Serotonin–norepinephrine–dopamine releasing agent
Identifiers
	IUPAC name 2-methoxy-4-[2-(methylamino)propyl]phenol;
CAS Number	117652-28-5 ;
PubChem CID	3081137;
ChemSpider	2338803;
UNII	RBY3J6H4JW;
CompTox Dashboard (EPA)	DTXSID70922503 ;
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1)O)OC)NC;
	InChI InChI=1S/C11H17NO2/c1-8(12-2)6-9-4-5-10(13)11(7-9)14-3/h4-5,7-8,12-13H,6H2,1-3H3; Key:UVDWYWYWOMOEFX-UHFFFAOYSA-N;

4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasing agent in vitro. Nonetheless, HMMA has been found to induce the release of serotonin, norepinephrine, and dopamine with EC₅₀Tooltip half-maximal effective concentration values of 589 nM, 625 nM, and 607–2884 nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA). The predicted log P of HMMA is 1.2.