4-Hydroxy-3-methoxymethamphetamine

4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA).^[1][2][3] It is a slightly more potent stimulant than MDMA in rodents.^[4] The drug is substantially less potent than MDMA as a monoamine releasing agent in vitro.^[5][6] 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).^[5][6] The predicted log P of HMMA is 1.2.^[7]

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 Y
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

See also

• 4-Hydroxy-3-methoxyamphetamine (HMA)
• 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine)
• 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine)
• 2,4,5-Trihydroxyamphetamine (THA)
• 2,4,5-Trihydroxymethamphetamine (THMA)
• 3,4-Dihydroxymethcathinone (HHMC)
• 4-Hydroxy-3-methoxymethcathinone (HMMC)