4-Hydroxy-3-methoxyamphetamine

4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-O-methyl-α-methyldopamine, is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA).^[1][2][3] It is substantially less potent than MDMA or 3,4-methylenedioxyamphetamine (MDA) as a monoamine releasing agent in vitro.^[4][5] Nonetheless, HMA has been found to induce the release of serotonin, norepinephrine, and dopamine with EC₅₀Tooltip half-maximal effective concentration values of 897 nM, 694 nM, and 1450–3423 nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA).^[4][5] The predicted log P of HMA is 0.6.^[6]

4-Hydroxy-3-methoxyamphetamine

Clinical data
Other names	HMA; 3-Methoxy-4-hydroxyamphetamine; MHA; 3-O-Methyl-α-methyldopamine
Drug class	Serotonin–norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 4-(2-aminopropyl)-2-methoxyphenol
CAS Number	13026-44-3
PubChem CID	197139
ChemSpider	170725
UNII	UW5V6G007J
ChEBI	CHEBI:173516
ChEMBL	ChEMBL1347
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)OC)N
InChI InChI=1S/C10H15NO2/c1-7(11)5-8-3-4-9(12)10(6-8)13-2/h3-4,6-7,12H,5,11H2,1-2H3 Key:GPBOYXOSSQEJBH-UHFFFAOYSA-N

See also

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