4-Hydroxy-3-methoxymethcathinone

4-Hydroxy-3-methoxymethcathinone (HMMC), or 3-methoxy-4-hydroxy-N-methylcathinone, is a monoamine releasing agent of the amphetamine and cathinone families.^[1][2][3] It is an active metabolite of methylone (3,4-methylenedioxymethcathinone; MDMC).^[1][2][3] The drug is a very low-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA), with EC₅₀Tooltip half-maximal effective concentration values of 7,210 nM for serotonin, 6,340 nM for norepinephrine, and 5,840 nM for dopamine in rat brain synaptosomes.^[1][2] HMMC was first described in the scientific literature by 2011.^[3][1][2]

4-Hydroxy-3-methoxymethcathinone

Clinical data
Other names	4-Hydroxy-3-methoxymethcathinone; HMMC; 3-Methoxy-4-hydroxymethcathinone; Hydroxymethoxymethcathinone; 3-Methoxy-4-hydroxy-N-methylcathinone; 4-Hydroxy-3-methoxy-N-methylcathinone; 3MeO,4HO-MC; MHMC; Methylone-M1; 4′-Hydroxy-3′-methoxy-2-(isopropylamino)propanophenone
Identifiers
IUPAC name 1-(4-hydroxy-3-methoxyphenyl)-2-(methylamino)propan-1-one
CAS Number	916177-15-6
PubChem CID	71422851
ChemSpider	28552464
UNII	FJ267O4DJ1
CompTox Dashboard (EPA)	DTXSID10841825
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(=O)C1=CC(=C(C=C1)O)OC)NC
InChI InChI=1S/C11H15NO3/c1-7(12-2)11(14)8-4-5-9(13)10(6-8)15-3/h4-7,12-13H,1-3H3 Key:GIQCAMWUCKLMPC-UHFFFAOYSA-N

See also

• 3,4-Dihydroxymethcathinone (HHMC; 3,4-DHMC)
• 4-Hydroxy-3-methoxyamphetamine (HMA)
• 4-Hydroxy-3-methoxymethamphetamine (HMMA)
• α-Methyldopamine (3,4-dihydroxyamphetamine; HHA; 3,4-DHA)
• α-Methylepinine (3,4-dihydroxymethamphetamine; HHMA, 3,4-DHMA)