4-Hydroxy-3-methoxyamphetamine explained

Class:	Serotonin–norepinephrine–dopamine releasing agent
Cas Number:	13026-44-3
Pubchem:	197139
Chemspiderid:	170725
Unii:	UW5V6G007J
Chebi:	173516
Chembl:	1347
Synonyms:	HMA; 3-Methoxy-4-hydroxyamphetamine; 3-O-Methyl-α-methyldopamine
Iupac Name:	4-(2-aminopropyl)-2-methoxyphenol
C:	10
H:	15
N:	1
O:	2
Smiles:	CC(CC1=CC(=C(C=C1)O)OC)N
Stdinchi:	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
Stdinchikey:	GPBOYXOSSQEJBH-UHFFFAOYSA-N

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 values of 897nM, 694nM, and 1450–3423nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA). The predicted log P of HMA is 0.6.^[6]

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)

Notes and References

1. de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, Segura J, Camí J . Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition . Therapeutic Drug Monitoring . 26 . 2 . 137–144 . April 2004 . 15228154 . 10.1097/00007691-200404000-00009 .
2. Rietjens SJ, Hondebrink L, Westerink RH, Meulenbelt J . Pharmacokinetics and pharmacodynamics of 3,4-methylenedioxymethamphetamine (MDMA): interindividual differences due to polymorphisms and drug-drug interactions . Critical Reviews in Toxicology . 42 . 10 . 854–876 . November 2012 . 23030234 . 10.3109/10408444.2012.725029 .
3. Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME . Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems . Journal of Psychopharmacology . 33 . 7 . 831–841 . July 2019 . 31038382 . 10.1177/0269881119844185 . 8269116 .
4. Book: Blough B . Dopamine-releasing agents . Dopamine Transporters: Chemistry, Biology and Pharmacology . 305–320 . July 2008 . 978-0-470-11790-3 . Wiley . Hoboken [NJ] . https://archive.org/details/dopaminetranspor0000unse/page/310/ . https://archive.today/20241104022653/https://archive.org/details/dopaminetranspor0000unse/page/310/mode/2up . 4 November 2024 . TABLE 11-2 Comparison of the DAT- and NET-Releasing Activity of a Series of Amphetamines [...].
5. Yubero-Lahoz S, Ayestas MA, Blough BE, Partilla JS, Rothman RB, de la Torre R, Baumann MH . Effects of MDMA and related analogs on plasma 5-HT: relevance to 5-HT transporters in blood and brain . European Journal of Pharmacology . 674 . 2–3 . 337–344 . January 2012 . 22079770 . 3253888 . 10.1016/j.ejphar.2011.10.033 .
6. Web site: 3-O-Methyl-Alpha-Methyldopamine . PubChem . U.S. National Library of Medicine . 14 November 2024.