4-Hydroxy-3-methoxyamphetamine

{{Short description|MDMA metabolite}}

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| image = 4-Hydroxy-3-methoxyamphetamine.svg

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| class = Serotonin–norepinephrine–dopamine releasing agent

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| CAS_number = 13026-44-3

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| PubChem = 197139

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| ChemSpiderID = 170725

| UNII = UW5V6G007J

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| ChEBI = 173516

| ChEMBL = 1347

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| synonyms = HMA; 3-Methoxy-4-hydroxyamphetamine; MHA; 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).{{cite journal | vauthors = de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, Segura J, Camí J | title = Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition | journal = Therapeutic Drug Monitoring | volume = 26 | issue = 2 | pages = 137–144 | date = April 2004 | pmid = 15228154 | doi = 10.1097/00007691-200404000-00009 }}{{cite journal | vauthors = Rietjens SJ, Hondebrink L, Westerink RH, Meulenbelt J | title = Pharmacokinetics and pharmacodynamics of 3,4-methylenedioxymethamphetamine (MDMA): interindividual differences due to polymorphisms and drug-drug interactions | journal = Critical Reviews in Toxicology | volume = 42 | issue = 10 | pages = 854–876 | date = November 2012 | pmid = 23030234 | doi = 10.3109/10408444.2012.725029 }}{{cite journal | vauthors = Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME | title = Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems | journal = Journal of Psychopharmacology | volume = 33 | issue = 7 | pages = 831–841 | date = July 2019 | pmid = 31038382 | doi = 10.1177/0269881119844185 | pmc = 8269116 }} It is substantially less potent than MDMA or 3,4-methylenedioxyamphetamine (MDA) as a monoamine releasing agent in vitro.{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}{{cite journal | vauthors = Yubero-Lahoz S, Ayestas MA, Blough BE, Partilla JS, Rothman RB, de la Torre R, Baumann MH | title = Effects of MDMA and related analogs on plasma 5-HT: relevance to 5-HT transporters in blood and brain | journal = European Journal of Pharmacology | volume = 674 | issue = 2–3 | pages = 337–344 | date = January 2012 | pmid = 22079770 | pmc = 3253888 | doi = 10.1016/j.ejphar.2011.10.033 }} Nonetheless, HMA has been found to induce the release of serotonin, norepinephrine, and dopamine with {{Abbrlink|EC₅₀|half-maximal effective concentration}} values of 897{{nbsp}}nM, 694{{nbsp}}nM, and 1450–3423{{nbsp}}nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA). The predicted log P of HMA is 0.6.{{cite web | title=3-O-Methyl-Alpha-Methyldopamine | work = PubChem | publisher = U.S. National Library of Medicine | url=https://pubchem.ncbi.nlm.nih.gov/compound/197139 | access-date=14 November 2024}}