4-Hydroxy-3-methoxyamphetamine
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MDMA metabolite
Pharmaceutical compound
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| Other names | HMA; 3-Methoxy-4-hydroxyamphetamine; MHA; 3-O-Methyl-a-methyldopamine |
| Drug class | Serotonin-norepinephrine-dopamine releasing agent |
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| Formula | C10H15NO2 |
| Molar mass | 181.235 g*mol-1 |
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4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-O-methyl-a-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]
See also
[edit]- Substituted amphetamine
- 4-Hydroxy-3-methoxymethamphetamine (HMMA)
- 3,4-Dihydroxyamphetamine (HHA; a-methyldopamine)
- 3,4-Dihydroxymethamphetamine (HHMA; a-methylepinine)
- 2,4,5-Trihydroxyamphetamine (THA)
- 2,4,5-Trihydroxymethamphetamine (THMA)
- 3,4-Dimethoxyamphetamine (DMA)
- 3,4-Dihydroxymethcathinone (HHMC)
- 4-Hydroxy-3-methoxymethcathinone (HMMC)
References
[edit]- ^ de la Torre R, Farre M, Roset PN, Pizarro N, Abanades S, Segura M, et al. (April 2004). "Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition". Therapeutic Drug Monitoring. 26 (2): 137-144. doi:10.1097/00007691-200404000-00009. PMID 15228154.
- ^ Rietjens SJ, Hondebrink L, Westerink RH, Meulenbelt J (November 2012). "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. doi:10.3109/10408444.2012.725029. PMID 23030234.
- ^ Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, et al. (July 2019). "Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems". Journal of Psychopharmacology. 33 (7): 831-841. doi:10.1177/0269881119844185. PMC 8269116. PMID 31038382.
- ^ a b Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305-320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
- ^ a b Yubero-Lahoz S, Ayestas MA, Blough BE, Partilla JS, Rothman RB, de la Torre R, et al. (January 2012). "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. doi:10.1016/j.ejphar.2011.10.033. PMC 3253888. PMID 22079770.
- ^ "3-O-Methyl-Alpha-Methyldopamine". PubChem. U.S. National Library of Medicine. Retrieved 14 November 2024.
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