Chemistry:4-Hydroxy-3-methoxyamphetamine
From HandWiki
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 EC50 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
- Substituted amphetamine
- 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)
References
- ↑ "Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition". Therapeutic Drug Monitoring 26 (2): 137–144. April 2004. doi:10.1097/00007691-200404000-00009. PMID 15228154.
- ↑ "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. doi:10.3109/10408444.2012.725029. PMID 23030234.
- ↑ "Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems". Journal of Psychopharmacology 33 (7): 831–841. July 2019. doi:10.1177/0269881119844185. PMID 31038382.
- ↑ 4.0 4.1 "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. July 2008. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf.
- ↑ 5.0 5.1 "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. doi:10.1016/j.ejphar.2011.10.033. PMID 22079770.
- ↑ "3-O-Methyl-Alpha-Methyldopamine". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/197139.
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