Chemistry:4-Hydroxy-3-methoxymethamphetamine
From HandWiki
4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA).[1][2][3] It is a slightly more potent stimulant than MDMA in rodents.[4] The drug is substantially less potent than MDMA as a monoamine releasing agent in vitro.[5][6] Nonetheless, HMMA has been found to induce the release of serotonin, norepinephrine, and dopamine with EC50 values of 589 nM, 625 nM, and 607–2884 nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][6] The predicted log P of HMMA is 1.2.[7]
See also
- 4-Hydroxy-3-methoxyamphetamine (HMA)
- 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine)
- 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine)
- 2,4,5-Trihydroxyamphetamine (THA)
- 2,4,5-Trihydroxymethamphetamine (THMA)
- 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.
- ↑ "Effects of 3,4-methylenedioxymethamphetamine (MDMA) and its main metabolites on cardiovascular function in conscious rats". British Journal of Pharmacology 171 (1): 83–91. January 2014. doi:10.1111/bph.12423. PMID 24328722.
- ↑ 5.0 5.1 "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.
- ↑ 6.0 6.1 "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.
- ↑ "4-Hydroxy-3-methoxymethamphetamine". PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/3081137.
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