4-Hydroxy-3-methoxymethamphetamine

4-Hydroxy-3-methoxymethamphetamine

Clinical data
Other names	HMMA; 4-Hydroxy-3-methoxy-N-methylamphetamine; 3-Methoxy-4-hydroxymethamphetamine; 3-Methoxy-4-hydroxy-N-methylamphetamine
Drug class	Serotonin–norepinephrine–dopamine releasing agent
Identifiers
IUPAC name 2-methoxy-4-[2-(methylamino)propyl]phenol
CAS Number	117652-28-5^Y
PubChem CID	3081137
ChemSpider	2338803
UNII	RBY3J6H4JW
CompTox Dashboard (EPA)	DTXSID70922503
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC(=C(C=C1)O)OC)NC
InChI InChI=1S/C11H17NO2/c1-8(12-2)6-9-4-5-10(13)11(7-9)14-3/h4-5,7-8,12-13H,6H2,1-3H3 Key:UVDWYWYWOMOEFX-UHFFFAOYSA-N

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 EC₅₀Tooltip half-maximal effective concentration 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

1. de la Torre R, Farré 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.
2. 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.
3. 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.
4. Schindler CW, Thorndike EB, Blough BE, Tella SR, Goldberg SR, Baumann MH (January 2014). "Effects of 3,4-methylenedioxymethamphetamine (MDMA) and its main metabolites on cardiovascular function in conscious rats". British Journal of Pharmacology. 171 (1): 83–91. doi:10.1111/bph.12423. PMC 3874698. PMID 24328722.
5. 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.
6. 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.
7. "4-Hydroxy-3-methoxymethamphetamine". PubChem. U.S. National Library of Medicine. Retrieved 14 November 2024.