Article · Wikipedia archive · Last revised Jul 9, 2026

4-Hydroxy-3-methoxymethamphetamine

4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasing agent in vitro. 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). The predicted log P of HMMA is 1.2.

Last revised
Jul 9, 2026
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HMMA
Clinical data
Other namesHMMA; 4-Hydroxy-3-methoxy-N-methylamphetamine; 3-Methoxy-4-hydroxymethamphetamine; 3-Methoxy-4-hydroxy-N-methylamphetamine
Drug classSerotonin–norepinephrine–dopamine releasing agent
Identifiers
  • 2-methoxy-4-[2-(methylamino)propyl]phenol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1)O)OC)NC
  • 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).123 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.56 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).56 The predicted log P of HMMA is 1.2.7

See also

See also

References

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.