4-Hydroxy-3-methoxymethamphetamine explained

Class:Serotonin–norepinephrine–dopamine releasing agent
Cas Number:117652-28-5
Pubchem:3081137
Chemspiderid:2338803
Unii:RBY3J6H4JW
Synonyms:HMMA; 4-Hydroxy-3-methoxy-N-methylamphetamine; 3-Methoxy-4-hydroxymethamphetamine; 3-Methoxy-4-hydroxy-N-methylamphetamine
Iupac Name:2-methoxy-4-[2-(methylamino)propyl]phenol
C:11
H:17
N:1
O:2
Smiles:CC(CC1=CC(=C(C=C1)O)OC)NC
Stdinchi: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
Stdinchikey: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 values of 589nM, 625nM, and 607–2884nM, respectively, and hence acts as a lower-potency serotonin–norepinephrine–dopamine releasing agent (SNDRA). The predicted log P of HMMA is 1.2.[7]

See also

Notes and References

  1. de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, Segura J, Camí J . Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition . Therapeutic Drug Monitoring . 26 . 2 . 137–144 . April 2004 . 15228154 . 10.1097/00007691-200404000-00009 .
  2. Rietjens SJ, Hondebrink L, Westerink RH, Meulenbelt J . 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 . 23030234 . 10.3109/10408444.2012.725029 .
  3. Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME . Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems . Journal of Psychopharmacology . 33 . 7 . 831–841 . July 2019 . 31038382 . 10.1177/0269881119844185 . 8269116 .
  4. Schindler CW, Thorndike EB, Blough BE, Tella SR, Goldberg SR, Baumann MH . 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 . 24328722 . 3874698 . 10.1111/bph.12423 .
  5. Book: Blough B . Dopamine-releasing agents . Dopamine Transporters: Chemistry, Biology and Pharmacology . 305–320 . July 2008 . 978-0-470-11790-3 . Wiley . Hoboken [NJ] . https://archive.org/details/dopaminetranspor0000unse/page/310/ . https://archive.today/20241104022653/https://archive.org/details/dopaminetranspor0000unse/page/310/mode/2up . 4 November 2024 . TABLE 11-2 Comparison of the DAT- and NET-Releasing Activity of a Series of Amphetamines [...].
  6. Yubero-Lahoz S, Ayestas MA, Blough BE, Partilla JS, Rothman RB, de la Torre R, Baumann MH . 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 . 22079770 . 3253888 . 10.1016/j.ejphar.2011.10.033 .
  7. Web site: 4-Hydroxy-3-methoxymethamphetamine . PubChem . U.S. National Library of Medicine . 14 November 2024.

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