4-Hydroxy-3-methoxyamphetamine

4-Hydroxy-3-methoxyamphetamine
Clinical data
Other names	HMA; 3-Methoxy-4-hydroxyamphetamine; 3-O-Methyl-α-methyldopamine
Drug class	Serotonin–norepinephrine–dopamine releasing agent
Identifiers
	IUPAC name 4-(2-aminopropyl)-2-methoxyphenol;
CAS Number	13026-44-3;
PubChem CID	197139;
ChemSpider	170725;
UNII	UW5V6G007J;
ChEBI	CHEBI:173516;
ChEMBL	ChEMBL1347;
Chemical and physical data
Formula	C10H15NO2
Molar mass	181.235 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC(=C(C=C1)O)OC)N;
	InChI InChI=1S/C10H15NO2/c1-7(11)5-8-3-4-9(12)10(6-8)13-2/h3-4,6-7,12H,5,11H2,1-2H3; Key:GPBOYXOSSQEJBH-UHFFFAOYSA-N;

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 EC₅₀Tooltip half-maximal effective concentration 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]

References

^ 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.
^ 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.
^ 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.
^ ^a ^b Blough B (July 2008). "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. Archived from the original on 4 November 2024. TABLE 11-2 Comparison of the DAT- and NET-Releasing Activity of a Series of Amphetamines [...]
^ ^a ^b 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.
^ "3-O-Methyl-Alpha-Methyldopamine". PubChem. U.S. National Library of Medicine. Retrieved 14 November 2024.

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[delaTorreFarréPizarro2004-1] 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.

[RietjensHondebrinkWesterink2012-2] 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.

[LuethiKolaczynskaWalter2019-3] 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.

[Blough2008-4] Blough B (July 2008). "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. Archived from the original on 4 November 2024. TABLE 11-2 Comparison of the DAT- and NET-Releasing Activity of a Series of Amphetamines [...]

[Yubero-LahozAyestasBlough2012-5] 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.

[PubChem-6] "3-O-Methyl-Alpha-Methyldopamine". PubChem. U.S. National Library of Medicine. Retrieved 14 November 2024.

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[6]

4-Hydroxy-3-methoxyamphetamine

See also

References