Chemistry:2,3-Dimethoxyamphetamine

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2,3-Dimethoxyamphetamine (2,3-DMA), also known as DMA-2, is a drug of the phenethylamine and amphetamine families.[1][2] It is one of the positional isomers of dimethoxyamphetamine.[1]

The drug showed weak affinity for serotonin receptors in rat stomach fundus strips (A2 = 2,880 nM).[3] In a subsequent study, 2,3-DMA showed very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 4,280 nM and >10,000 nM, respectively).[4] It did not show activity as a norepinephrine releasing agent in vitro.[5] The drug is behaviorally active in mice.[2] 2,3-DMA did not substitute for DOM in rodent drug discrimination tests.[1][6] However, it did partially substitute for 5-MeO-DMT in these tests.[1][7] As with DOM, the drug did not substitute for dextroamphetamine in drug discrimination tests.[8][9] It produced behavioral disruption at higher doses.[8][9] 2,3-DMA does not appear to have been tested in humans.[1][2][6]

2,3-DMA was first described in the scientific literature by 1968.[1][5] Alexander Shulgin first described 2,3-DMA in 1969 but had not yet synthesized it and did not report its effects.[10]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "#34. 2,3-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley, CA: Transform Press. 2011. pp. 51–54. ISBN 978-0-9630096-3-0. OCLC 709667010. https://archive.org/details/shulgin-index-vol-1/page/51/mode/1up. 
  2. ↑ 2.0 2.1 2.2 "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 55–97. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. 
  3. ↑ "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem 23 (3): 294–299. March 1980. doi:10.1021/jm00177a017. PMID 7365744. 
  4. ↑ "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". J Med Chem 43 (16): 3074–3084. August 2000. doi:10.1021/jm9906062. PMID 10956215. 
  5. ↑ 5.0 5.1 "The chemorelease of norepinephrine from mouse hearts by substituted amphetamines". J Med Chem 11 (4): 896–897. July 1968. doi:10.1021/jm00310a048. PMID 5677681. 
  6. ↑ 6.0 6.1 "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav 17 (4): 603–607. October 1982. doi:10.1016/0091-3057(82)90330-6. PMID 6965276. 
  7. ↑ "Behavioral properties of psychoactive phenylisopropylamines in rats". Eur J Pharmacol 76 (4): 353–360. December 1981. doi:10.1016/0014-2999(81)90106-0. PMID 7327208. 
  8. ↑ 8.0 8.1 "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav 22 (5): 723–729. May 1985. doi:10.1016/0091-3057(85)90520-9. PMID 3839309. 
  9. ↑ 9.0 9.1 "Discriminative stimulus properties of phenylisopropylamine derivatives". Drug Alcohol Depend 17 (2–3): 119–134. June 1986. doi:10.1016/0376-8716(86)90003-7. PMID 2874967. 
  10. ↑ "Structure--activity relationships of one-ring psychotomimetics". Nature 221 (5180): 537–541. February 1969. doi:10.1038/221537a0. PMID 5789297. Bibcode: 1969Natur.221..537S. 




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