Chemistry:2,6-Dimethoxyamphetamine

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2,6-Dimethoxyamphetamine (2,6-DMA), also known as DMA-5, is a drug of the phenethylamine and amphetamine families.[1] It is one of the positional isomers of dimethoxyamphetamine.[1]

The drug showed very low affinity for serotonin receptors in rat stomach fundus strips (A2 = 8,130 nM).[1][2] In a subsequent study, it showed no affinity for the serotonin 5-HT2A or 5-HT2C receptors (Ki = >10,000 nM).[3] 2,6-DMA only partially substituted for DOM in rodent drug discrimination tests, with a maximum responding of 41% and behavioral disruption at higher doses.[4][5] It did not substitute for dextroamphetamine in these tests.[5][6] The drug has not been tested in humans and its effects in humans are unknown.[1]

2,6-DMA was first described in the scientific literature by Alexander Shulgin by 1969.[7] At that time, he had not yet synthesized it and did not report its effects.[7] 2,6-DMA is a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA) and hence is a Schedule I controlled substance in the United States.[1]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "#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. ↑ "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem 23 (3): 294–299. March 1980. doi:10.1021/jm00177a017. PMID 7365744. 
  3. ↑ "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. 
  4. ↑ "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. 
  5. ↑ 5.0 5.1 "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. 
  6. ↑ "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. 
  7. ↑ 7.0 7.1 "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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