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2,3-Dimethoxyamphetamine

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2,3-Dimethoxyamphetamine
Clinical data
Other names2,3-DMA; DMA-2; NSC-172189
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1-(2,3-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C(=CC=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3
  • Key:DHLWJXGSZDJWKK-UHFFFAOYSA-N

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

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References

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  1. ^ a b c d e f Shulgin A, Manning T, Daley PF (2011). "#34. 2,3-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 51–54. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. ^ a b c Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
  3. ^ Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  4. ^ Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". J Med Chem. 43 (16): 3074–3084. doi:10.1021/jm9906062. PMID 10956215.
  5. ^ a b Benington F, Morin RD (July 1968). "The chemorelease of norepinephrine from mouse hearts by substituted amphetamines". J Med Chem. 11 (4): 896–897. doi:10.1021/jm00310a048. PMID 5677681.
  6. ^ a b Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
  7. ^ Glennon RA, Rosecrans JA, Young R (December 1981). "Behavioral properties of psychoactive phenylisopropylamines in rats". Eur J Pharmacol. 76 (4): 353–360. doi:10.1016/0014-2999(81)90106-0. PMID 7327208.
  8. ^ a b Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.
  9. ^ a b Glennon RA (June 1986). "Discriminative stimulus properties of phenylisopropylamine derivatives". Drug Alcohol Depend. 17 (2–3): 119–134. doi:10.1016/0376-8716(86)90003-7. PMID 2874967.
  10. ^ Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297.
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