3,4-Dimethoxyamphetamine

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3,4-Dimethoxyamphetamine
3,4-Dimethoxyamphetamine.svg
Clinical data
Other names3,4-DMA; Dimethoxyamphetamine; DMA; 3,4-Dimethoxy-α-methylphenethylamine; α-Methylhomoveratrylamine; EA-1316; NSC-144717
Drug class Serotonergic psychedelic; Hallucinogen
Identifiers
  • 1-(3,4-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.985 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H17NO2
Molar mass 195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3
  • Key:KAZPHAGSWZTKDW-UHFFFAOYSA-N

3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. [1] [2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers. [1] [2]

The drug has been assessed in various biochemical and preclinical studies. [2] It has been tried in humans at doses of up to 700 mg intravenously, with mescaline-like effects reported. [2] [1] 3,4-DMA is also orally active and has produced sympathomimetic effects at a dose of 160 mg. [2] [1] Its duration of action is unknown. [2] [1]

Its affinity (Ki) for the rat serotonin 5-HT2A receptor has been assessed [2] and was found to be 43,300 nM. [3] For comparison, the affinity of para-methoxyamphetamine (PMA) was 33,600 nM, of 2,5-dimethoxyamphetamine (2,5-DMA) was 5,200 nM, and of 2,5-dimethoxy-4-methylamphetamine (DOM) was 100 nM in the same study. [3] 3,4-DMA has been found to be a monoamine oxidase inhibitor (MAOI), with an IC50 Tooltip half-maximal inhibitory concentration of 20,000 nM for monoamine oxidase A (MAO-A), whereas it was inactive at monoamine oxidase B (MAO-B) (IC50 > 100,000 nM). [4] [5]

3,4-DMA produces 3-methoxy-4-hydroxyamphetamine (MHA) as its major metabolite in dogs and monkeys. [2]

See also

References

  1. 1 2 3 4 5 Shulgin AT, Shulgin A (1991). "#55 3,4-DMA; 3,4-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN   9780963009609. OCLC   25627628.
  2. 1 2 3 4 5 6 7 8 Shulgin A, Manning T, Daley PF (2011). "#38. DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN   978-0-9630096-3-0.
  3. 1 2 Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID   6479216.
  4. ↑ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi: 10.3389/fphar.2019.01590 . PMC   6989591 . PMID   32038257.
  5. ↑ Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". J Med Chem. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID   15801832.
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