Wikipedia

DMCPA

DMCPA, also known as 2,5-dimethoxy-4-methylphenylcyclopropylamine, is a psychedelic drug of the phenethylamine, amphetamine, and phenylcyclopropylamine families related to DOM.[1] It is a derivative of tranylcypromine and is the cyclized phenethylamine analogue of DOM in which the α and β positions have been connected with a carbon atom to form a cyclopropyl group.[1]

DMCPA
Clinical data
Other names25D-CPA; 2,5-Dimethoxy-4-methylphenylcyclopropylamine
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-(2,5-dimethoxy-4-methylphenyl)cyclopropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H17NO2
Molar mass207.273 g·mol−1
3D model (JSmol)
  • O(c1c(cc(OC)c(c1)C2CC2N)C)C
  • InChI=1S/C12H17NO2/c1-7-4-12(15-3)9(6-11(7)14-2)8-5-10(8)13/h4,6,8,10H,5,13H2,1-3H3 checkY
  • Key:HYVPPECPQRBJEQ-UHFFFAOYSA-N checkY
  (verify)

Use and effects

edit

In Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved), the dose range is listed as 15 to 20 mg and the duration is listed as 4 to 8 hours.[1] DMCPA produces open-eye visuals, anorexia, and psychedelic dreams.[1] One of the reports in PiHKAL gave it a +++ on the Shulgin Rating Scale.[1]

Interactions

edit

Pharmacology

edit

Pharmacodynamics

edit

The comprehensive receptor interactions of DMCPA have been studied.[2]

Chemistry

edit

Synthesis

edit

The chemical synthesis of DMCPA has been described.[1]

History

edit

DMCPA was first described in the scientific literature by at least 1974.[3]

Society and culture

edit
edit

United Kingdom

edit

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[4]

See also

edit

References

edit
  1. 1 2 3 4 5 6 7 DMCPA Entry in PiHKAL
  2. ↑ Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, Suomivuori CM, Huang XP, Shub L, DiBerto JF, Kim K, DeLeon C, Krumm BE, Fay JF, Keiser M, Hauser AS, Dror RO, Shoichet B, Gloriam DE, Nichols DE, Roth BL (July 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics" (PDF). Neuron. doi:10.1016/j.neuron.2025.06.012. PMID 40683247.
  3. ↑ Aldous FA, Barrass BC, Brewster K, Buxton DA, Green DM, Pinder RM, Rich P, Skeels M, Tutt KJ (October 1974). "Structure-activity relationships in psychotomimetic phenylalkylamines". J Med Chem. 17 (10): 1100–1111. doi:10.1021/jm00256a016. PMID 4418757.
  4. ↑ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.
edit
Retrieved from "https://en.wikipedia.org/w/index.php?title=DMCPA&oldid=1340520783"