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DMCPA

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DMCPA
Clinical data
Other names25D-CPA; 2,5-Dimethoxy-4-methylphenylcyclopropylamine; 4-Methyl-2,5-dimethoxyphenylcyclopropylamine
Routes of
administration		Oral[1]
Drug classSerotonin 5-HT2A receptor agonist; Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action1 hour[1]
Duration of action4–8 hours[1]
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)

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]

Use and effects

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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists DMCPA's dose as 15 to 20 mg orally and its duration as 4 to 8 hours.[1] Its onset is 1 hour.[1] The effects of DMCPA have been reported to include psychedelic visuals such as visual movement, fantasy, eroticism, feeling decoupled from one's experience and environment, feeling like the aura before a seizure, lightheadedness, feeling loss of control and uncomfortable, muscle tremors, mild anorexia, bizarre and colorful dreams during subsequent sleep, and no next-day hangover.[1] It was said to have too much in the way of physical side effects and hints of physical toxicity at the highest assessed dose.[1]

Interactions

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Pharmacology

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Pharmacodynamics

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

Chemistry

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Synthesis

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

Analogues

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Analogues of DMCPA include 3,4,5-trimethoxytranylcypromine (TMT), tranylcypromine, and DOM, among others.[1]

History

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

Society and culture

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United Kingdom

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

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 11 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 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.
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