2,5-Dimethoxy-4-methylphenylcyclopropylamine

2,5-Dimethoxy-4-methylphenylcyclopropylamine (DMCPA) is a lesser-known psychedelic drug and a substituted amphetamine and phenylcyclopropylamine.^[1] DMCPA was first synthesized by Alexander Shulgin.^{[citation needed]}

DMCPA

Clinical data
Other names	25D-CPA; 2,5-Dimethoxy-4-methylphenylcyclopropylamine
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(2,5-dimethoxy-4-methylphenyl)cyclopropan-1-amine
CAS Number	714903-64-7 Y
PubChem CID	3017965
ChemSpider	2285590 Y
UNII	U2YC8RFK7B
ChEMBL	ChEMBL13530 Y
CompTox Dashboard (EPA)	DTXSID10990120
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1c(cc(OC)c(c1)C2CC2N)C)C
InChI 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 Y Key:HYVPPECPQRBJEQ-UHFFFAOYSA-N Y
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Use and effects

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[3]

See also

• Substituted methoxyphenethylamine
• Cyclized phenethylamine
• Phenylcyclopropylamine
• 3,4,5-Trimethoxytranylcypromine (TMT)
• Tranylcypromine