Cyclopropylmescaline

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Cyclopropylmescaline
Clinical data
Other namesCPM; 4-Cyclopropylmethoxy-3,5-methoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action≤20 minutes[1]
Duration of action12–18 hours[1]
Identifiers
  • 2-[4-(cyclopropylmethoxy)-3,5-dimethoxyphenyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO3
Molar mass251.326 g·mol−1
3D model (JSmol)
  • COc2cc(cc(OC)c2OCC1CC1)CCN
  • InChI=1S/C14H21NO3/c1-16-12-7-11(5-6-15)8-13(17-2)14(12)18-9-10-3-4-10/h7-8,10H,3-6,9,15H2,1-2H3 checkY
  • Key:LNTBHKZMYJTHTH-UHFFFAOYSA-N checkY
  (verify)

Cyclopropylmescaline (CPM), also known as 4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1] It is taken orally and has a very long duration of 12 to 18 hours.[1]

Use and effects

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists the dose range of CPM as 60 to 80 mg and its duration as 12 to 18 hours.[1][2][3] Its onset is within 20 minutes and peak effects occurred at around 1.5 hours.[1] The drug is approximately 5 times as potent as mescaline and is longer-lasting in comparison.[1][2][3]

The effects of CPM have been reported to include remarkable closed-eye visuals and fantasy, mental imagery synchronized with music, not much in terms of open-eye visuals, heightened tactile awareness, not much insight, daydreaming about eroticism, feeling exposed and vulnerable, sounds including voices and even music feeling intrusive and irritating, and interference with sleep and feeling tired due to its very long duration.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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CPM acts as a serotonin 5-HT2 receptor full agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[4][5]

Chemistry

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Analogues

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Analogues of CPM include mescaline, escaline, proscaline, allylescaline, methallylescaline, and cycloproscaline, among others.[1][2]

History

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CPM was described in the scientific literature by Alexander Shulgin by 1994.[2] Subsequently, it was further described by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]

See also

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References

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  1. ^ a b c d e f g h i j k Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. CPM Entry in PiHKAL
  2. ^ a b c d Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr. 146: 74–91. PMID 8742795.
  3. ^ a b Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.
  4. ^ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1) 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  5. ^ 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 (October 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics". Neuron. 113 (19): 3129–3142.e9. doi:10.1016/j.neuron.2025.06.012. PMID 40683247.
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