{{Infobox drug | verifiedrevid = 408409035 | drug_name = | image = Cyclopropylmescaline.svg | image_class = skin-invert-image | width = 250px | caption = | image2 = Cyclopropylmescaline-3d-sticks.png | image_class2 = bg-transparent | width2 = 250px | caption2 =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonin 5-HT<sub>2</sub> receptor agonist; Serotonin 5-HT<sub>2A</sub> receptor agonist; Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = ≤20 minutes<ref name="PiHKAL" /> | elimination_half-life = | duration_of_action = 12–18 hours<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 207740-23-6 | CAS_supplemental = | PubChem = 44350143 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21106288 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = D9268U4GS8 | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 421458 | NIAID_ChemDB = | PDB_ligand = | synonyms = CPM; 4-Cyclopropylmethoxy-3,5-methoxyphenethylamine
<!-- Chemical data --> | IUPAC_name = 2-[4-(cyclopropylmethoxy)-3,5-dimethoxyphenyl]ethan-1-amine | C=14 | H=21 | N=1 | O=3 | SMILES = COc2cc(cc(OC)c2OCC1CC1)CCN | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LNTBHKZMYJTHTH-UHFFFAOYSA-N }}
'''Cyclopropylmescaline''' ('''CPM'''), also known as '''4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine''', is a psychedelic drug of the phenethylamine and scaline families related to mescaline.<ref name="PiHKAL" /> It is taken orally and has a very long duration of 12 to 18{{nbsp}}hours.<ref name="PiHKAL" />
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') and other publications, Alexander Shulgin lists CPM's dose as 60 to 80{{nbsp}}mg orally and its duration as 12 to 18{{nbsp}}hours.<ref name="PiHKAL">{{CitePiHKAL}} [https://www.erowid.org/library/books_online/pihkal/pihkal037.shtml CPM Entry in ''PiHKAL'']</ref><ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://bitnest.netfirms.com/external/Books/NIDA146.74}}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}}</ref> Its onset is within 20{{nbsp}}minutes and peak effects occurred at around 1.5{{nbsp}}hours.<ref name="PiHKAL" /> The drug is approximately 5{{nbsp}}times as potent as mescaline and is longer-lasting in comparison.<ref name="PiHKAL" /><ref name="JacobShulgin1994" /><ref name="Shulgin2003" />
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.<ref name="PiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== CPM acts as a serotonin 5-HT<sub>2</sub> receptor full agonist, including of the serotonin 5-HT<sub>2A</sub>, 5-HT<sub>2B</sub>, and 5-HT<sub>2C</sub> receptors.<ref name="WallachCaoCalkins2023">{{cite journal | vauthors = 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 | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | article-number = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 }}</ref><ref name="JainGumpperSlocum2025">{{cite journal | vauthors = 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 | title = The polypharmacology of psychedelics reveals multiple targets for potential therapeutics | journal = Neuron | volume = 113 | issue = 19 | pages = 3129–3142.e9 | date = October 2025 | pmid = 40683247 | doi = 10.1016/j.neuron.2025.06.012 | url = }}</ref>
==Chemistry== ===Synthesis=== The chemical synthesis of CPM has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of CPM include mescaline, escaline, proscaline, allylescaline, methallylescaline, and cycloproscaline, among others.<ref name="PiHKAL" /><ref name="JacobShulgin1994" />
==History== CPM was described in the scientific literature by Alexander Shulgin by 1994.<ref name="JacobShulgin1994" /> Subsequently, it was further described by Shulgin in his 1991 book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" />
==Society and culture== ===Legal status=== ====Canada==== CPM is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
== See also == * Scaline
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/37 Cyclopropylmescaline (CPM) - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal037.shtml Cyclopropylmescaline (CPM) - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/37 Cyclopropylmescaline (CPM) - PiHKAL - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Phenethylamines}}
Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2C agonists Category:Cyclopropyl compounds Category:PiHKAL Category:Psychedelic phenethylamines Category:Scalines