2C-P
{{Infobox drug
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| verifiedrevid = 477216468
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| image = 2C-P2DACS.svg
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| image2 = 2C-P-3d-sticks.png
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| routes_of_administration = Oral
| class = Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
| ATC_prefix = None
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| duration_of_action = 10–16 hours
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 207740-22-5
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| PubChem = 44350080
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106226
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| UNII = DPS1JI878J
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| ChEMBL = 339136
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| synonyms = 2C-Pr; 2,5-Dimethoxy-4-propylphenethylamine; 4-Propyl-2,5-dimethoxyphenethylamine
| IUPAC_name = 2-(2,5-dimethoxy-4-propylphenyl)ethan-1-amine
| C=13 | H=21 | N=1 | O=2
| SMILES = COC1=C(CCN)C=C(OC)C(CCC)=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H21NO2/c1-4-5-10-8-13(16-3)11(6-7-14)9-12(10)15-2/h8-9H,4-7,14H2,1-3H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PZJOKFZGPTVNBF-UHFFFAOYSA-N
| solubility = 7{{ndash}}9{{nbsp}}mg/mL (20{{nbsp}}°C)
| melting_point = 207
| melting_high = 209
| melting_notes = (hydrochloride)
}}
2C-P, also known as 2,5-dimethoxy-4-propylphenethylamine, is a relatively potent and long-acting psychedelic phenethylamine of the 2C family.
Dosage
In his book PiHKAL, Shulgin listed 2C-P's dosage range as 6–10 mg and wrote that while most reports with dosages between 6 and 12 mg were favorable, "there was one report of an experience in which a single dosage of 16 mg was clearly an overdose, with the entire experiment labeled a physical disaster, not to be repeated." He cautioned readers regarding dosing with 2C-P by commenting that "a consistent observation is that there may not be too much latitude in dosage between that which would be modest, or adequate, and that which would be excessive. The need for individual titration would be most important with this compound." 2C-P is one of the most potent compounds in the 2C family of psychedelics, rivaled only by 2C-TFM. A wider dosage range of 1 to 16{{nbsp}}mg or more, with a dose estimate of 7{{nbsp}}mg, has also been reported.{{cite journal | vauthors = Luethi D, Liechti ME | title = Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics | journal = Int J Neuropsychopharmacol | volume = 21 | issue = 10 | pages = 926–931 | date = October 2018 | pmid = 29850881 | pmc = 6165951 | doi = 10.1093/ijnp/pyy047 | url = }}
Effects
2C-P produces intense hallucinogenic, psychedelic, and entheogenic effects including open eye visualizations and closed-eye visualizations. It can have a very slow onset if ingested, and peak effects reportedly do not occur for 3 to 5 hours. The peak lasts for five to ten hours, with the overall experience lasting up to 20 hours.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C drugs like 2C-P are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-P.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This may result in overdose and serious toxicity.
Overdoses and deaths
Unknown (or unreported) dosages taken by teenagers at a Connecticut, US concert in September 2013 caused seven people to require emergency medical help including CPR and defibrillation to resuscitate some of them, with all seven being taken to a hospital and four of those being hospitalized until at least the next day.{{cite web|url=http://www.wtnh.com/news/connecticut/four-overdose-at-quassy-amusement-park-concert|archive-url=https://web.archive.org/web/20131127001211/http://www.wtnh.com/news/connecticut/four-overdose-at-quassy-amusement-park-concert|url-status=dead|archive-date=27 November 2013|title=Four overdose at Quassy Amusement Park concert - WTNH.com Connecticut|date=27 November 2013}} It was reported that none of the overdose victims died{{cite news | url = http://www.hlntv.com/video/2013/09/23/2c-p-drug-hallucinate-overdose-concert-party | title = New 'it' drug? Molly's powerful, deadly cousin | publisher = HLN TV | access-date = 2015-04-06 | archive-date = 2016-03-05 | archive-url = https://web.archive.org/web/20160305021254/http://www.hlntv.com/video/2013/09/23/2c-p-drug-hallucinate-overdose-concert-party | url-status = live }} while CNN's "OutFront" blog claimed the police called it a "mass casualty event"{{cite web|url=http://outfront.blogs.cnn.com/2013/09/23/police-2c-p-and-molly-involved-in-drug-overdoses-amusement-park-concert/|title=Police: "2C-P" and "Molly" involved in drug overdoses amusement park concert|website=cnn.com|access-date=2015-04-06|archive-date=2016-03-04|archive-url=https://web.archive.org/web/20160304235148/http://outfront.blogs.cnn.com/2013/09/23/police-2c-p-and-molly-involved-in-drug-overdoses-amusement-park-concert/|url-status=dead}} blaming the problems on 2C-P and drugs apparently being sold as "Molly", a common name for MDMA.
Louella Fletcher-Michie, the daughter of actor John Michie, died from a 2C-P overdose in September 2017 at the Bestival festival in Dorset, UK, the first reported death from 2C-P.{{cite news |last1=Siddique |first1=Haroon |title=Party drugs killed TV actor's daughter at music festival, court hears |url=https://www.theguardian.com/uk-news/2019/feb/05/louella-fletcher-michie-death-bestival-overdose-trial |access-date=5 February 2019 |work=The Guardian |date=5 February 2019 |archive-date=5 February 2019 |archive-url=https://web.archive.org/web/20190205145432/https://www.theguardian.com/uk-news/2019/feb/05/louella-fletcher-michie-death-bestival-overdose-trial |url-status=live }} Her boyfriend was found guilty of manslaughter, for giving her the drug and failing to act to help her for over six hours after she overdosed. His conviction for failing to act was quashed in August 2020.{{Cite news | url = https://www.bbc.com/news/uk-england-dorset-47413161 | title = Bestival death: Ceon Broughton jailed for manslaughter | date = March 1, 2019 | work = BBC News | access-date = September 3, 2019 | archive-date = September 14, 2019 | archive-url = https://web.archive.org/web/20190914091148/https://www.bbc.com/news/uk-england-dorset-47413161 | url-status = live }}
Pharmacology
2C-P acts as an agonist of the serotonin 5-HT2 receptors.{{cite journal | vauthors = Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME | title = Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs) | journal = Neuropharmacology | volume = 99 | issue = | pages = 546–553 | date = December 2015 | pmid = 26318099 | doi = 10.1016/j.neuropharm.2015.08.034 | url = https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf }} It also binds to the serotonin 5-HT1A receptor with about 14-fold lower affinity than for the serotonin 5-HT2A receptor. The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition. It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1) and lower but still high affinity for the mouse TAAR1.
In contrast to many other psychedelics, 2C-P, as well as 2C-C and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.{{cite journal | vauthors = Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R | title = Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential? | journal = Toxicol Rep | volume = 14 | issue = | pages = 101890 | date = June 2025 | pmid = 39867514 | doi = 10.1016/j.toxrep.2025.101890 | url = | pmc = 11762925 | bibcode = 2025ToxR...1401890G }}{{cite journal | vauthors = Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG | title = New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents | journal = Arch Toxicol | volume = 95 | issue = 4 | pages = 1413–1429 | date = April 2021 | pmid = 33515270 | doi = 10.1007/s00204-021-02980-x | bibcode = 2021ArTox..95.1413K | url = }} It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats. These findings suggest that 2C-P may have misuse potential. The mechanism by which these effects are produced is unknown. However, 2C-P was found to decrease dopamine transporter (DAT) expression and to increase DAT phosphorylation in the nucleus accumbens similarly to methamphetamine in rodents. Decreased DAT expression may result in reduced dopamine reuptake, while DAT phosphorylation is associated with dopamine reverse transport and efflux, in turn increasing extracellular dopamine levels.
2C-P has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.
The drug only weakly inhibits the monoamine oxidases.{{cite journal | vauthors = Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR | title = Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases | journal = Drug Test Anal | volume = 11 | issue = 2 | pages = 318–324 | date = February 2019 | pmid = 30188017 | doi = 10.1002/dta.2494 | url = }}
Chemistry
2C-P is 2,5-dimethoxy-4-n-propylphenethylamine. The full name of the chemical is 2-(2,5-dimethoxy-4-propylphenyl)ethanamine. The hydrochloride salt is the most common form, normally found as a white powder,{{cite web|url=https://www.erowid.org/chemicals/2cp/2cp_images.shtml|title=Erowid 2C-P Vault : Images|website=erowid.org|access-date=2015-04-06|archive-date=2015-04-12|archive-url=https://web.archive.org/web/20150412182137/https://www.erowid.org/chemicals/2cp/2cp_images.shtml|url-status=live}}{{unreliable source?|date=October 2017}} or white crystals.{{cite web|url=https://www.erowid.org/library/books_online/pihkal/pihkal036.shtml|title=Erowid Online Books : "PIHKAL" - #36 2C-P|website=erowid.org|access-date=2015-04-06|archive-date=2015-04-21|archive-url=https://web.archive.org/web/20150421231415/https://erowid.org/library/books_online/pihkal/pihkal036.shtml|url-status=live}}
Alexander Shulgin's 2C-P crude freebase (soluble in chloroform), after "removal of the solvent under vacuum," was an off-white colored oil which he distilled at 100–110 °C at {{convert|0.3|mmHg|Pa|order=flip|abbr=on}} (turning it "water white" in color), and it "spontaneously crystallized" upon cooling.
Society and culture
=Legal status=
2C-P is not scheduled by the United Nations' Convention on Psychotropic Substances.
==Canada==
As of October 31, 2016; 2C-P is a controlled substance (Schedule III) in Canada.{{cite web | url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php | title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) | publisher=The Government of Canada | date=April 15, 2016 | language=en | access-date=2017-06-22 | archive-date=2016-08-31 | archive-url=https://web.archive.org/web/20160831014117/http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php | url-status=live }}
==China==
As of October 2015 2C-P is a controlled substance in China.{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}
==Denmark==
In Denmark, 2C-P has been added to the list of Schedule B controlled substances.{{Cite web |url=https://www.retsinformation.dk/Forms/R0710.aspx?id=137169 |title=Bekendtgørelse om euforiserende stoffer - retsinformation.dk |access-date=2013-09-13 |archive-date=2013-10-04 |archive-url=https://web.archive.org/web/20131004215445/https://www.retsinformation.dk/Forms/R0710.aspx?id=137169 |url-status=live }}
==Finland==
Scheduled in "government decree on psychoactive substances banned from the consumer market".{{cite web | url=https://finlex.fi/fi/lainsaadanto/2014/1130 | title=1130/2014 }}
==Germany==
2C-P is an Anlage I controlled drug.
==Sweden==
The Riksdag added 2C-P to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use" ) as of August 16, 2016, published by Medical Products Agency (MPA) in regulation HSLF-FS 2016:80 listed as 2,5-dimetoxi-4-propylfenetylamin.{{Cite web |url=https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLF-FS_2016_80.pdf |title=Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m. |access-date=2017-04-21 |archive-date=2017-10-30 |archive-url=https://web.archive.org/web/20171030214658/https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLF-FS_2016_80.pdf |url-status=dead }}
==United Kingdom==
2C-P is a Class A drug in the UK.{{cite news|url=https://www.bbc.co.uk/news/uk-england-dorset-47413161|title=Bestival death: Ceon Broughton jailed for manslaughter|publisher=BBC|website=BBC News|date=1 March 2019|access-date=1 March 2019|archive-date=1 March 2019|archive-url=https://web.archive.org/web/20190301102518/https://www.bbc.co.uk/news/uk-england-dorset-47413161|url-status=live}}
==United States==
2C-P was placed into Schedule I (with the DEA Drug Code of 7524) making it illegal to possess, distribute and/or manufacture without a license in the United States by an act of the US Congress on July 9, 2012 when US President Barack Obama signed the Synthetic Drug Abuse Prevention Act of 2012 (SDAPA).{{cite web|url=https://www.govtrack.us/congress/bills/112/s3190/text|title=Text of S. 3190 (112th): Synthetic Drug Abuse Prevention Act of 2012 (Introduced version) - GovTrack.us|website=GovTrack.us|access-date=2015-04-06|archive-date=2015-04-12|archive-url=https://web.archive.org/web/20150412151654/https://www.govtrack.us/congress/bills/112/s3190/text|url-status=live}} The law came into effect on January 4, 2013.{{Cite web |url=http://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr0104.htm |title=Rules - 2013 > Establishment of Drug Codes for 26 Substances |access-date=2015-04-06 |archive-date=2015-03-22 |archive-url=https://web.archive.org/web/20150322225248/http://www.deadiversion.usdoj.gov/fed_regs/rules/2013/fr0104.htm |url-status=live }}
=Popular culture=
In the first episode of the CBS fictional TV drama series Battle Creek, a local police detective is tasked with solving a double murder where an assisting FBI agent claims the victims were operating a clandestine laboratory manufacturing 2C-P.
See also
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/36 2C-P - Isomer Design]
- [https://psychonautwiki.org/wiki/2C-P 2C-P - PsychonautWiki]
- [https://www.erowid.org/chemicals/2cp/ 2C-P - Erowid]
- [https://erowid.org/library/books_online/pihkal/pihkal036.shtml 2C-P - PiHKAL - Erowid]
- [https://isomerdesign.com/pihkal/read/pk/36 2C-P - PiHKAL - Isomer Design]
- [https://tripsitter.com/2cp/ 2C-P: The Strongest Member of the 2C Family of Psychedelics - Tripsitter]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}
Category:Psychedelic phenethylamines