2C-P

Last updated

2C-P
2C-P2DACS.svg
2C-P-3d-sticks.png
Clinical data
Other names2C-Pr; 4-Propyl-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-propylphenethylamine; 2C-DOPR; 2C-DOPr; Selene
Routes of
administration 		Oral [1]
Drug class Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action 1–2 hours [1]
Peak: 3 hours [1]
Duration of action 10–16 hours [1]
Identifiers
  • 2-(2,5-dimethoxy-4-propylphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H21NO2
Molar mass 223.316 g·mol−1
3D model (JSmol)
Melting point 207 to 209 °C (405 to 408 °F) (hydrochloride)
Solubility in water 7–9 mg/mL (20 °C) mg/mL (20 °C)
  • COC1=C(CCN)C=C(OC)C(CCC)=C1
  • InChI=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 Yes check.svgY
  • Key:PZJOKFZGPTVNBF-UHFFFAOYSA-N Yes check.svgY
   (verify)

2C-P, also known as 4-propyl-2,5-dimethoxyphenethylamine or as Selene, is a psychedelic drug of the phenethylamine and 2C families. [1] [2] [3] It is taken orally and is among the most potent and long-lasting of the 2C psychedelics. [1] [2]

Contents

2C-P was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) in 1991. [1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-P's dose range as 6 to 10 mg orally and its duration as 10 to 16 hours. [1] A wider dosage range of 1 to 16 mg or more, with a typical dose estimate of 7 mg, has also been reported. [4] Shulgin wrote in PiHKAL that while most reports with doses of 6 to 12 mg were positive, a single report of 16 mg was described as a clear overdose and "physical disaster" that was "not to be repeated". [1] He described the drug as having a steep dose–response curve and advised careful individual dose titration. [1] 2C-P is also said to come on slowly, with an onset of 1 to 2 hours and peak effects not occurring until after 3 hours. [1] The drug is one of the most potent psychedelics of the 2C family, rivaled only by 2C-TFM. [1] [2] It is taken orally. [1]

The effects of 2C-P have been reported to include closed-eye imagery, beautiful psychedelic visuals, insights, emotional enhancement, increased appreciation of music and eroticism, feelings of energy flowing through oneself, physical discomfort, back and leg pain, next-day hangover, and an afterglow. [1]

Overdose

Unknown or unreported doses taken by teenagers at a Connecticut, United States 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. [5] It was reported that none of the overdose victims died [6] while CNN's "OutFront" blog claimed the police called it a "mass casualty event" [7] 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, United Kingdom, the first reported death from 2C-P. [8] 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. [9]

Interactions

2C drugs like 2C-P are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. [10] [11] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-P. [10] [11] [12] This may result in overdose and serious toxicity. [12] [10]

Pharmacology

Pharmacodynamics

2C-P activities
Target Affinity (Ki, nM)
5-HT1A 110
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 8.1 (Ki)
90 (EC50 Tooltip half-maximal effective concentration)
63% (Emax Tooltip maximal efficacy)
5-HT2B ND (Ki)
130 (EC50)
72% (Emax)
5-HT2C 40 (Ki)
ND (EC50)
ND (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 3,500
α1B, α1D ND
α2A 90
α2B, α2C ND
β1–β3 ND
D1 8,400
D2 2,300
D3 5,200
D4, D5 ND
H1 21,000
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
TAAR1 Tooltip Trace amine-associated receptor 1280 (Ki) (mouse)
20 (Ki) (rat)
560 (EC50) (mouse)
30 (EC50) (rat)
4,200 (EC50) (human)
91% (Emax) (mouse)
84% (Emax) (rat)
72% (Emax) (human)
SERT Tooltip Serotonin transporter19,000 (Ki)
30,000 (IC50 Tooltip half-maximal inhibitory concentration)
ND (EC50)
NET Tooltip Norepinephrine transporter18,000 (Ki)
94,000 (IC50)
ND (EC50)
DAT Tooltip Dopamine transporter40,000 (Ki)
198,000 (IC50)
ND (EC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [13] [14] [15]

2C-P acts as an agonist of the serotonin 5-HT2 receptors. [14] It also binds to the serotonin 5-HT1A receptor with about 14-fold lower affinity than for the serotonin 5-HT2A receptor. [14] The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition. [14] [16] It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1) and lower but still high affinity for the mouse TAAR1. [14]

In contrast to many other psychedelics, 2C-P, as well as 2C-C and certain 2C NBOMe analogues, has shown reinforcing effects in rodents. [17] [16] It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats. [17] [16] These findings suggest that 2C-P may have misuse potential. [17] [16] The mechanism by which these effects are produced is unknown. [16] 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. [17] [16] 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. [17] [16]

2C-P has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation. [16]

The drug only weakly inhibits the monoamine oxidases. [18]

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, [19] [ unreliable source? ] or white crystals. [1]

Properties

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 40 Pa (0.3 mmHg) (turning it "water white" in color), and it "spontaneously crystallized" upon cooling.

Analogues

Analogues of 2C-P include 2C-D, 2C-E, 2C-Bu, 2C-iP, and 2C-iBu, among others. [1] [2]

History

2C-P was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) in 1991. [1]

Society and 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.

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. [20]

China

As of October 2015 2C-P is a controlled substance in China. [21]

Denmark

In Denmark, 2C-P has been added to the list of Schedule B controlled substances. [22]

Finland

Scheduled in "government decree on psychoactive substances banned from the consumer market". [23]

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. [24]

United Kingdom

2C-P is a Class A drug in the UK. [25]

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). [26] The law came into effect on January 4, 2013. [27]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 "Erowid Online Books : "PIHKAL" - #36 2C-P". erowid.org. Archived from the original on 2015-04-21. Retrieved 2015-04-06.
  2. 1 2 3 4 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  3. ↑ Ger A, Ger D. "Triple Goddess of the Night". British Neuroscience Association Bulletin. 63: 28–30.
  4. ↑ Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". The International Journal of Neuropsychopharmacology. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC   6165951 . PMID   29850881.
  5. ↑ "Four overdose at Quassy Amusement Park concert - WTNH.com Connecticut". 27 November 2013. Archived from the original on 27 November 2013.
  6. ↑ "New 'it' drug? Molly's powerful, deadly cousin". HLN TV. Archived from the original on 2016-03-05. Retrieved 2015-04-06.
  7. ↑ "Police: "2C-P" and "Molly" involved in drug overdoses amusement park concert". cnn.com. Archived from the original on 2016-03-04. Retrieved 2015-04-06.
  8. ↑ Siddique H (5 February 2019). "Party drugs killed TV actor's daughter at music festival, court hears". The Guardian. Archived from the original on 5 February 2019. Retrieved 5 February 2019.
  9. ↑ "Bestival death: Ceon Broughton jailed for manslaughter". BBC News. March 1, 2019. Archived from the original on September 14, 2019. Retrieved September 3, 2019.
  10. 1 2 3 Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". Journal of Medical Toxicology. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC   3657019 . PMID   23494844.
  11. 1 2 Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochemical Pharmacology. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID   17067556.
  12. 1 2 Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  13. ↑ "Kᵢ Database". PDSP. 1 April 2025. Retrieved 1 April 2025.
  14. 1 2 3 4 5 Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  15. ↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601. Archived from the original (PDF) on 2025-05-09.
  16. 1 2 3 4 5 6 7 8 Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, et al. (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Archives of Toxicology. 95 (4): 1413–1429. Bibcode:2021ArTox..95.1413K. doi:10.1007/s00204-021-02980-x. PMID   33515270.
  17. 1 2 3 4 5 Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicology Reports. 14 101890. Bibcode:2025ToxR...1401890G. doi:10.1016/j.toxrep.2025.101890. PMC   11762925 . PMID   39867514.
  18. ↑ Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Testing and Analysis. 11 (2): 318–324. doi:10.1002/dta.2494. PMID   30188017.
  19. ↑ "Erowid 2C-P Vault : Images". erowid.org. Archived from the original on 2015-04-12. Retrieved 2015-04-06.
  20. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". The Government of Canada. April 15, 2016. Archived from the original on 2016-08-31. Retrieved 2017-06-22.
  21. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  22. ↑ "Bekendtgørelse om euforiserende stoffer - retsinformation.dk". Archived from the original on 2013-10-04. Retrieved 2013-09-13.
  23. ↑ "1130/2014".
  24. ↑ "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." (PDF). Archived from the original (PDF) on 2017-10-30. Retrieved 2017-04-21.
  25. ↑ "Bestival death: Ceon Broughton jailed for manslaughter". BBC News. BBC. 1 March 2019. Archived from the original on 1 March 2019. Retrieved 1 March 2019.
  26. ↑ "Text of S. 3190 (112th): Synthetic Drug Abuse Prevention Act of 2012 (Introduced version) - GovTrack.us". GovTrack.us. Archived from the original on 2015-04-12. Retrieved 2015-04-06.
  27. ↑ "Rules - 2013 > Establishment of Drug Codes for 26 Substances". Archived from the original on 2015-03-22. Retrieved 2015-04-06.
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