2C-P

Clinical data
Other names	2C-Pr; 4-Propyl-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-propylphenethylamine; 2C-DOPR; 2C-DOPr; Selene
Routes of administration	Oral[1]
Drug class	Serotonin5-HT2 receptoragonist;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
IUPAC name 2-(2,5-dimethoxy-4-propylphenyl)ethan-1-amine
CAS Number	207740-22-5 Y
PubChemCID	44350080
ChemSpider	21106226 Y
UNII	DPS1JI878J
ChEMBL	ChEMBL339136 Y
CompTox Dashboard(EPA)	DTXSID30174849
Chemical and physical data
Formula	C13H21NO2
Molar mass	223.316 g·mol−1
3D model (JSmol)	Interactive image
Melting point	207 to 209 °C (405 to 408 °F) (hydrochloride)
Solubility in water	7–9 mg/mL (20 °C) mg/mL (20 °C)
SMILES COC1=C(CCN)C=C(OC)C(CCC)=C1
InChI 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 Y Key:PZJOKFZGPTVNBF-UHFFFAOYSA-N Y
(verify)

2C-P, also known as4-propyl-2,5-dimethoxyphenethylamine or asSelene, is apsychedelic drug of thephenethylamine and2C families.^[1][2][3] It is takenorally and is among the mostpotent and long-lasting of the 2C psychedelics.^[1][2]

2C-P was first described in the literature byAlexander Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved) in 1991.^[1]

In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists 2C-P's dose range as 6 to 10 mgorally and itsduration 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 inPiHKAL that while most reports with doses of 6 to 12 mg were positive, a single report of 16 mg was described as a clearoverdose and "physical disaster" that was "not to be repeated".^[1] He described the drug as having a steepdose–response curve and advised careful individual dose titration.^[1] 2C-P is also said to come on slowly, with anonset of 1 to 2 hours and peak effects not occurring until after 3 hours.^[1] The drug is one of the mostpotentpsychedelics of the2C family, rivaled only by2C-TFM.^[1][2] It is takenorally.^[1]

The effects of 2C-P have been reported to includeclosed-eyeimagery, beautifulpsychedelic visuals,insights,emotional enhancement, increased appreciation ofmusic anderoticism, feelings ofenergy flowing through oneself,physical discomfort,back andleg pain, next-dayhangover, and anafterglow.^[1]

Unknown or unreported doses taken by teenagers at aConnecticut,United States concert in September 2013 caused seven people to require emergency medical help includingCPR anddefibrillation 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] whileCNN'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 forMDMA.

Louella Fletcher-Michie, the daughter of actorJohn Michie, died from a 2C-P overdose in September 2017 at theBestival festival inDorset,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]

2C drugs like 2C-P are known to bemetabolized by themonoamine oxidase (MAO)enzymesMAO-A andMAO-B.^[10][11]Monoamine oxidase inhibitors (MAOIs) such asphenelzine,tranylcypromine,moclobemide, andselegiline may potentiate the effects of 2C drugs like 2C-P.^[10][11][12] This may result inoverdose and serioustoxicity.^[12][10]

2C-P acts as anagonist of theserotonin5-HT₂ receptors.^[14] It also binds to the serotonin5-HT_1A receptor with about 14-fold loweraffinity than for the serotonin5-HT_2A receptor.^[14] The drug shows little or no affinity for themonoamine transporters (MATs) and shows very weak or negligiblemonoamine reuptake inhibition.^[14][16] It shows high affinity for the rattrace 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 as2C-C and certain 2CNBOMeanalogues, has shownreinforcing effects in rodents.^[17][16] It producesdose-dependentconditioned place preference (CPP) in mice andself-administration in rats.^[17][16] These findings suggest that 2C-P may havemisuse potential.^[17][16] Themechanism by which these effects are produced is unknown.^[16] However, 2C-P was found to decreasedopamine transporter (DAT)expression and to increase DATphosphorylation in thenucleus accumbens similarly tomethamphetamine in rodents.^[17][16] Decreased DAT expression may result in reduceddopaminereuptake, while DAT phosphorylation is associated with dopaminereverse transport andefflux, in turn increasingextracellular dopamine levels.^[17][16]

2C-P has also been found to produceneurotoxicity at high doses in rodents, which appears to be mediated vianeuroinflammation.^[16]

The drug only weakly inhibits themonoamine oxidases.^[18]

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]

Alexander Shulgin's 2C-P crude freebase (soluble in chloroform), after "removal of the solvent under vacuum," was anoff-white colored oil which hedistilled at 100–110 °C at 40 Pa (0.3 mmHg) (turning it "water white" in color), and it "spontaneously crystallized" upon cooling.

Analogues of 2C-P include2C-D,2C-E,2C-Bu,2C-iP, and2C-iBu, among others.^[1][2]

2C-P was first described in the literature byAlexander Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved) in 1991.^[1]

In the first episode of theCBS fictional TV drama seriesBattle Creek, a local police detective is tasked with solving a double murder where an assisting FBI agent claims the victims were operating aclandestine laboratory manufacturing 2C-P.

2C-P is not scheduled by theUnited Nations'Convention on Psychotropic Substances.

As of October 31, 2016; 2C-P is a controlled substance (Schedule III) in Canada.^[20]

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

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

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

2C-P is anAnlage I controlled drug.

TheRiksdag added 2C-P toNarcotic Drugs Punishments Act underswedish schedule I ("substances, plant materials and fungi which normally do not have medical use" ) as of August 16, 2016, published byMedical Products Agency (MPA) in regulationHSLF-FS 2016:80 listed as 2,5-dimetoxi-4-propylfenetylamin.^[24]

2C-P is aClass A drug in the UK.^[25]

2C-P was placed intoSchedule I (with the DEA Drug Code of 7524) making it illegal to possess, distribute and/or manufacture without a license in theUnited States by an act of theUS Congress on July 9, 2012 when US PresidentBarack Obama signed theSynthetic Drug Abuse Prevention Act of 2012 (SDAPA).^[26] The law came into effect on January 4, 2013.^[27]

• 2C (psychedelics)

• 2C-P - Isomer Design
• 2C-P - PsychonautWiki
• 2C-P - Erowid
• 2C-P - PiHKAL - Erowid
• 2C-P - PiHKAL - Isomer Design
• 2C-P: The Strongest Member of the 2C Family of Psychedelics - Tripsitter

• Drugs not assigned an ATC code
• 5-HT2A agonists
• 5-HT2B agonists
• 2C (psychedelics)
• Designer drugs
• PiHKAL
• Propyl compounds
• Psychedelic phenethylamines
• Serotonin receptor agonists
• TAAR1 modulators

• CS1 German-language sources (de)
• CS1 Chinese-language sources (zh)
• Articles with short description
• Short description is different from Wikidata
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Drugs with no legal status
• All articles lacking reliable references
• Articles lacking reliable references from October 2017