2C-P, also known as 2,5-dimethoxy-4-propylphenethylamine, is a relatively
potent and long-acting
psychedelic phenethylamine
Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...
of the
2C family.
Dosage
In his book ''
PiHKAL
''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...
'', 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 16mg or more, with a dose estimate of 7mg, has also been reported.
Effects
2C-P produces intense
hallucinogenic,
psychedelic, and
entheogen
Entheogens are psychoactive substances used in spiritual and religious contexts to induce altered states of consciousness. Hallucinogens such as the psilocybin found in so-called "magic" mushrooms have been used in sacred contexts since ancie ...
ic 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
2C drugs like 2C-P are known to be
metabolized by the
monoamine oxidase
Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...
(MAO)
enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s
MAO-A
Monoamine oxidase A, also known as MAO-A, is an enzyme ( E.C. 1.4.3.4) that in humans is encoded by the ''MAOA'' gene. This gene is one of two neighboring gene family members that encode mitochondrial enzymes which catalyze the oxidative deamin ...
and
MAO-B
Monoamine oxidase B (MAO-B) is an enzyme that in humans is encoded by the ''MAOB'' gene.
The protein encoded by this gene belongs to the flavin monoamine oxidase family. It is an enzyme located in the outer mitochondrial membrane. It catalyze ...
.
Monoamine oxidase inhibitor
Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...
s (MAOIs) such as
phenelzine
Phenelzine, sold under the brand name Nardil among others, is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine family which is primarily used as an antidepressant and anxiolytic to treat depression and a ...
,
tranylcypromine
Tranylcypromine, sold under the brand name Parnate among others, is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used a ...
,
moclobemide
Moclobemide, sold under the brand names Amira, Aurorix, Clobemix, Depnil and Manerix among others, is a reversible inhibitor of monoamine oxidase A (RIMA) drug primarily used to treat Clinical depression, depression and social anxiety. It is not ...
, and
selegiline
Selegiline, also known as L-deprenyl and sold under the brand names Eldepryl, Zelapar, and Emsam among others, is a medication which is used in the treatment of Parkinson's disease and major depressive disorder. It has also been studied and us ...
may potentiate the effects of 2C drugs like 2C-P.
This may result in
overdose
A drug overdose (overdose or OD) is the ingestion or application of a drug or other substance in quantities much greater than are recommended. Retrieved on September 20, 2014. and serious
toxicity
Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...
.
Overdoses and deaths
Unknown (or unreported) dosages taken by teenagers at a
Connecticut
Connecticut ( ) is a U.S. state, state in the New England region of the Northeastern United States. It borders Rhode Island to the east, Massachusetts to the north, New York (state), New York to the west, and Long Island Sound to the south. ...
, US concert in September 2013 caused seven people to require emergency medical help including
CPR and
defibrillation
Defibrillation is a treatment for life-threatening cardiac arrhythmias, specifically ventricular fibrillation (V-Fib) and non-perfusing ventricular tachycardia (V-Tach). Defibrillation delivers a dose of electric current (often called a ''count ...
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.
It was reported that none of the overdose victims died
while
CNN
Cable News Network (CNN) is a multinational news organization operating, most notably, a website and a TV channel headquartered in Atlanta. Founded in 1980 by American media proprietor Ted Turner and Reese Schonfeld as a 24-hour cable ne ...
's "OutFront" blog claimed the police called it a "mass casualty event"
blaming the problems on 2C-P and drugs apparently being sold as "Molly", a common name for
MDMA
3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...
.
Louella Fletcher-Michie, the daughter of actor
John Michie, died from a 2C-P overdose in September 2017 at the
Bestival festival in
Dorset
Dorset ( ; Archaism, archaically: Dorsetshire , ) is a Ceremonial counties of England, ceremonial county in South West England. It is bordered by Somerset to the north-west, Wiltshire to the north and the north-east, Hampshire to the east, t ...
, UK, the first reported death from 2C-P. 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.
Pharmacology
2C-P acts as an
agonist
An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...
of the
serotonin
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
5-HT2 receptors.
It also binds to the serotonin
5-HT1A receptor with about 14-fold lower
affinity
Affinity may refer to:
Commerce, finance and law
* Affinity (law), kinship by marriage
* Affinity analysis, a market research and business management technique
* Affinity Credit Union, a Saskatchewan-based credit union
* Affinity Equity Pa ...
than for the serotonin
5-HT2A receptor.
The drug shows little or no affinity for the
monoamine transporter
Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...
s (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
2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', Shulgin lists the dosage range as 20–40 mg. 2C- ...
and certain 2C
NBOMe
The 25-NB (25''x''-NB''x'') series, or NBOMe series, also known as the ''N''-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C (psychedelics), 2C family. The most c ...
analogues, has shown
reinforcing effects in rodents.
It produces
dose-dependent conditioned place preference (CPP) in mice and
self-administration
Self-administration is, in its Medicine, medical sense, the process of a subject administering a Pharmacology, pharmacological substance to themself. A clinical example of this is the subcutaneous "self-injection" of insulin by a Diabetes, diabetic ...
in rats.
These findings suggest that 2C-P may have
misuse potential.
The
mechanism
Mechanism may refer to:
*Mechanism (economics), a set of rules for a game designed to achieve a certain outcome
**Mechanism design, the study of such mechanisms
*Mechanism (engineering), rigid bodies connected by joints in order to accomplish a ...
by which these effects are produced is unknown.
However, 2C-P was found to decrease
dopamine transporter
The dopamine transporter (DAT, also sodium-dependent dopamine transporter) is a membrane-spanning protein coded for in humans by the ''SLC6A3'' gene (also known as ''DAT1''), that pumps the neurotransmitter dopamine out of the synaptic cleft ba ...
(DAT)
expression and to increase DAT
phosphorylation
In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols:
:
This equation can be writ ...
in the
nucleus accumbens
The nucleus accumbens (NAc or NAcc; also known as the accumbens nucleus, or formerly as the ''nucleus accumbens septi'', Latin for ' nucleus adjacent to the septum') is a region in the basal forebrain rostral to the preoptic area of the hypo ...
similarly to
methamphetamine
Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...
in rodents.
Decreased DAT expression may result in reduced
dopamine
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...
reuptake, while DAT phosphorylation is associated with dopamine
reverse transport and
efflux, in turn increasing
extracellular
This glossary of biology terms is a list of definitions of fundamental terms and concepts used in biology, the study of life and of living organisms. It is intended as introductory material for novices; for more specific and technical definitions ...
dopamine levels.
2C-P has also been found to produce
neurotoxicity at high doses in rodents, which appears to be mediated via
neuroinflammation
Neuroinflammation is inflammation of the nervous tissue. It may be initiated in response to a variety of cues, including infection, traumatic brain injury,Ebert SE, Jensen P, Ozenne B, Armand S, Svarer C, Stenbaek DS ''et al.'' Molecular imaging of ...
.
The drug only weakly inhibits the
monoamine oxidase
Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...
s.
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,
or white crystals.
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
Distillation, also classical distillation, is the process of separating the component substances of a liquid mixture of two or more chemically discrete substances; the separation process is realized by way of the selective boiling of the mixt ...
at 100–110 °C at (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
The United Nations (UN) is the Earth, global intergovernmental organization established by the signing of the Charter of the United Nations, UN Charter on 26 June 1945 with the stated purpose of maintaining international peace and internationa ...
'
Convention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February ...
.
Canada
As of October 31, 2016; 2C-P is a controlled substance (Schedule III) in Canada.
China
As of October 2015 2C-P is a controlled substance in China.
Denmark
In Denmark, 2C-P has been added to the list of Schedule B controlled substances.
Finland
Scheduled in "government decree on psychoactive substances banned from the consumer market".
Germany
2C-P is an
Anlage I controlled drug.
Sweden
The
Riksdag
The Riksdag ( , ; also or , ) is the parliament and the parliamentary sovereignty, supreme decision-making body of the Kingdom of Sweden. Since 1971, the Riksdag has been a unicameral parliament with 349 members (), elected proportional rep ...
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.
United Kingdom
2C-P is a
Class A drug in the UK.
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
The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...
by an act of the
US Congress
The United States Congress is the legislature, legislative branch of the federal government of the United States. It is a Bicameralism, bicameral legislature, including a Lower house, lower body, the United States House of Representatives, ...
on July 9, 2012 when US President
Barack Obama
Barack Hussein Obama II (born August 4, 1961) is an American politician who was the 44th president of the United States from 2009 to 2017. A member of the Democratic Party, he was the first African American president in American history. O ...
signed the
Synthetic Drug Abuse Prevention Act of 2012 (SDAPA).
The law came into effect on January 4, 2013.
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
*
2C-Bu
2C-Bu, also known as 2,5-dimethoxy-4-butylphenethylamine, is a chemical compound of the phenethylamine and 2C families. It has been said by Daniel Trachsel to be completely unknown. 2C-Bu is the 2C analogue of the DOx derivative DOBU, which ...
References
External links
2C-P - Isomer Design2C-P - PsychonautWiki2C-P - Erowid2C-P - PiHKAL - Erowid2C-P - PiHKAL - Isomer Design2C-P: The Strongest Member of the 2C Family of Psychedelics - Tripsitter
{{Phenethylamines
5-HT2A agonists
5-HT2B agonists
2C (psychedelics)
Designer drugs
Propyl compounds
Psychedelic phenethylamines
Serotonin receptor agonists
TAAR1 modulators