2C-O-4, also known as 4-isopropoxy-2,5-dimethoxyphenethylamine, is a

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 2C (2C-''x'') is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting ...

. It is also a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

isoproscaline Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is an analog of mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols. It produces hallucinogenic, psychedelic, and entheogenic effects. Chemistry ...

and was probably first synthesized by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

. It produces

hallucinogenic Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, moo ...

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

, 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.2C-O-4 Entry in PiHKAL
/ref> Because of the low potency of 2C-O-4, and the inactivity of

2C-O 2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a chemical compound of the phenethylamine and 2C families. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue o ...

, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further

analogues ''Analogues'' (Spanish: ''Análogos'') is a 2023 Chilean science fiction drama film written, scored and directed by Jorge Olguín. Starring Mónica Carrasco and Jorge Gajardo accompanied by Cindy Díaz. It is about an elderly couple who feel alone ...

Chemistry

2C-O-4 is in a class of compounds commonly known as

s, and the systematic chemical name is 2-(4-isopropoxy-2,5-dimethoxyphenyl)ethanamine.

Effects

Little is known about the

psychopharmacological Psychopharmacology (from Greek ; ; and ) is the scientific study of the effects drugs have on mood, sensation, thinking, behavior, judgment and evaluation, and memory. It is distinguished from neuropsychopharmacology, which emphasizes the corre ...

effects of 2C-O-4. Based on the one report available 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 lists the dosage of 2C-O-4 as being >60 mg.

Pharmacology

The

pharmacology Pharmacology is the science of drugs and medications, including a substance's origin, composition, pharmacokinetics, pharmacodynamics, therapeutic use, and toxicology. More specifically, it is the study of the interactions that occur betwee ...

of 2C-O-4 has been studied.

Dangers

The toxicity of 2C-O-4 is not known.

Legality

Canada

As of October 31, 2016, 2C-O-4 is a controlled substance (Schedule III) in Canada.

United States

2C-O-4 is unscheduled and unregulated 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 ...

; however, because of its close similarity in structure and effects to

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

and

2C-T-7 2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generall ...

, possession and sale of 2C-O-4 may be subject to prosecution under the

Federal Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

References

{{Phenethylamines 2C (psychedelics) Isopropyl compounds Catechol ethers Resorcinol ethers