2,4,5-Trimethoxyphenethylamine (2C-O or 2C-OMe) or 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 am ...

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 in ...

and was first synthesized by Jansen in 1931. It is a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term met ...

of the drug

mescaline Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological ...

(3,4,5-tri

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position ...

Chemistry

2C-O is a member of a class of

chemical compounds A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

commonly known as

s. Its full chemical name is 2-(2,4,5-trimethoxyphenyl)ethanamine; it is also known as 2,4,5-trimethoxyphenethylamine and 2,4,5-TMPEA.

Effects

Although not centrally active itself, 2C-O appeared to potentiate the action of mescaline when employed as pretreatment 45 minutes prior to the administration of mescaline.

Dangers

The toxicity of 2C-O is not known.

Law

Canada

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

United States

2C-O is a

Schedule I Schedule 1 may refer to: * Schedule I Controlled Substances within the US Controlled Substances Act * Schedule I Controlled Drugs and Substances within the Canadian Controlled Drugs and Substances Act * Schedule I Psychotropic Substances within th ...

substance, as a positional isomer of

United Kingdom

2C-O and all other compounds featured in PiHKAL are

Class A drug These drugs are known in the UK as ''controlled drugs'', because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other dru ...

s in the United Kingdom.

References

External links

2C-O Entry in PiHKALTMPEA Entry in PiHKAL • info
{{DEFAULTSORT:Trimethoxyphenethylamine, 2,4,5- 2C (psychedelics)