2,4,5-Trimethoxyphenethylamine

2,4,5-Trimethoxyphenethylamine (2C-O or 2C-OMe) or is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline (3,4,5-trimethoxy).

2,4,5-Trimethoxyphenethylamine
Names
Preferred IUPAC name
2-(2,4,5-Trimethoxyphenyl)ethan-1-amine
Other names
2C-O; 2C-OMe; 2,4,5-TMPEA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C11H17NO3/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3 Y
    Key: GKATTZLSNLYADI-UHFFFAOYSA-N Y
  • InChI=1/C11H17NO3/c1-13-9-7-11(15-3)10(14-2)6-8(9)4-5-12/h6-7H,4-5,12H2,1-3H3
    Key: GKATTZLSNLYADI-UHFFFAOYAA
  • O(c1cc(c(OC)cc1OC)CCN)C
Properties
C11H17NO3
Molar mass 211.261 g·mol−1
Melting point 187 to 188 °C (369 to 370 °F; 460 to 461 K)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Chemistry

2C-O is a member of a class of chemical compounds commonly known as phenethylamines. 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.[1]

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.[2]

United States

2C-O is a Schedule I substance, as a positional isomer of mescaline.

United Kingdom

2C-O and all other compounds featured in PiHKAL are Class A drugs in the United Kingdom.

References
  1. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. Government of Canada, Public Works and Government Services Canada (May 4, 2016). "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". gazette.gc.ca.
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