2C (psychedelics)

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.^[1] Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds.^[2] Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book PiHKAL (Phenethylamines i Have Known And Loved). Shulgin also invented the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.^[3]

General structure of a 2C compound

Nomenclature	R3	R4	2D Structure	3D Structure
2C-B	H	Br
2C-Bn	H	CH2C6H5
2C-Bu	H	CH2CH2CH2CH3
2C-C	H	Cl
2C-CN	H	C≡N
2C-CP	H	C3H5
2C-D	H	CH3
2C-E	H	CH2CH3
2C-EF	H	CH2CH2F
2C-F	H	F
2C-G	CH3	CH3
2C-G-3	(CH2)3
2C-G-4	(CH2)4
2C-NPH	(CH)4
2C-H	H	H
2C-I	H	I
2C-N	H	NO2
2C-NH2	H	NH2
2C-O	H	OCH3
2C-O-4	H	OCH(CH3)2
2C-P	H	CH2CH2CH3
2C-iP	H	CH(CH3)2
2C-Ph	H	C6H5
2C-SE	H	Se CH3
2C-T	H	SCH3
2C-T-2	H	SCH2CH3
2C-T-4	H	SCH(CH3)2
2C-T-7	H	S(CH2)2CH3
2C-T-8	H	SCH2CH(CH2)2
2C-T-9	H	SC(CH3)3
2C-T-13	H	S(CH2)2OCH3
2C-T-15	H	SCH(CH2)2
2C-T-16	H	SCH2CH=CH2
2C-T-17	H	SCH(CH3)CH2CH3
2C-T-21	H	S(CH2)2F
2C-TFM	H	CF3
2C-TFE	H	CH2CF3
2C-YN	H	C≡CH
2C-V	H	CH=CH2

Legality

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.^[4]

See also

• Substituted phenethylamines
• Substituted amphetamines
• Substituted methylenedioxyphenethylamines
• DOx and 3Cs
• Substituted tryptamines

References

1. Alexander Shulgin, Tania Manning and Paul F Daley. The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press, 2011. ISBN 978-0-9630096-3-0
2. Daniel Trachsel, David Lehmann and Christoph Enzensperger. Phenethylamine Von der Struktur zur Funktion, pp 762-810. Nachtschatten Verlag AG, 2013. ISBN 978-3-03788-700-4
3. Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
4. "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. April 15, 2016. Retrieved August 28, 2016.