2C (psychedelics) explained

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 coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.

Nomenclature	R3	R4	2D Structure	CAS number
2C-B	H	Br		66142-81-2
2C-Bn	H	CH2C6H5
2C-Bu	H	CH2CH2CH2CH3
2C-C	H	Cl		88441-14-9
2C-C-3 ^[3]	Cl	Cl
2C-CN	H	C≡N		88441-07-0
2C-D	H	CH3		24333-19-5
2C-E	H	CH2CH3		71539-34-9
2C-EF	H	CH2CH2F		1222814-77-8
2C-F	H	F		207740-15-6
2C-G	CH3	CH3		207740-18-9
2C-G-1	CH2
2C-G-2	(CH2)2
2C-G-3	(CH2)3			207740-19-0
2C-G-4	(CH2)4			952006-59-6
2C-G-5	(CH2)5			207740-20-3
2C-G-6	(CH2)6
2C-G-N	(CH)4			207740-21-4
2C-H	H	H		3600-86-0
2C-I	H	I		69587-11-7
2C-iP	H	CH(CH3)2		1498978-47-4
2C-TBU	H	C(CH3)3
2C-CP	H	C3H5		2888537-46-8
2C-CPE	H	C5H9
2C-N	H	NO2		261789-00-8
2C-NH2	H	NH2		168699-66-9
2C-PYR	H	Pyrrolidine
2C-PIP	H	Piperidine
2C-O	H	OCH3		15394-83-9
2C-O-4	H	OCH(CH3)2		952006-65-4
2C-MOM ^[4]	H	CH2OCH3
2C-P	H	CH2CH2CH3		207740-22-5
2C-Ph	H	C6H5
2C-Se	H	Se CH3		1189246-68-1
2C-T	H	SCH3		61638-09-3
2C-T-2	H	SCH2CH3		207740-24-7
2C-T-3^[5]	H	SCH2C(=CH2)CH3		648957-40-8
2C-T-4	H	SCH(CH3)2		207740-25-8
2C-T-5
2C-T-6
2C-T-7	H	S(CH2)2CH3		207740-26-9
2C-T-8	H	SCH2CH(CH2)2		207740-27-0
2C-T-9				207740-28-1
2C-T-10
2C-T-11
2C-T-12
2C-T-13	H	S(CH2)2OCH3		207740-30-5
2C-T-14
2C-T-15	H	SCH(CH2)2
2C-T-16^[6]	H	SCH2CH=CH2		648957-42-0
2C-T-17	H	SCH(CH3)CH2CH3		207740-32-7
2C-T-18
2C-T-19	H	SCH2CH2CH2CH3
2C-T-21	H	S(CH2)2F		207740-33-8
2C-T-21.5				648957-46-4
2C-T-22				648957-48-6
2C-T-23
2C-T-24
2C-T-25
2C-T-27				648957-52-2
2C-T-28				648957-54-4
2C-T-30
2C-T-31
2C-T-32
2C-T-33
2C-T-DFM	H	SCF2H
CYB210010^[7]	H	SCF3
2C-T-DFP	H	SCH2CH2CF2H
2C-T-PARGY	H	SCH2C≡CH
2C-DFM ^[8]	H	CHF2
2C-TFM	H	CF3		159277-08-4
2C-TFE	H	CH2CF3
2C-PFE	H	CF2CF3
2C-PFS	H	SF5
2C-YN	H	C≡CH		752982-24-4
2C-V	H	CH=CH2
2C-AL^[9]	H	CH2CH=CH2

Legality

Canada

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.^[10]

See also

• 25-NB
• Substituted phenethylamines
• Substituted amphetamines
• Substituted methylenedioxyphenethylamines
• DOx
• Substituted tryptamines
• List of miscellaneous 5HT2A agonists

Notes and References

1. Alexander Shulgin, Tania Manning and Paul F Daley. The Shulgin Index. Volume 1. Psychedelic Phenethylamines and Related Compounds. Transform Press, 2011.
2. Daniel Trachsel, David Lehmann and Christoph Enzensperger. Phenethylamine Von der Struktur zur Funktion, pp 762-810. Nachtschatten Verlag AG, 2013.
3. Takahashi M, Nagashima M, Suzuki J, Seto T, Yasuda I, Yoshida T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77(4): 1245–1272.
4. Leth-Petersen S, Petersen IN, Jensen AA, Bundgaard C, Bæk M, Kehler J, Kristensen JL. 5-HT2A/5-HT2C receptor pharmacology and intrinsic clearance of N-benzylphenethylamines modified at the primary site of metabolism. ACS Chem. Neurosci., 16 Nov 2016, 7 (11), 1614–1619.
5. Web site: Shulgin's Sulfur Symphony – Part I. countyourculture. 15 January 2011. 22 October 2017. https://web.archive.org/web/20190919063901/http://countyourculture.com/2011/01/15/shulgins-sulfur-symphony-part-i/. 19 September 2019. dead.
6. Daniel Trachsel . 2003 . Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 2. 4-Thio-substituted [2-(2,5-dimethoxyphenyl)ethyl]amines (=2,5-dimethoxybenzeneethanamines) . . 86 . 7 . 2610–2619 . 10.1002/hlca.200390210.
7. Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, Morgan ME, Reichelt AC, Pathare P, Stang E, Palfreyman MG, Nivorozhkin A. Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist. J Med Chem. 2024 Apr 25;67(8):6144-6188.
8. Book: Daniel Trachsel . David Lehmann . Christoph Enzensperger . amp . 2013 . Phenethylamine: Von der Struktur zur Funktion . Nachtschatten Verlag AG . 978-3-03788-700-4.
9. https://patentscope.wipo.int/search/docs2/pct/WO2022006186/pdf/y_SatokAWjdK--I8ZkJqIVK_Vfz0IETYFMzHZaWlwlu_MA-hS0Wj-9jxUAfgWkQkRy3Rs2NUQ4ZdivqrrDDSaxeMxMgjwmy0MNVSgLhLhgAssl2gRNnZYIXdeBT9Cbko?docId=id00000063934462&filename=WO2022006186-PAMPH-20220106-4462.pdf Kruegel AC. Phenalkylamines and Methods of Treating Mood Disorders. Patent WO 2022/006186
10. Web site: Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) . . 150 . 9 . April 15, 2016 . August 28, 2016.