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 coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.^[3]

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 [4]	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 [5]	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[6]	H	SCH2C(=CH2)CH3		648957-40-8
2C-T-4	H	SCH(CH3)2		207740-25-8
2C-T-5[6]
2C-T-6[6]
2C-T-7	H	S(CH2)2CH3		207740-26-9
2C-T-8	H	SCH2CH(CH2)2		207740-27-0
2C-T-9[6]				207740-28-1
2C-T-10[6]
2C-T-11[6]
2C-T-12[6]
2C-T-13	H	S(CH2)2OCH3		207740-30-5
2C-T-14[6]
2C-T-15	H	SCH(CH2)2
2C-T-16[7]	H	SCH2CH=CH2		648957-42-0
2C-T-17	H	SCH(CH3)CH2CH3		207740-32-7
2C-T-18[6]
2C-T-19	H	SCH2CH2CH2CH3
2C-T-21	H	S(CH2)2F		207740-33-8
2C-T-21.5[6]				648957-46-4
2C-T-22[6]				648957-48-6
2C-T-23[6]
2C-T-24[6]
2C-T-25[6]
2C-T-27[6]				648957-52-2
2C-T-28[6]				648957-54-4
2C-T-30[6]
2C-T-31[6]
2C-T-32[6]
2C-T-33[6]
2C-T-DFM	H	SCF2H
CYB210010[8]	H	SCF3
2C-T-DFP	H	SCH2CH2CF2H
2C-T-PARGY	H	SCH2C≡CH
2C-DFM [9]: 770	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[10]	H	CH2CH=CH2

As of October 12, 2016, the 2C-x family of substituted phenethylamines is a controlled substance (Schedule III) in Canada.^[11]

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