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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 more potent and more metabolically stable and longer acting compounds.

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.

Pharmacology

Pharmacodynamics

The 2C drugs act as agonists of the serotonin 5-HT₂ receptors, including of the serotonin 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors. Most of the 2C drugs have much lower affinity for the serotonin 5-HT_1A receptor than for the serotonin 5-HT_2A receptor. Their psychedelic effects are thought to be mediated specifically by activation of the serotonin 5-HT_2A receptor.

Unlike many other phenethylamines, 2C drugs, including 2C-C, 2C-D, 2C-E, 2C-I, and 2C-T-2 among others, are inactive as monoamine releasing agents and reuptake inhibitors.

Many of the 2C drugs are agonists of the rat, mouse, and/or human trace amine-associated receptor 1 (TAAR1).

Pharmacokinetics

The 2C drugs are orally active and most have doses in the range of 10 to 60 mg and durations in the range of 4 to 12 hours. They are metabolized by O-demethylation and deamination (by monoamine oxidases).

List of 2C drugs

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	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	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	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	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	H	SCF3
2C-T-DFP	H	SCH2CH2CF2H
2C-T-PARGY	H	SCH2C≡CH
2C-DFM	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	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.

See also

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

References

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• 2C (psychedelics)
• Chemical classes of psychoactive drugs
• Phenethylamines