2C-C

2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated.^[1] 2C-C is schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July, 2012 under the Food and Drug Administration Safety and Innovation Act.^[2]

2C-C

Clinical data
Other names	2,5-Dimethoxy-4-chlorophenethylamine; 4-Chloro-2,5-dimethoxyphenethylamine
Routes of administration	Oral
Drug class	Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) CA: Schedule III DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name 2-(4-chloro-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number	88441-14-9 Y
PubChem CID	29979100
ChemSpider	21106221 Y
UNII	0RO7MZY2LS
ChEMBL	ChEMBL124733 Y
CompTox Dashboard (EPA)	DTXSID80893699
Chemical and physical data
Formula	C10H14ClNO2
Molar mass	215.68 g·mol−1
3D model (JSmol)	Interactive image
Melting point	220 to 221 °C (428 to 430 °F) (hydrochloride)
SMILES COc1cc(CCN)c(cc1Cl)OC
InChI InChI=1S/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 Y Key:CGKQFIWIPSIVAS-UHFFFAOYSA-N Y
(verify)

Not much information is known about the toxicity of 2C-C.

Effects

Over the approximate dose range 20–40 mg, visual effects last approximately 4 to 8 hours.^[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

2C drugs like 2C-C are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.^[3][4] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-C.^[3][4][5] This may result in overdose and serious toxicity.^[5][3]

Pharmacology

2C-C activities

Target	Affinity (Ki, nM)
5-HT1A	190–740 (Ki) >10,000 (EC50Tooltip half-maximal effective concentration) <25% (EmaxTooltip maximal efficacy)
5-HT1B	ND
5-HT1D	ND
5-HT1E	ND
5-HT1F	ND
5-HT2A	5.47–13 (Ki) 9.27–200 (EC50) 49–102% (Emax)
5-HT2B	ND (Ki) 280 (EC50) 81% (Emax)
5-HT2C	5.4–90 (Ki) 24.2 (EC50) 94% (Emax)
5-HT3	ND
5-HT4	ND
5-HT5A	ND
5-HT6	ND
5-HT7	ND
α1A	13,000
α1B, α1D	ND
α2A	530
α2B, α2C	ND
β1–β3	ND
D1	13,000
D2	2,100
D3	17,000
D4	ND
D5	ND
H1	14,000
H2–H4	ND
M1–M5	ND
I1	ND
σ1, σ2	ND
TAAR1Tooltip Trace amine-associated receptor 1	4,100 (Ki) (mouse) 110 (Ki) (rat) 2,300 (EC50) (mouse) 340 (EC50) (rat) >10,000 (EC50) (human) 57% (Emax) (mouse) 51% (Emax) (rat)
SERTTooltip Serotonin transporter	24,000 (Ki) 72,000–74,000 (IC50Tooltip half-maximal inhibitory concentration) >100,000 (EC50) (rat)
NETTooltip Norepinephrine transporter	>30,000 (Ki) 63,000–93,000 (IC50) 100,000 (EC50) (rat)
DATTooltip Dopamine transporter	>30,000 (Ki) 305,000 (IC50) >100,000 (EC50) (rat)
MAO-ATooltip Monoamine oxidase A	ND (IC50)
MAO-BTooltip Monoamine oxidase B	ND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [6][7][8][9][10][11][12][13]

2C-C acts as an agonist of the serotonin 5-HT₂ receptors.^[14][8] It also binds to the serotonin 5-HT_1A receptor with 15-fold lower affinity than for the serotonin 5-HT_2A receptor.^[14][8] The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition.^[8][15] It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.^[14][8]

In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.^[14][15] It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats.^[14][15] These findings suggest that 2C-C may have misuse potential.^[14][15] The mechanism by which these effects are produced is unknown.^[15] However, 2C-C was found to decrease dopamine transporter (DAT) expression and to increase DAT phosphorylation in the nucleus accumbens and medial prefrontal cortex (mPFC) similarly to methamphetamine in rodents.^[14][15] Decreased DAT expression may result in reduced dopamine reuptake, while DAT phosphorylation is associated with dopamine reverse transport and efflux, in turn increasing extracellular dopamine levels.^[14][15]

2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.^[15]

Chemistry

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

• 25C-NBF
• 25C-NBMD
• 25C-NBOH
• 25C-NBOMe (NBOMe-2CC)
• 25C-NB3OMe
• 25C-NB4OMe

N-(2C)-fentanyl:

• N-(2C-C)-fentanyl^[16]

Society and culture

Legal status

China

As of October 2015 2C-C is a controlled substance in China.^[17]

Canada

As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.^[18]

Germany

2C-C is an Anlage I controlled drug.

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-C as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as 2,5-dimetoxi-4-klorfenetylamin (2C-C), making it illegal to sell or possess.^[19]

United States

As of July 9, 2012, in the United States 2C-C is a Schedule I substance under the Food and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal.^[20]

See also

• Phenethylamines
• DOC