2C-C

Clinical data
Other names	2,5-Dimethoxy-4-chlorophenethylamine; 4-Chloro-2,5-dimethoxyphenethylamine
Routes of administration	Oral
Drug class	Serotonin5-HT2 receptoragonist;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
PubChemCID	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
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2C-C is apsychedelic drug of the2C family. It was first synthesized byAlexander Shulgin, sometimes used as anentheogen. In his bookPiHKAL (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 isschedule I of section 202(c) of theControlled Substances Act in the United States, signed into law as of July, 2012 under theFood and Drug Administration Safety and Innovation Act.^[2]

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

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

2C-C acts as anagonist of theserotonin5-HT₂ receptors.^[10][5] It also binds to the serotonin5-HT_1A receptor with 15-fold loweraffinity than for the serotonin5-HT_2A receptor.^[10][5] The drug shows little or no affinity for themonoamine transporters (MATs) and shows very weak or negligiblemonoamine reuptake inhibition.^[5][11] It shows high affinity for the rattrace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.^[10][5]

In contrast to many other psychedelics, 2C-C, as well as2C-P and certain 2CNBOMeanalogues, has shownreinforcing effects in rodents.^[10][11] It producesdose-dependentconditioned place preference (CPP) in mice andself-administration in rats.^[10][11] These findings suggest that 2C-C may havemisuse potential.^[10][11] Themechanism by which these effects are produced is unknown.^[11] However, 2C-C was found to decreasedopamine transporter (DAT)expression and to increase DATphosphorylation in thenucleus accumbens andmedial prefrontal cortex (mPFC) similarly tomethamphetamine in rodents.^[10][11] Decreased DAT expression may result in reduceddopaminereuptake, while DAT phosphorylation is associated with dopaminereverse transport andefflux, in turn increasingextracellular dopamine levels.^[10][11]

2C-C has also been found to produceneurotoxicity at high doses in rodents, which appears to be mediated vianeuroinflammation.^[11]

2C drugs like 2C-C are known to bemetabolized by themonoamine oxidase (MAO)enzymesMAO-A andMAO-B.^[12][13]Monoamine oxidase inhibitors (MAOIs) such asphenelzine,tranylcypromine,moclobemide, andselegiline may potentiate the effects of 2C drugs like 2C-C.^[12][13][14] This may result inoverdose and serioustoxicity.^[14][12]

As of October 2015 2C-C is a controlled substance in China.^[15]

As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.^[16]

2C-C is anAnlage I controlled drug.

Sveriges riksdags health ministryStatens folkhälsoinstitut classified 2C-C as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulationSFS 2005:26 listed as2,5-dimetoxi-4-klorfenetylamin (2C-C), making it illegal to sell or possess.^[17]

As of July 9, 2012, in theUnited States 2C-C is aSchedule I substance under theFood and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal.^[18]

• Phenethylamines
• DOC

• Erowid 2C-C Vault
• pihkal.info: 2C-C

• 2C (psychedelics)
• 5-HT2A agonists
• 5-HT2B agonists
• 5-HT2C agonists
• Chlorobenzene derivatives
• Designer drugs
• TAAR1 modulators

• CS1 Chinese-language sources (zh)
• Articles with short description
• Short description is different from Wikidata
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Drugs missing an ATC code