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2C-C

From Wikipedia, the free encyclopedia
2C-C
Names
Preferred IUPAC name
2-(4-Chloro-2,5-dimethoxyphenyl)ethan-1-amine
Other names
(4-Chloro-2,5-dimethoxyphenethyl)amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: CGKQFIWIPSIVAS-UHFFFAOYSA-N checkY
  • InChI=1/C10H14ClNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
    Key: CGKQFIWIPSIVAS-UHFFFAOYAM
  • COc1cc(CCN)c(cc1Cl)OC
Properties
C10H14ClNO2
Molar mass 215.6778 g/mol
Melting point 220 to 221 °C (428 to 430 °F; 493 to 494 K) (hydrochloride)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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]

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

Effects

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

Pharmacology

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2C-C acts as an agonist of the serotonin 5-HT2 receptors.[3][4] It also binds to the serotonin 5-HT1A receptor with 15-fold lower affinity than for the serotonin 5-HT2A receptor.[3][4] The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition.[4][5] It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.[3][4]

In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.[3][5] It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats.[3][5] These findings suggest that 2C-C may have misuse potential.[3][5] The mechanism by which these effects are produced is unknown.[5] 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.[3][5] 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.[3][5]

2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.[5]

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China

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As of October 2015 2C-C is a controlled substance in China.[6]

Canada

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As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.[7]

Germany

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2C-C is an Anlage I controlled drug.

Sweden

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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.[8]

United States

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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.[9]

Analogues and derivatives

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Analogues and derivatives of 2C-C:

25C-NB*:

N-(2C)-fentanyl:

See also

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References

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  1. ^ a b Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ "S. 3187: Food and Drug Administration Safety and Innovation Act, Subtitle D-Synthetic Drugs". FDA. June 27, 2012. Archived from the original on July 4, 2012. Retrieved July 12, 2012.
  3. ^ a b c d e f g h Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicol Rep. 14: 101890. doi:10.1016/j.toxrep.2025.101890. PMID 39867514.
  4. ^ a b c d Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099.
  5. ^ a b c d e f g h Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, Kim SK, Sung SJ, Kim KM, Kim HC, Lee SY, Jang CG (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Arch Toxicol. 95 (4): 1413–1429. doi:10.1007/s00204-021-02980-x. PMID 33515270.
  6. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  7. ^ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  8. ^ "20050026" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2017-03-24.
  9. ^ "Erowid 2C-C Vault : Legal Status". www.erowid.org. Archived from the original on 2014-06-02.
  10. ^ "Explore N-(2C-C)-Fentanyl | PiHKAL · info". isomerdesign.com.
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