2C-C

Last updated

2C-C
2C-C.svg
2C-C-3d-sticks.png
Clinical data
Other names2,5-Dimethoxy-4-chlorophenethylamine; 4-Chloro-2,5-dimethoxyphenethylamine
Routes of
administration 		Oral [1]
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action 1.5–2 hours [1]
Duration of action 4–8 hours [1]
Identifiers
  • 2-(4-chloro-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.218.153 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H14ClNO2
Molar mass 215.68 g·mol−1
3D model (JSmol)
Melting point 220 to 221 °C (428 to 430 °F) (hydrochloride)
  • COc1cc(CCN)c(cc1Cl)OC
  • 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 Yes check.svgY
  • Key:CGKQFIWIPSIVAS-UHFFFAOYSA-N Yes check.svgY
   (verify)

2C-C, also known as 4-chloro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. [1] It is taken orally. [1]

Contents

2C-C was first described in the scientific literature by Alice Cheng and Neal Castagnoli in 1984. [2] It was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1] The drug 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. [3]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-C's dose range as 20 to 40 mg orally and its duration as 4 to 8 hours. [1] Its onset is described as delayed compared to 2C-B and as being 1.5 to 2 hours. [1] In addition to oral administration, a single report of 20 mg by intravenous injection was described as overwhelming, with effects peaking after 5 minutes and lasting perhaps 15 minutes. [1] The effects of 2C-C have been reported to include psychedelic visuals, sensual enhancement, stimulation, sedation, and relaxation, among others. [1] Its stimulating effects are said to be less than those of 2C-B and it is said to be sedating in some ways. [1]

Interactions

2C drugs like 2C-C are known to be metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. [4] [5] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-C. [4] [5] [6] This may result in overdose and serious toxicity. [6] [4]

Pharmacology

Pharmacodynamics

2C-C activities
Target Affinity (Ki, nM)
5-HT1A 190–740 (Ki)
>10,000 (EC50 Tooltip half-maximal effective concentration)
<25% (Emax Tooltip 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
TAAR1 Tooltip Trace amine-associated receptor 14,100 (Ki) (mouse)
110 (Ki) (rat)
2,300 (EC50) (mouse)
340 (EC50) (rat)
>10,000 (EC50) (human)
57% (Emax) (mouse)
51% (Emax) (rat)
SERT Tooltip Serotonin transporter24,000 (Ki)
72,000–74,000 (IC50 Tooltip half-maximal inhibitory concentration)
>100,000 (EC50) (rat)
NET Tooltip Norepinephrine transporter>30,000 (Ki)
63,000–93,000 (IC50)
100,000 (EC50) (rat)
DAT Tooltip Dopamine transporter>30,000 (Ki)
305,000 (IC50)
>100,000 (EC50) (rat)
MAO-A Tooltip Monoamine oxidase AND (IC50)
MAO-B Tooltip Monoamine oxidase BND (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [7] [8] [9] [10] [11] [12] [13] [14]

2C-C acts as an agonist of the serotonin 5-HT2 receptors. [15] [9] It also binds to the serotonin 5-HT1A receptor with 15-fold lower affinity than for the serotonin 5-HT2A receptor. [15] [9] The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition. [9] [16] It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1. [15] [9]

In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents. [15] [16] It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats. [15] [16] These findings suggest that 2C-C may have misuse potential. [15] [16] The mechanism by which these effects are produced is unknown. [16] 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. [15] [16] 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. [15] [16]

2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation. [16]

Chemistry

Synthesis

The chemical synthesis of 2C-C has been described. [1]

Analogues

Analogues of 2C-C include 2C-B, 2C-I, DOC, and 25C-NBOMe, among others. [1] [17]

History

2C-C was first described in the scientific literature by Alice Cheng and Neal Castagnoli in 1984. [2] It was described in greater detail, including its properties and effects in humans, by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1]

Society and culture

China

As of October 2015 2C-C is a controlled substance in China. [18]

Canada

As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada. [19]

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market". [20]

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. [21]

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. [22]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. "2C-C".
  2. 1 2 Cheng AC, Castagnoli N (April 1984). "Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogues of 6-hydroxydopamine". Journal of Medicinal Chemistry. 27 (4): 513–520. doi:10.1021/jm00370a014. PMID   6423824.
  3. ↑ "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.
  4. 1 2 3 Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". Journal of Medical Toxicology. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC   3657019 . PMID   23494844.
  5. 1 2 Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochemical Pharmacology. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID   17067556.
  6. 1 2 Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  7. ↑ "Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025.
  8. ↑ Liu T. "BindingDB BDBM50240789 2-(4-Chloro-2,5-dimethoxy-phenyl)-ethylamine::2-(4-chloro-2,5-dimethoxyphenyl)ethylamine::CHEMBL124733". BindingDB. Retrieved 16 March 2025.
  9. 1 2 3 4 5 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)". Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  10. ↑ Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (March 2014). "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function". Psychopharmacology. 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC   3945162 . PMID   24142203.
  11. ↑ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID   17223101.
  12. ↑ Rudin D, Luethi D, Hoener MC, Liechti ME (2022). "Structure-activity Relation of Halogenated 2,5-Dimethoxyamphetamines Compared to their α‑Desmethyl (2C) Analogues". The FASEB Journal. 36 (S1) fasebj.2022.36.S1.R2121. doi: 10.1096/fasebj.2022.36.S1.R2121 . ISSN   0892-6638.
  13. ↑ Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Archives of Toxicology. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl: 1854/LU-8687071 . PMID   32627074.
  14. ↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1" (PDF). The Journal of Pharmacology and Experimental Therapeutics. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601. Archived from the original (PDF) on 2025-05-09.
  15. 1 2 3 4 5 6 7 8 Gil-Martins E, Barbosa DJ, Borges F, Remião F, Silva R (June 2025). "Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?". Toxicology Reports. 14 101890. Bibcode:2025ToxR...1401890G. doi:10.1016/j.toxrep.2025.101890. PMC   11762925 . PMID   39867514.
  16. 1 2 3 4 5 6 7 8 Kim YJ, Ma SX, Hur KH, Lee Y, Ko YH, Lee BR, et al. (April 2021). "New designer phenethylamines 2C-C and 2C-P have abuse potential and induce neurotoxicity in rodents". Archives of Toxicology. 95 (4): 1413–1429. Bibcode:2021ArTox..95.1413K. doi:10.1007/s00204-021-02980-x. PMID   33515270.
  17. ↑ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  18. ↑ "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.
  19. ↑ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  20. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" . Retrieved 2025-09-09.
  21. ↑ "20050026" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2017-03-24.
  22. ↑ "Erowid 2C-C Vault : Legal Status". www.erowid.org. Archived from the original on 2014-06-02.
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