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2C-C
Chemical compound

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. 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.

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

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Effects

Over the approximate dose range 20–40 mg, visual effects last approximately 4 to 8 hours.3

Pharmacology

2C-C activities
TargetAffinity (Ki, nM)
5-HT1A190–740 (Ki)>10,000 (EC50Tooltip half-maximal effective concentration)<25% (EmaxTooltip maximal efficacy)
5-HT1B–5-HT1FND
5-HT2A5.47–13 (Ki)9.27–200 (EC50)49–102% (Emax)
5-HT2BND (Ki)280 (EC50)81% (Emax)
5-HT2C5.4–90 (Ki)24.2 (EC50)94% (Emax)
5-HT3–5-HT7ND
α1A13,000
α1B, α1DND
α2A530
α2B, α2CND
β1–β3ND
D113,000
D22,100
D317,000
D4ND
D5ND
H114,000
H2–H4ND
M1–M5ND
I1ND
σ1, σ2ND
TAAR1Tooltip 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)
SERTTooltip Serotonin transporter24,000 (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 AND (IC50)
MAO-BTooltip 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: 45678910

2C-C acts as an agonist of the serotonin 5-HT2 receptors.1112 It also binds to the serotonin 5-HT1A receptor with 15-fold lower affinity than for the serotonin 5-HT2A receptor.1314 The drug shows little or no affinity for the monoamine transporters (MATs) and shows very weak or negligible monoamine reuptake inhibition.1516 It shows high affinity for the rat trace amine-associated receptor 1 (TAAR1), but only weak affinity for the mouse TAAR1.1718

In contrast to many other psychedelics, 2C-C, as well as 2C-P and certain 2C NBOMe analogues, has shown reinforcing effects in rodents.1920 It produces dose-dependent conditioned place preference (CPP) in mice and self-administration in rats.2122 These findings suggest that 2C-C may have misuse potential.2324 The mechanism by which these effects are produced is unknown.25 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.2627 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.2829

2C-C has also been found to produce neurotoxicity at high doses in rodents, which appears to be mediated via neuroinflammation.30

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.3132 Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs like 2C-C.333435 This may result in overdose and serious toxicity.3637

China

As of October 2015 2C-C is a controlled substance in China.38

Canada

As of October 31, 2016; 2C-C is a controlled substance (Schedule III) in Canada.39

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.40

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.41

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

N-(2C)-fentanyl:

  • N-(2C-C)-fentanyl42

See also

References

  1. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 0-9630096-0-5 ↩

  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. https://www.govtrack.us/congress/bills/112/s3187/text ↩

  3. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 0-9630096-0-5 ↩

  4. "Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025. https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14697&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=14669&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= ↩

  5. Liu, Tiqing. "BindingDB BDBM50240789 2-(4-Chloro-2,5-dimethoxy-phenyl)-ethylamine::2-(4-chloro-2,5-dimethoxyphenyl)ethylamine::CHEMBL124733". BindingDB. Retrieved 16 March 2025. https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50240789 ↩

  6. 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. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  7. 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" (PDF). Psychopharmacology (Berl). 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC 3945162. PMID 24142203. https://www.researchgate.net/profile/Michael-Forster-2/publication/258061356_Behavioral_and_neurochemical_pharmacology_of_six_psychoactive_substituted_phenethylamines_Mouse_locomotion_rat_drug_discrimination_and_in_vitro_receptor_and_transporter_binding_and_function/links/53d119a00cf2f7e53cfbcd68/Behavioral-and-neurochemical-pharmacology-of-six-psychoactive-substituted-phenethylamines-Mouse-locomotion-rat-drug-discrimination-and-in-vitro-receptor-and-transporter-binding-and-function.pdf ↩

  8. Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=00665d67c36dcf1777989b70cc901c654420a0c7 ↩

  9. 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". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl:1854/LU-8687071. PMID 32627074. /wiki/Bibcode_(identifier) ↩

  10. 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". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601. /wiki/Doi_(identifier) ↩

  11. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  12. 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. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  13. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  14. 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. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  15. 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. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  16. 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. /wiki/Doi_(identifier) ↩

  17. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  18. 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. https://psilosybiini.info/paperit/Receptor%20interaction%20profiles%20of%20novel%20N-2-methoxybenzyl%20(NBOMe)%20derivatives%20of%202,5-dimethoxy-substituted%20phenethylamines%20(2C%20drugs)%20(Rickli%20et%20al.,%202015).pdf ↩

  19. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  20. 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. /wiki/Doi_(identifier) ↩

  21. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  22. 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. /wiki/Doi_(identifier) ↩

  23. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  24. 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. /wiki/Doi_(identifier) ↩

  25. 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. /wiki/Doi_(identifier) ↩

  26. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  27. 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. /wiki/Doi_(identifier) ↩

  28. 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. PMC 11762925. PMID 39867514. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11762925 ↩

  29. 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. /wiki/Doi_(identifier) ↩

  30. 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. /wiki/Doi_(identifier) ↩

  31. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019 ↩

  32. 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)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. /wiki/Doi_(identifier) ↩

  33. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019 ↩

  34. 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)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID 17067556. /wiki/Doi_(identifier) ↩

  35. Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641 ↩

  36. Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10851641 ↩

  37. Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC 3657019. PMID 23494844. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3657019 ↩

  38. "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. https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html ↩

  39. "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php ↩

  40. "20050026" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2017-03-24. https://www.notisum.se/rnp/sls/sfs/20050026.pdf ↩

  41. "Erowid 2C-C Vault : Legal Status". www.erowid.org. Archived from the original on 2014-06-02. http://www.erowid.org/chemicals/2cc/2cc_law.shtml ↩

  42. "Explore N-(2C-C)-Fentanyl | PiHKAL · info". isomerdesign.com. https://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=14010 ↩