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2C-C

From Wikipedia, the free encyclopedia
Pharmaceutical compound
2C-C
Clinical data
Other names2,5-Dimethoxy-4-chlorophenethylamine; 4-Chloro-2,5-dimethoxyphenethylamine
Routes of
administration
Oral
Drug classSerotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen
Legal status
Legal status
Identifiers
  • 2-(4-chloro-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H14ClNO2
Molar mass215.68 g·mol−1
3D model (JSmol)
Melting point220 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 checkY
  • Key:CGKQFIWIPSIVAS-UHFFFAOYSA-N checkY
  (verify)

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.

Effects

[edit]

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

Pharmacology

[edit]
2C-C activities
TargetAffinity (Ki, nM)
5-HT1A190–740 (Ki)
>10,000 (EC50Tooltip half-maximal effective concentration)
<25% (EmaxTooltip maximal efficacy)
5-HT1B5-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-HT35-HT7ND
α1A13,000
α1B,α1DND
α2A530
α2B,α2CND
β1β3ND
D113,000
D22,100
D317,000
D4ND
D5ND
H114,000
H2H4ND
M1M5ND
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:[3][4][5][6][7][8][9]

2C-C acts as anagonist of theserotonin5-HT2 receptors.[10][5] It also binds to the serotonin5-HT1A receptor with 15-fold loweraffinity than for the serotonin5-HT2A 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]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

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]

Legal status

[edit]

China

[edit]

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

Canada

[edit]

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

Germany

[edit]

2C-C is anAnlage I controlled drug.

Sweden

[edit]

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]

United States

[edit]

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]

Analogues and derivatives

[edit]

Analogues and derivatives of2C-C:

25C-NB*:

N-(2C)-fentanyl:

See also

[edit]

References

[edit]
  1. ^abShulgin, 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. RetrievedJuly 12, 2012.
  3. ^"Kᵢ Database".PDSP. 16 March 2025. Retrieved16 March 2025.
  4. ^Liu, Tiqing."BindingDB BDBM50240789 2-(4-Chloro-2,5-dimethoxy-phenyl)-ethylamine::2-(4-chloro-2,5-dimethoxyphenyl)ethylamine::CHEMBL124733".BindingDB. Retrieved16 March 2025.
  5. ^abcdeRickli 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.
  6. ^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.
  7. ^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.
  8. ^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.
  9. ^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.
  10. ^abcdefghGil-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.
  11. ^abcdefghKim 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.
  12. ^abcDean 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.
  13. ^abTheobald 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.
  14. ^abHalman 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.
  15. ^"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 fromthe original on 1 October 2015. Retrieved1 October 2015.
  16. ^"Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  17. ^"20050026"(PDF).Archived(PDF) from the original on 2013-09-29. Retrieved2017-03-24.
  18. ^"Erowid 2C-C Vault : Legal Status".www.erowid.org.Archived from the original on 2014-06-02.
  19. ^"Explore N-(2C-C)-Fentanyl | PiHKAL · info".isomerdesign.com.

External links

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Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages.See also:Receptor/signaling modulators
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