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3-Chlorocathinone

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3-Chlorocathinone
Clinical data
Other names3-CC; Norclophedrone; 3Cl-C; 3Cl-Cathinone; 3-Chloro-β-ketoamphetamine
Drug classStimulant; Serotonin–norepinephrine–dopamine releasing agent
Identifiers
IUPAC name
  • 2-amino-1-(3-chlorophenyl)propan-1-one
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC9H10ClNO
Molar mass183.64 g·mol
3D model (JSmol)
SMILES
  • CC(C(=O)C1=CC(=CC=C1)Cl)N
InChI
  • InChI=1S/C9H10ClNO/c1-6(11)9(12)7-3-2-4-8(10)5-7/h2-6H,11H2,1H3
  • Key:RDWWHMAISJGIDU-UHFFFAOYSA-N

3-Chlorocathinone (3-CC) is a psychostimulant drug of the cathinone family. It is the analogue of the antidepressant bupropion in which the N-tert-butyl group has been removed. The drug is also the analogue of the stimulant 3-chloromethcathinone (3-CMC; clophedrone) in which the N-methyl group has been removed.

3-CC is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA). Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release are 64 nM for dopamine, 105 nM for norepinephrine, and 567 nM for serotonin in rat brain synaptosomes. Hence, 3-CC shows almost 10-fold preference for induction of dopamine release over induction of serotonin release.

The drug was encountered as a novel designer and recreational drug by 2020.

References

  1. ^ Mazzoni, Irene; Rabin, Olivier (2024). "NPS, PEDs and other emerging drugs on the Clearnet and the Darkweb: Use in sport". Emerging Trends in Drugs, Addictions, and Health. 4: 100148. doi:10.1016/j.etdah.2024.100148.
  2. ^ Pulver B, Fischmann S, Gallegos A, Christie R (December 2024). "EMCDDA framework and practical guidance for naming cathinones". Drug Test Anal. 16 (12): 1409–1435. doi:10.1002/dta.3662. PMC 11635063. PMID 38389255.
  3. ^ Shalabi AR, Walther D, Baumann MH, Glennon RA (June 2017). "Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release". ACS Chem Neurosci. 8 (6): 1397–1403. doi:10.1021/acschemneuro.7b00055. PMC 7261150. PMID 28220701.
  4. ^ Shalabi, Abdelrahman R. (14 December 2017). Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters. VCU Scholars Compass (Thesis). doi:10.25772/M4E1-3549. Retrieved 24 November 2024.
  5. Glennon RA (2014). "Bath salts, mephedrone, and methylenedioxypyrovalerone as emerging illicit drugs that will need targeted therapeutic intervention". Adv Pharmacol. 69: 581–620. doi:10.1016/B978-0-12-420118-7.00015-9. PMC 4471862. PMID 24484988. Bupropion, the N-tert-butyl analog of 3-chlorocathinone, is a clinically employed antidepressant.


Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Monoamine releasing agents
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulatorsMonoamine reuptake inhibitorsAdrenergicsDopaminergicsSerotonergicsMonoamine metabolism modulatorsMonoamine neurotoxins
Phenethylamines
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous


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