4-Chloroethcathinone

4-Chloroethcathinone
Clinical data
Other names4-CEC; 4-Chloro-N-ethylcathinone; 4′-Chloro-2-(ethylamino)propanophenone; 4Cl-EC; SKF-70948; SKF70948; SK&F-70948; FWH-494; FWH494
Drug classStimulant; Entactogen; Serotonin releasing agent or serotonin–dopamine releasing agent
ATC code
  • None
Identifiers
  • 1-(4-chlorophenyl)-2-(ethylamino)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H14ClNO
Molar mass211.69 g·mol−1
3D model (JSmol)
  • CCNC(C)C(=O)C1=CC=C(C=C1)Cl
  • InChI=1S/C11H14ClNO/c1-3-13-8(2)11(14)9-4-6-10(12)7-5-9/h4-8,13H,3H2,1-2H3
  • Key:RNBCGEIZCHBTGL-UHFFFAOYSA-N

4-Chloroethcathinone (4-CEC) is an organic chemical compound that is classified as substituted cathinone a stimulant and also probably entactogen. Like other 4-chlorocathinones, it may have the potential for abuse in humans and cause adverse effects similar to those associated with mephedrone. 4-CEC was encountered as a novel designer drug in Europe in 2016.

Pharmacology

Pharmacodynamics

In studies evaluating rat brain synaptosomes in vitro, 4-CEC demonstrated a strong preference for interacting with the serotonin transporter (SERT) over the dopamine transporter (DAT) and norepinephrine transporter (NET). It acts as a moderate SERT reuptake inhibitor and weak reuptake inhibitor at DAT and NET, while functioning as a substrate at SERT. It behaves primarily as a serotonin-releasing agent with weak norepinephrine release profile. In another study however, 4-CEC was a well-balanced serotonin–dopamine releasing agent (SDRA).

The specific values obtained in the rat synaptosome:

  • Monoamine reuptake inhibition:
    • DAT IC50: 1,455–1,574 nM
    • NET IC50: 2,848–3,055 nM
    • SERT IC50: 579–589 nM
  • Monoamine release kinetics:
    • DAT EC50: 354 nM or inactive
    • NET EC50: 3,058–5,194 nM (Emax = 81%)
    • SERT EC50: 153–191 ± 26 nM (Emax = 107%)

4-CEC has been reported to produce hyperlocomotion, a stimulant-like effect, in rodents. It has also been found to fully substitute for methamphetamine and cocaine in rodent drug discrimination tests, further suggesting stimulant-like effects. In addition, the drug has been found to fully substitute for MDMA in rodent drug discrimination tests, suggesting entactogen-like effects as well.

Pharmacokinetics

In vivo studies show that 4-CEC is characterized by rapid absorption (Tmax approx. 10 minutes) and quick elimination from plasma (a half-life, t1/2, of approx. 100 minutes).

Tissue distribution profiles indicates that 4-CEC accumulates primarily in the brain, lungs, kidneys, and liver. It is also characterized by multi-organ toxicity.

Chemistry

Analogues

Analogues of 4-CEC include 4-chlorocathinone (4-CC), 4-chloromethcathinone (4-CMC; clephedrone), 4-chloro-α-pyrrolidinopropiophenone (4-CαPPP), 4-chloroethamphetamine (4-CEA), and mephedrone (4-MMC), among others.

History

4-CEC was encountered as a novel designer drug in Sweden in January 2016.

Society and culture

In Poland, the possession of 4-CEC is prohibited by law; the substance is included in the list of new psychoactive substances (NPS).

See also

References

  1. 1 2 3 Chen S, Zhou W, Lai M (March 2024). "Synthetic Cathinones: Epidemiology, Toxicity, Potential for Abuse, and Current Public Health Perspective". Brain Sciences. 14 (4): 334. doi:10.3390/brainsci14040334. PMC 11048581. PMID 38671986.
  2. 1 2 3 4 5 Chojnacki MR, Thorndike EB, Partilla JS, Rice KC, Schindler CW, Baumann MH (June 2023). "Neurochemical and Cardiovascular Effects of 4-Chloro Ring-Substituted Synthetic Cathinones in Rats". The Journal of Pharmacology and Experimental Therapeutics. 385 (3): 162–170. doi:10.1124/jpet.122.001478. PMC 10201577. PMID 36669877.
  3. 1 2 3 4 5 Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, et al. (March 2024). "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology. 245 109827. doi:10.1016/j.neuropharm.2023.109827. PMC 10842458. PMID 38154512.
  4. 1 2 3 4 Gatch MB, Shetty RA, Sumien N, Forster MJ (July 2021). "Behavioral effects of four novel synthetic cathinone analogs in rodents". Addiction Biology. 26 (4) e12987. doi:10.1111/adb.12987. PMC 11590110. PMID 33155384.
  5. 1 2 Pulver B, Fischmann S, Gallegos A, Christie R (December 2024). "EMCDDA framework and practical guidance for naming cathinones". Drug Testing and Analysis. 16 (12): 1409–1435. doi:10.1002/dta.3662. PMC 11635063. PMID 38389255.
  6. 1 2 "I Background to this report". Archived from the original on 2026-03-10. Retrieved 2026-10-31.
  7. 1 2 Wang Y, Yang Y, Zhan Y, Yin J, Zhou X, Xu C, et al. (September 2023). "Pharmacokinetics and metabolomics of the new psychoactive substance 4-chloroethylcathinone". Arabian Journal of Chemistry. 16 (9) 105039. doi:10.1016/j.arabjc.2023.105039.
  8. ↑ "Obwieszczenie Ministra Zdrowia" (in Polish). eli.gov.pl. Archived from the original on 2026-10-12. Retrieved 2026-10-31.