para-Chlorophenethylamine

para-Chlorophenethylamine
Clinical data
Drug classserotonergic agent; serotonin-releasing agent; monoaminergic neurotoxin
ATC code
  • none
Identifiers
  • 2-(4-chlorophenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC8H10ClN
Molar mass155.63 g·mol−1
3D model (JSmol)
  • C1=CC(=CC=C1CCN)Cl
  • InChI=1S/C8H10ClN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5-6,10H2
  • Key:SRXFXCKTIGELTI-UHFFFAOYSA-N

para-Chlorophenethylamine (pCPE) also known as 4-chlorophenylethylamine, is a potent serotonergic drug that is a structural analog of para-chloroamphetamine, lacking a methyl group at the α-position.

Pharmacology

Pharmacodynamics

para-Chlorophenethylamine acts primarily as a serotonin-releasing agent with an EC50Tooltip Half maximal effective concentration value of 430 nM for the serotonin transporter, approximately the dose required to induce serotonin syndrome with seizures, tremor, and hyperthermia in mice, is quite low compared to other derivatives (such as ortho-chlorophenethylamine and meta-chlorophenethylamine)[1][2] In mice with serotonin syndrome induced by para-chlorophenethylamine, the following symptoms were observed: lateral head bobbing, a Straub tail reaction, abduction of the hind limbs, tremors, hyperactivity, mutual pawing with the front paws, salivation, and piloerection.[3] It acts as a full, weak agonist of TAAR with an EC50 value of 2,900 ± 1,000 nM.[4]

In vitro, it inhibited the activity of the enzyme phenylethanolamine N-methyltransferase.[5] Para-chlorophenelethylamine stimulated 5-HT receptors.[3][6]

Pharmacokinetics

para-Chlorophenethylamine is a known metabolite of the para-chlorophenylalanine (fenclonine); it rapidly accumulated in the brain following administration of fenclonine.[7]

Drug control

Para-chlorophenylethylamine is a controlled substance in Hungary, classified under the category "New Psychoactive Substances"[8]

See also

References

  1. ^ Chung Hwang E, Van Woert MH (May 1980). "Comparative effects of substituted phenylethylamines on brain serotonergic mechanisms". The Journal of Pharmacology and Experimental Therapeutics. 213 (2): 254–260. doi:10.1016/S0022-3565(25)32053-7. PMID 6965983.
  2. ^ Hwang EC, Van Woert MH (December 1980). "Comparative effects of various serotonin releasing agents in mice". Biochemical Pharmacology. 29 (23): 3163–3167. doi:10.1016/0006-2952(80)90580-8. PMID 6449931.
  3. ^ a b Hwang EC, Van Woert MH (February 1979). "Behavioral and biochemical actions of p-chlorophenylethylamine (p-CPEA) in mice". Life Sciences. 24 (7): 595–601. doi:10.1016/0024-3205(79)90155-3. PMID 155767.
  4. ^ Lewin AH, Navarro HA, Mascarella SW (August 2008). "Structure-activity correlations for beta-phenethylamines at human trace amine receptor 1". Bioorganic & Medicinal Chemistry. 16 (15): 7415–7423. doi:10.1016/j.bmc.2008.06.009. PMC 2601700. PMID 18602830.
  5. ^ Coen CW, Coombs MC, Wilson PM, Clement EM, MacKinnon PC (March 1983). "Possible resolution of a paradox concerning the use of p-chlorophenylalanine and 5-hydroxytryptophan: evidence for a mode of action involving adrenaline in manipulating the surge of luteinizing hormone in rats". Neuroscience. 8 (3): 583–591. doi:10.1016/0306-4522(83)90200-2. PMID 6222267.
  6. ^ Sloviter RS, Connor JD, Damiano BP, Drust EG (August 1980). "Para-halogenated phenethylamines: similar serotonergic effects in rats by different mechanisms". Pharmacology, Biochemistry, and Behavior. 13 (2): 283–286. doi:10.1016/0091-3057(80)90084-2. PMID 6447879.
  7. ^ Baker GB, Martin IL, Coutts RT, Benderly A (1982). "Para-chlorophenylethylamine in brains of rats treated with a monoamine oxidase inhibitor and p-chlorophenylalanine". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 6 (4–6): 343–346. doi:10.1016/s0278-5846(82)80103-6. PMID 6219431.
  8. ^ "78/2022. (XII. 28.) BM rendelet - Nemzeti Jogszabálytár". njt.hu. Retrieved 2026-04-24.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.