Para-Chlorophenethylamine

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ATC code
  • none
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.

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

See also

References

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