Structure via PubChem · Public domain (PubChem)
p-chloroamphetamine
Sign in to saveAlso known as para-chloroamphetamine, 4-chloroamphetamine, parachloroamphetamine
'''para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA'''), is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonergic neurotoxin of the amphetamine family. It is used in scientific research in the study of the serotonin system, as a serotonin releasing agent (SRA) at lower doses to produce serotonergic effects, and as a serotonergic neurotoxin at higher doses to produce long-lasting depletions of serotonin.
Chemical data
- Formula
- C9H12ClN
- Molecular weight
- 169.65 g/mol
- IUPAC name
- 1-(4-chlorophenyl)propan-2-amine
- SMILES
- CC(CC1=CC=C(C=C1)Cl)N
- InChIKey
- WWPITPSIWMXDPE-UHFFFAOYSA-N
- XLogP
- 2.4
- Polar surface area
- 26 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
865 papers- p-Chloroamphetamine decreases serotonin and induces apoptosis in granulosa cells and follicular atresia in prepubertal female rats.Reproductive toxicology (Elmsford, N.Y.) · 2022
- Effects of p-chloroamphetamine on brain serotonin neurons.Neurochemical research · 1992
- p-Chloroamphetamine-Enhanced Neostriatal Dopamine Exocytosis in Rats Neonatally Co-lesioned with 6-OHDA and 5,7-DHT: Relevance to Parkinson's Disease.Neurotoxicity research · 2020
- p-Chloroamphetamine antagonism of cobaltous chloride-induced hypothermia in mice.European journal of pharmacology · 1979
- p-Chloroamphetamine induces serotonin release through serotonin transporters.Biochemistry · 1992
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 169.065827
Show 4 more facts
- canonical SMILES
- CC(CC1=CC=C(C=C1)Cl)N
- chemical formula
- C₉H₁₂ClN
- subject has role
- serotonergic agent
- Commons category
- 4-Chloroamphetamine
via Wikidata · CC0
~17 min read
Encyclopedic overview
16 sectionsContents
- Effects
- Pharmacology
- Monoamine releasing agent
- Short-term effects
- Long-term serotonergic neurotoxicity
- Mechanisms of neurotoxicity
- Structure–activity relationships of neurotoxicity
- Use as a neurotoxin in scientific research
- Other actions
- Chemistry
- History
- Society and culture
- Legal status
- China
- United States
- References
'''para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA'), is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonergic neurotoxin of the amphetamine family. It is used in scientific research in the study of the serotonin system, as a serotonin releasing agent (SRA) at lower doses to produce serotonergic effects, and as a serotonergic neurotoxin at higher doses to produce long-lasting depletions of serotonin.
PCA has also been clinically studied as an appetite suppressant and antidepressant, but findings of neurotoxicity in animals discouraged further evaluation. It has also been encountered as a designer drug, although it never achieved popularity, again perhaps due to its neurotoxicity.
Excerpted from Wikipedia’s “p-chloroamphetamine” article, available under the CC BY-SA 4.0 licence.