3-Chloroamphetamine

3-Chloroamphetamine

Clinical data
Other names	3-CA; meta-Chloroamphetamine; m-Chloroamphetamine
Drug class	Psychostimulant; Serotonergic neurotoxin
Identifiers
IUPAC name 1-(3-chlorophenyl)propan-2-amine
CAS Number	32560-59-1
PubChem CID	20027470
ChemSpider	14677942
UNII	8V8DE89CJE
ChEMBL	ChEMBL149022
Chemical and physical data
Formula	C9H12ClN
Molar mass	169.65 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC(=CC=C1)Cl)N
InChI InChI=1S/C9H12ClN/c1-7(11)5-8-3-2-4-9(10)6-8/h2-4,6-7H,5,11H2,1H3 Key:ORWQJKNRYUIFJU-UHFFFAOYSA-N

3-Chloroamphetamine (3-CA), also known as meta-chloroamphetamine, is a psychostimulant of the amphetamine family and a potent serotonergic neurotoxin related to para-chloroamphetamine (PCA).^[1][2][3][4]

See also

• 2,4-Dichloroamphetamine (2,4-DCA)
• 3,4-Dichloroamphetamine (3,4-DCA)
• 3-Chloromethamphetamine
• 3-Chloromethcathinone

References

1. Biel JH, Bopp BA (1978). "Amphetamines: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. p. 1–39. doi:10.1007/978-1-4757-0510-2_1. ISBN 978-1-4757-0512-6.
2. Coppola M, Mondola R (December 2013). "4-methylamphetamine (4-MA): chemistry, pharmacology and toxicology of a new potential recreational drug". Mini Reviews in Medicinal Chemistry. 13 (14): 2097–2101. doi:10.2174/13895575113136660106. PMID 24195663. [...] was less potent than amphetamine, 3-chloroamphetamine and 4-chloroamphetamine in inducing motor stimulation [31]. [...]
3. Lapoint J, Welker KL (2022). "Synthetic amphetamine derivatives, benzofurans, and benzodifurans". In Dargan P, Wood D (eds.). Novel Psychoactive Substances. Elsevier. pp. 247–278. doi:10.1016/b978-0-12-818788-3.00007-3. ISBN 978-0-12-818788-3. [...] amphetamine analogue required to increase motor activity by 200 percent was 38 μmol/kg for 4-MA, 16 μmol/kg for amphetamine and 24 μmol/kg for both 2- and 3-chloroamphetamine.
4. Fuller RW, Baker JC (November 1974). "Long-lasting reduction of brain 5-hydroxytryptamine concentration by 3-chloramphetamine and 4-chloroamphetamine in iprindole-treated rats". The Journal of Pharmacy and Pharmacology. 26 (11): 912–914. doi:10.1111/j.2042-7158.1974.tb09206.x. PMID 4156568.