3-Chloroamphetamine

3-Chloroamphetamine
Clinical data
Other names	3-CA; meta-Chloroamphetamine; m-Chloroamphetamine; MCA; PAL-304; PAL304
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;
CompTox Dashboard (EPA)	DTXSID501043400 ;
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; code name PAL-304), also known as meta-chloroamphetamine (MCA), is a psychostimulant of the amphetamine family and a serotonergic neurotoxin related to para-chloroamphetamine (PCA; 4-chloroamphetamine).^[1]^[2]^[3]^[4]

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The drug is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).^[5]^[6]^[7] Its EC₅₀Tooltip half-maximal effective concentration values for induction of monoamine release are 9.4 nM for norepinephrine, 11.8 nM for dopamine, and 120 nM for serotonin. Hence, 3-CA shows around 10-fold preference for induction of catecholamine release over induction of serotonin release.^[5]^[6]^[8]^[9]

3-CA is closely related to the potent serotonergic neurotoxin PCA.^[10]^[11]^[1] In contrast to PCA, 3-CA produced no serotonergic neurotoxicity in rodents.^[10]^[11]^[1] However, this was found to be due to rapid metabolism via para-hydroxylation.^[11]^[1] When the metabolism of 3-CA was inhibited, the drug produced approximately equivalent serotonergic neurotoxicity to PCA.^[11]^[1]

See also