3-Chloroamphetamine

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3-Chloroamphetamine
File:3-Chloroamphetamine.svg
Clinical data
Other names3-CA; meta-Chloroamphetamine; m-Chloroamphetamine; MCA; PAL-304; PAL304
Drug classPsychostimulant; Serotonergic neurotoxin
Identifiers
  • 1-(3-chlorophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC9H12ClN
Molar mass169.65 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=CC=C1)Cl)N
  • 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]

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

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References

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