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| Other names | 3-CA;meta-Chloroamphetamine;m-Chloroamphetamine; MCA; PAL-304; PAL304 |
| Drug class | Psychostimulant;Serotonergic neurotoxin |
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| Chemical and physical data | |
| Formula | C9H12ClN |
| Molar mass | 169.65 g·mol−1 |
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3-Chloroamphetamine (3-CA; code namePAL-304), also known asmeta-chloroamphetamine (MCA), is apsychostimulant of theamphetamine family and aserotonergic neurotoxin related topara-chloroamphetamine (PCA; 4-chloroamphetamine).[1][2][3][4]
The drug is apotentserotonin–norepinephrine–dopamine releasing agent (SNDRA).[5][6][7] ItsEC50Tooltip half-maximal effective concentration values for induction ofmonoamine release are 9.4 nM fornorepinephrine, 11.8 nM fordopamine, and 120 nM forserotonin. Hence, 3-CA shows around 10-fold preference for induction ofcatecholamine release over induction of serotonin release.[5][6][8][9]
3-CA is closely related to thepotent 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 rapidmetabolism viapara-hydroxylation.[11][1] When the metabolism of 3-CA wasinhibited, the drug produced approximately equivalentserotonergic neurotoxicity to PCA.[11][1]
The position of the chloro substituent also markedly affects the activity of the compounds (Table 6). The effect of the meta derivative was approximately equivalent to that of the para derivative but only after inhibition of para-hydroxylation, while the ortho-substituted compound actually slightly raised rather than lowered the serotonin levels (Fuller and Molloy, 1974).
[...] was less potent than amphetamine, 3-chloroamphetamine and 4-chloroamphetamine in inducing motor stimulation [31]. [...]
[...] 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.
