3,4-Dichloroamphetamine
3,4-Dichloroamphetamine, is an amphetamine derived drug invented by Eli Lilly in the 1960s, which has a number of pharmacological actions. It acts as a highly potent and selective serotonin releasing agent and binds to the serotonin transporter with high affinity, but also acts as a selective serotonergic neurotoxin in a similar manner to the related para-chloroamphetamine, though with slightly lower potency. It is also a monoamine oxidase inhibitor, as well as a very potent inhibitor of the enzyme phenylethanolamine N-methyl transferase which normally functions to transform noradrenaline into adrenaline in the body.
Chemistry
Synthesis
The reaction of 3,4-dichlorobenzyl chloride with cyanide anion gives 3,4-dichlorophenylacetonitrile. Reaction with sodium methoxide and ethyl acetate gives α-acetoxy-3,4-dichlorophenylacetonitrile,. Removal of the nitrile group in the presence of sulfuric acid gives 3,4-dichlorophenylacetone. Oxime formation with hydroxylamine gives N-hydroxylamine,. Reduction of the oxime completed the synthesis of 3,4-dichloroamphetamine.For the supposedly non-neurotoxic 5,6-DCAT & 6,7-DCAT see under 6-CAT.