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3,4-Dichloroamphetamine

Chemical compound

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3,4-Dichloroamphetamine (3,4-DCA), 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 (SSRA) 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 (PCA), though with slightly lower potency. It is also a monoamine oxidase inhibitor (MAOI), 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

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The reaction of 3,4-dichlorobenzyl chloride (1) with cyanide anion gives 3,4-dichlorophenylacetonitrile (2). Reaction with sodium methoxide and ethyl acetate gives α-acetoxy-3,4-dichlorophenylacetonitrile, (3). Removal of the nitrile group in the presence of sulfuric acid gives 3,4-dichlorophenylacetone (4). Oxime formation with hydroxylamine gives N-[1-(3,4-dichlorophenyl)propan-2-ylidene]hydroxylamine, (5). Reduction of the oxime completed the synthesis of 3,4-dichloroamphetamine (6).

For the supposedly non-neurotoxic 5,6-DCAT & 6,7-DCAT see under 6-CAT.

References

(July 2003). "Distinct recognition of substrates by the human and Drosophila serotonin transporters". The Journal of Pharmacology and Experimental Therapeutics.
(February 2004). "Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters". The Journal of Pharmacology and Experimental Therapeutics.
(June 2008). "Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition". The Journal of Pharmacology and Experimental Therapeutics.
(November 2010). "Conformational flexibility of transmembrane helix VII of the human serotonin transporter impacts ion dependence and transport". Biochemical Pharmacology.
(April 1965). "Lowering of brain serotonin level by chloramphetamines". Biochemical Pharmacology.
(February 1965). "Inhibition of monoamine oxidase action on kynuramine by substrate amines and stereoisomeric α-methyl amines". Biochemical Pharmacology.
(April 1971). "Inhibition of phenethanolamine N-methyl transferase by ring-substituted alpha-methylphenethylamines (amphetamines)". Journal of Medicinal Chemistry.
(November 2005). "Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase". Journal of Medicinal Chemistry.
Harley M Hanson, {{US patent. 3215598 (1965 to Merck and Co Inc).
Charles Jackson Barnett, {{US patent. 4199525 (1980 to Eli Lilly and Co).

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abandoned-drugs monoamine-oxidase-inhibitors monoaminergic-neurotoxins serotonin-norepinephrine-dopamine-releasing-agents serotonin-releasing-agents substituted-amphetamines

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