3,4-Dichloroamphetamine
Chemical compound
From Wikipedia, the free encyclopedia
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,[1][2][3][4] but also acts as a selective serotonergic neurotoxin in a similar manner to the related para-chloroamphetamine (PCA), though with slightly lower potency.[5] It is also a monoamine oxidase inhibitor (MAOI),[6] 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.[7][8]
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| Other names | 3,4-DCA |
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| ECHA InfoCard | 100.023.060 |
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| Formula | C9H11Cl2N |
| Molar mass | 204.09 g·mol−1 |
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Chemistry
Synthesis
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.