Chemistry:3,4-Dichloroamphetamine
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| Formula | C9H11Cl2N |
| Molar mass | 204.09 g·mol−1 |
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3,4-Dichloroamphetamine (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, 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]
Synthesis
The reaction of 3,4-Dichlorobenzyl Chloride [102-47-6] (1) with cyanide anion gives 3,4-Dichlorophenylacetonitrile [3218-49-3] (2). Reaction with sodium methoxide and ethylacetate gives Alpha-Acetoxy-3,4-Dichlorobenzeneacetonitrile, CID:14318103 (3). Removal of the nitrile group in the presence of sulfuric acid gives 3,4-Dichlorophenylacetone [6097-32-1] (4). Oxime formation with hydroxylamine gives N-[1-(3,4-dichlorophenyl)propan-2-ylidene]hydroxylamine, CID:74315855 (5). Reduction of the oxime completed the synthesis of 3,4-Dichloroamphetamine (6).
See also
- 3-Methoxy-4-methylamphetamine
- Cericlamine
- Chlorphentermine
- Clortermine
- Etolorex
- 3,4-Methylenedioxyamphetamine
- Parachloroamphetamine
- Paramethoxyamphetamine
References
- ↑ "Distinct recognition of substrates by the human and Drosophila serotonin transporters". The Journal of Pharmacology and Experimental Therapeutics 306 (1): 338–46. July 2003. doi:10.1124/jpet.103.048751. PMID 12682215.
- ↑ "Distinct molecular recognition of psychostimulants by human and Drosophila serotonin transporters". The Journal of Pharmacology and Experimental Therapeutics 308 (2): 679–87. February 2004. doi:10.1124/jpet.103.057836. PMID 14593087.
- ↑ "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 325 (3): 791–800. June 2008. doi:10.1124/jpet.108.136200. PMID 18354055.
- ↑ "Conformational flexibility of transmembrane helix VII of the human serotonin transporter impacts ion dependence and transport". Biochemical Pharmacology 80 (9): 1418–26. November 2010. doi:10.1016/j.bcp.2010.07.005. PMID 20637736.
- ↑ "Lowering of brain serotonin level by chloramphetamines". Biochemical Pharmacology 14 (4): 483–8. April 1965. doi:10.1016/0006-2952(65)90221-2. PMID 14322972.
- ↑ "Inhibition of monoamine oxidase action on kynuramine by substrate amines and stereoisomeric α-methyl amines". Biochemical Pharmacology 14 (2): 159–63. February 1965. doi:10.1016/0006-2952(65)90071-7. PMID 14332461.
- ↑ "Inhibition of phenethanolamine N-methyl transferase by ring-substituted alpha-methylphenethylamines (amphetamines)". Journal of Medicinal Chemistry 14 (4): 322–5. April 1971. doi:10.1021/jm00286a012. PMID 5553744.
- ↑ "Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase". Journal of Medicinal Chemistry 48 (23): 7243–52. November 2005. doi:10.1021/jm050568o. PMID 16279783.
- ↑ Harley M Hanson, U.S. Patent 3,215,598 (1965 to Merck and Co Inc).
- ↑ Charles Jackson Barnett, U.S. Patent 4,199,525 (1980 to Eli Lilly and Co).
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