3,4-Dichloroamphetamine

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3,4-Dichloroamphetamine
34DCA structure.png
Systematic (IUPAC) name
1-(3,4-dichlorophenyl)propan-2-amine
Identifiers
CAS Number 4806-87-5 N
ATC code none
PubChem CID: 17535
ChemSpider 16580 YesY
ChEMBL CHEMBL48888 YesY
Chemical data
Formula C9H11Cl2N
Molecular mass 204.096 g/mol
  • Clc1ccc(CC(N)C)cc1Cl
  • InChI=1S/C9H11Cl2N/c1-6(12)4-7-2-3-8(10)9(11)5-7/h2-3,5-6H,4,12H2,1H3 YesY
  • Key:PUFDZMUCDFIRQY-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

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][9]

See also

References

  1. ↑ Rodríguez GJ, Roman DL, White KJ, Nichols DE, Barker EL. Distinct recognition of substrates by the human and Drosophila serotonin transporters. Journal of Pharmacology and Experimental Therapeutics. 2003 Jul;306(1):338-46. PMID 12682215
  2. ↑ Roman DL, Saldaña SN, Nichols DE, Carroll FI, Barker EL. Distinct Molecular Recognition of Psychostimulants by Human and Drosophila Serotonin Transporters. Journal of Pharmacology and Experimental Therapeutics. 2004 Feb;308(2):679-87. PMID 14593087
  3. ↑ Walline CC, Nichols DE, Carroll FI, Barker EL. Comparative molecular field analysis using selectivity fields reveals residues in the third transmembrane helix of the serotonin transporter associated with substrate and antagonist recognition. Journal of Pharmacology and Experimental Therapeutics. 2008 Jun;325(3):791-800. PMID 18354055
  4. ↑ Wenthur CJ, Rodríguez GJ, Kuntz CP, Barker EL. Conformational flexibility of transmembrane helix VII of the human serotonin transporter impacts ion dependence and transport. Biochemical Pharmacology. 2010 Nov 1;80(9):1418-26. PMID 20637736
  5. ↑ Fuller RW, Hines CW, Mills J. Lowering of brain serotonin level by chloramphetamines. Biochemical Pharmacology. 1965 Apr;14:483-8. PMID 14322972
  6. ↑ Fuller RW, Walters CP. Inhibition of monoamine oxidase action on kynuramine by substrate amines and stereoisomeric α-methyl amines. Biochemical Pharmacology. 1965 Feb;14:159-63. PMID 14332461
  7. ↑ Fuller RW, Mills J, Marsh MM. Inhibition of phenethanolamine N-methyl transferase by ring-substituted alpha-methylphenethylamines (amphetamines). Journal of Medicinal Chemistry. 1971 Apr;14(4):322-5. PMID 5553744
  8. ↑ Fuller RW, Roush BW, Molloy BB. Regulation of phenylethanolamine N-methyl transferase. Advances in Enzyme Regulation. Volume 12, 1974, Pages 311-341. DOI 10.1016/0065-2571(74)90019-3
  9. ↑ Wu Q, Gee CL, Lin F, Tyndall JD, Martin JL, Grunewald GL, McLeish MJ. Structural, mutagenic, and kinetic analysis of the binding of substrates and inhibitors of human phenylethanolamine N-methyltransferase. Journal of Medicinal Chemistry. 2005 Nov 17;48(23):7243-52. PMID 16279783


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