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4-Fluoropethidine: Difference between revisions

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Revision as of 22:05, 27 November 2012 editC6541 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers7,495 edits added Category:Dopamine reuptake inhibitors using HotCat← Previous edit Revision as of 12:06, 2 December 2012 edit undo213.106.56.145 (talk) Fixed SMILES to match imageNext edit →
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| C=15 | H=20 | F=1 | N=1 | O=2 | C=15 | H=20 | F=1 | N=1 | O=2
| molecular_weight = 265.322 g/mol | molecular_weight = 265.322 g/mol
| smiles = Fc2ccc(cc2)C(C(=O)OCC)(CC1)CCN1C | smiles = FC1=CC=C(C2(CCN(C)CC2)C(OCC)=O)C=C1
| InChI = 1/C15H20FNO2/c1-3-19-14(18)15(8-10-17(2)11-9-15)12-4-6-13(16)7-5-12/h4-7H,3,8-11H2,1-2H3 | InChI = 1/C15H20FNO2/c1-3-19-14(18)15(8-10-17(2)11-9-15)12-4-6-13(16)7-5-12/h4-7H,3,8-11H2,1-2H3
| InChIKey = CHOQGLPFQOQESN-UHFFFAOYAI | InChIKey = CHOQGLPFQOQESN-UHFFFAOYAI

Revision as of 12:06, 2 December 2012

Pharmaceutical compound
4-Fluoropethidine
Clinical data
Other names4-Fluoromeperidine, 4-Fluoropethidine
ATC code
  • none
Identifiers
IUPAC name
  • ethyl 4-(4-fluorophenyl)-1-methylpiperidine-4-carboxylate
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H20FNO2
Molar mass265.322 g/mol g·mol
3D model (JSmol)
SMILES
  • FC1=CC=C(C2(CCN(C)CC2)C(OCC)=O)C=C1
InChI
  • InChI=1S/C15H20FNO2/c1-3-19-14(18)15(8-10-17(2)11-9-15)12-4-6-13(16)7-5-12/h4-7H,3,8-11H2,1-2H3
  • Key:CHOQGLPFQOQESN-UHFFFAOYSA-N
  (verify)

4-Fluoropethidine is a drug that is a derivative of pethidine (meperidine), which combines pethidine's opioid analgesic effects with increased monoamine reuptake inhibition. It is around 50% less potent than pethidine as an opioid analgesic, but conversely is 50% more potent as a dopamine reuptake inhibitor, with other derivatives such as the 4-iodo and 3,4-dichloro analogues being even more potent dopamine reuptake inhibitors again. However none of these compounds substitute for cocaine or produce stimulant effects in animals, suggesting that they still act primarily as opioid analgesic drugs in practice.

See also

References

  1. Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML (2005). "Synthesis and biological evaluation of meperidine analogues at monoamine transporters". Journal of Medicinal Chemistry. 48 (5): 1336–43. doi:10.1021/jm0401614. PMID 15743177. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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