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Revision as of 12:16, 20 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'CAS_number_Ref') per Chem/Drugbox validation (report errors o...← Previous edit Latest revision as of 09:35, 5 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Fluoroarenes; added Category:4-Fluorophenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Watchedfields = changed
| verifiedrevid = 456502672 | verifiedrevid = 477221845
| IUPAC_name = ethyl 4-(4-fluorophenyl)-1-methylpiperidine-4-carboxylate | IUPAC_name = ethyl 4-(4-fluorophenyl)-1-methylpiperidine-4-carboxylate
| image = 4-Fluoromeperidine.png | image = 4-Fluoropethidine Structure.svg
| width = 240 | width = 240


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<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = | CAS_number = 258500-87-7
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
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<!--Chemical data--> <!--Chemical data-->
| C=15 | H=20 | F=1 | N=1 | O=2 | C=15 | H=20 | F=1 | N=1 | O=2
| smiles = FC1=CC=C(C2(CCN(C)CC2)C(OCC)=O)C=C1
| molecular_weight = 265.322 g/mol
| smiles = Fc2ccc(cc2)C(C(=O)OCC)(CC1)CCN1C
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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}} }}


'''4-Fluoropethidine''' is a drug that is a derivative of ] (meperidine), which combines pethidine's ] ] effects with increased ] ]. It is around 50% less potent than pethidine as an opioid analgesic, but conversely is 50% more potent as a ], 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 ] or produce ] effects in animals, suggesting that they still act primarily as opioid analgesic drugs in practice.<ref name="pmid15743177">{{cite journal |author=Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML |title=Synthesis and biological evaluation of meperidine analogues at monoamine transporters |journal=Journal of Medicinal Chemistry |volume=48 |issue=5 |pages=1336–43 |year=2005 |month=March |pmid=15743177 |doi=10.1021/jm0401614 |url=}}</ref> '''4-Fluoropethidine''' is a drug that is a derivative of ] (meperidine), which combines pethidine's ] ] effects with increased ] ]. It is around 50% less potent than pethidine as an opioid analgesic, but conversely is 50% more potent as a ], 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 ] or produce ] effects in animals, suggesting that they still act primarily as opioid analgesic drugs in practice.<ref name="pmid15743177">{{cite journal |vauthors =Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML |title=Synthesis and biological evaluation of meperidine analogues at monoamine transporters |journal=Journal of Medicinal Chemistry |volume=48 |issue=5 |pages=1336–43 |date=March 2005 |pmid=15743177 |doi=10.1021/jm0401614 }}</ref> Its action and degree of relation to pethidine means that it may be controlled in those countries which have laws about controlled-substance analogues; it is not itself listed in the Controlled Substances Act 1970.<ref>{{Cite web|url=https://www.dea.gov/controlled-substances-act|title=The Controlled Substances Act}}</ref>


==See also== ==See also==
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== References == == References ==
{{reflist}} {{Reflist}}

{{Opioid receptor modulators}}
{{Monoamine reuptake inhibitors}}


{{DEFAULTSORT:Fluoromeperidine, 4-}} {{DEFAULTSORT:Fluoromeperidine, 4-}}

] ]
] ]
] ]
] ]
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{{analgesic-stub}} {{analgesic-stub}}

Latest revision as of 09:35, 5 September 2024

Chemical compound 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
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H20FNO2
Molar mass265.328 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. Its action and degree of relation to pethidine means that it may be controlled in those countries which have laws about controlled-substance analogues; it is not itself listed in the Controlled Substances Act 1970.

See also

References

  1. Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML (March 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.
  2. "The Controlled Substances Act".
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
Monoamine reuptake inhibitors
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins


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