Chemistry:Norfentanyl

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Short description: Synthetic opioid analgesic metabolite and precursor
Norfentanyl
Norfentanyl.svg
Norfentanyl 3D BS.png
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)

Norfentanyl is an inactive synthetic opioid analgesic drug precursor.[1] It is an analog and metabolite of fentanyl with the removal of the phenethyl moiety (or functional group) from fentanyl chemical structure.[2][3][4][5][6][7][8][9]

Occurrence and Applications

Norfentanyl occurs primarily as a metabolite of its parent drug, fentanyl. However, it can also be used to synthesize fentanyl itself.

See also

References

  1. "Fentanyl". Elsevier. https://www.sciencedirect.com/topics/neuroscience/fentanyl. 
  2. Sofalvi, Szabolcs (2017). "An LC–MS-MS method for the analysis of carfentanil, 3-methylfentanyl, 2-furanyl fentanyl, acetyl fentanyl, fentanyl and norfentanyl in postmortem and impaired-driving cases". Journal of Analytical Toxicology 41 (6): 473–483. doi:10.1093/jat/bkx052. PMID 28830122. 
  3. Bista, Sudeep R. (2014). "Development, validation and application of an HPLC–MS/MS method for the determination of fentanyl and nor-fentanyl in human plasma and saliva.". Journal of Chromatography B (960): 27-33. 
  4. Huynh, N-H. (2005). "Determination of fentanyl in human plasma and fentanyl and norfentanyl in human urine using LC–MS/MS". Journal of Pharmaceutical and Biomedical Analysis 37 (5): 1095–1100. doi:10.1016/j.jpba.2004.09.024. PMID 15862690. 
  5. Poklis, Alphonse (2004). "Urine concentrations of fentanyl and norfentanyl during application of Duragesic® transdermal patches". Journal of Analytical Toxicology 28 (6): 422–425. doi:10.1093/jat/28.6.422. PMID 15516290. 
  6. Coopman, Vera (2007). "LC–MS/MS analysis of fentanyl and norfentanyl in a fatality due to application of multiple Durogesic® transdermal therapeutic systems". Forensic Science International 169 (2–3): 223–227. doi:10.1016/j.forsciint.2006.03.018. PMID 16650707. 
  7. Peer, Cody J. (2007). "Direct-injection mass spectrometric method for the rapid identification of fentanyl and norfentanyl in postmortem urine of six drug-overdose cases". Journal of Analytical Toxicology 31 (8): 515–521. doi:10.1093/jat/31.8.515. PMID 17988466. 
  8. Vandergrift, Gregory W. (2018). "Paper spray mass spectrometry for the direct, semi-quantitative measurement of fentanyl and norfentanyl in complex matrices". Clinical Biochemistry 54: 106–111. doi:10.1016/j.clinbiochem.2018.02.005. PMID 29432758. 
  9. Patton, Amy L. (2014). "Quantitative measurement of acetyl fentanyl and acetyl norfentanyl in human urine by LC-MS/MS". Analytical Chemistry 86 (3): 1760–1766. doi:10.1021/ac4036197. PMID 24354295. 

Further reading

  • "Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues". Forensic Toxicology 26 (1): 1–5. June 2008. doi:10.1007/s11419-007-0039-1. 
  • "Fentanyl receptor assay. II. Utilization of a radioreceptor assay for the analysis of fentanyl analogs in urine". J Anal Toxicol 16 (1): 36–41. 1992. doi:10.1093/jat/16.1.36. PMID 1322477. 
  • "Evaluation of new compounds for opioid activity: 1987 annual report". NIDA Res. Monogr. 81: 543–90. 1988. PMID 3136388. 
  • "Dependence studies of new compounds in the rhesus monkey, rat, and mouse, 1987". NIDA Res. Monogr. 81: 485–542. 1988. PMID 3136386. 
  • "Carbon-13 nuclear magnetic resonance spectra of fentanyl analogs". Journal of Heterocyclic Chemistry 26 (3): 677–686. 2009. doi:10.1002/jhet.5570260329.