Norfentanyl

Norfentanyl is an inactive synthetic opioid analgesic drug precursor.^[2] It is an analog and metabolite of fentanyl with the removal of the phenethyl moiety (or functional group) from fentanyl chemical structure.^{[3][4][5][6][7][8][9][10]}

Norfentanyl

Legal status
Legal status	BR: Class D1 (Drug precursors)[1]
Identifiers
IUPAC name N-phenyl-N-piperidin-4-ylpropanamide
CAS Number	1609-66-1
PubChem CID	259381
ChemSpider	227671 N
UNII	2MK6D8JV6J
ChEBI	CHEBI:62685
ChEMBL	ChEMBL3560524
CompTox Dashboard (EPA)	DTXSID2057657
ECHA InfoCard	100.015.040
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(=O)N(C1CCNCC1)C2=CC=CC=C2
InChI InChI=1S/C14H20N2O/c1-2-14(17)16(12-6-4-3-5-7-12)13-8-10-15-11-9-13/h3-7,13,15H,2,8-11H2,1H3 Key:PMCBDBWCQQBSRJ-UHFFFAOYSA-N

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

• 3-Methylbutyrfentanyl
• 4-Fluorobutyrfentanyl
• 4-Fluorofentanyl
• α-Methylfentanyl
• Acetylfentanyl
• Benzylfentanyl
• Furanylfentanyl
• Homofentanyl
• List of fentanyl analogues

References

1. Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
2. "Fentanyl". Elsevier.
3. 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.
4. 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.
5. Huynh, N-H.; et al. (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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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

• Higashikawa Y, Suzuki S (June 2008). "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. doi:10.1007/s11419-007-0039-1. S2CID 22092512.
• Alburges ME, Hanson GR, Gibb JW, Sakashita CO, Rollins DE (1992). "Fentanyl receptor assay. II. Utilization of a radioreceptor assay for the analysis of fentanyl analogs in urine". J Anal Toxicol. 16 (1): 36–41. doi:10.1093/jat/16.1.36. PMID 1322477.
• Woods J, Medzihradsky F, Smith C, Winger G, Gmerek D (1988). "Evaluation of new compounds for opioid activity: 1987 annual report". NIDA Res. Monogr. 81: 543–90. PMID 3136388.
• Aceto M, Bowman E, Harris L, May E (1988). "Dependence studies of new compounds in the rhesus monkey, rat, and mouse, 1987". NIDA Res. Monogr. 81: 485–542. PMID 3136386.
• Brine GA, Boldt KG, Huang PT, Sawyer DK, Carroll FI (2009). "Carbon-13 nuclear magnetic resonance spectra of fentanyl analogs". Journal of Heterocyclic Chemistry. 26 (3): 677–686. doi:10.1002/jhet.5570260329.