Norfentanyl

{{Short description|Synthetic opioid analgesic metabolite and precursor}}

{{Use dmy dates|date=July 2022}}

{{Drugbox

| verifiedrevid =

| IUPAC_name = N-phenyl-N-piperidin-4-ylpropanamide

| image = Norfentanyl.svg

| width = 220px

| image2 = Norfentanyl 3D BS.png

| width2 = 220px

| tradename =

| legal_BR = D1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_DE =

| legal_UK =

| legal_US =

| CAS_number = 1609-66-1

| PubChem = 259381

| ATC_prefix =

| ChEBI = 62685

| ChEMBL = 3560524

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 227671

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2MK6D8JV6J

| C=14 | H=20 | N=2 | O=1

| smiles = CCC(=O)N(C1CCNCC1)C2=CC=CC=C2

| StdInChI = 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

| StdInChIKey = PMCBDBWCQQBSRJ-UHFFFAOYSA-N

}}

Norfentanyl is an inactive synthetic opioid analgesic drug precursor.{{Cite web |title=Fentanyl |url=https://www.sciencedirect.com/topics/neuroscience/fentanyl |publisher=Elsevier}} It is an analog and metabolite of fentanyl with the removal of the phenethyl moiety (or functional group) from fentanyl chemical structure.{{cite journal |last1=Sofalvi |first1=Szabolcs |title=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=Journal of Analytical Toxicology |date=2017 |volume=41 |issue=6 |pages=473–483 |doi=10.1093/jat/bkx052 |pmid=28830122 |doi-access=free }}{{cite journal |last1=Bista |first1=Sudeep R. |title=Development, validation and application of an HPLC–MS/MS method for the determination of fentanyl and nor-fentanyl in human plasma and saliva. |journal=Journal of Chromatography |date=2014 |volume=B |issue=960 |page=27-33}}{{cite journal |last1=Huynh |first1=N-H. |display-authors=etal |title=Determination of fentanyl in human plasma and fentanyl and norfentanyl in human urine using LC–MS/MS |journal=Journal of Pharmaceutical and Biomedical Analysis |date=2005 |volume=37 |issue=5 |pages=1095–1100 |doi=10.1016/j.jpba.2004.09.024 |pmid=15862690 }}{{cite journal |last1=Poklis |first1=Alphonse |title=Urine concentrations of fentanyl and norfentanyl during application of Duragesic® transdermal patches |journal=Journal of Analytical Toxicology |date=2004 |volume=28 |issue=6 |pages=422–425 |doi=10.1093/jat/28.6.422 |pmid=15516290 |doi-access=free }}{{cite journal |last1=Coopman |first1=Vera |title=LC–MS/MS analysis of fentanyl and norfentanyl in a fatality due to application of multiple Durogesic® transdermal therapeutic systems |journal=Forensic Science International |date=2007 |volume=169 |issue=2–3 |pages=223–227 |doi=10.1016/j.forsciint.2006.03.018 |pmid=16650707 }}{{cite journal |last1=Peer |first1=Cody J. |title=Direct-injection mass spectrometric method for the rapid identification of fentanyl and norfentanyl in postmortem urine of six drug-overdose cases |journal=Journal of Analytical Toxicology |date=2007 |volume=31 |issue=8 |pages=515–521 |doi=10.1093/jat/31.8.515 |pmid=17988466 |doi-access=free }}{{cite journal |last1=Vandergrift |first1=Gregory W. |title=Paper spray mass spectrometry for the direct, semi-quantitative measurement of fentanyl and norfentanyl in complex matrices |journal=Clinical Biochemistry |date=2018 |volume=54 |pages=106–111 |doi=10.1016/j.clinbiochem.2018.02.005 |pmid=29432758 }}{{cite journal |last1=Patton |first1=Amy L. |title=Quantitative measurement of acetyl fentanyl and acetyl norfentanyl in human urine by LC-MS/MS |journal=Analytical Chemistry |date=2014 |volume=86 |issue=3 |pages=1760–1766 |doi=10.1021/ac4036197 |pmid=24354295 }}