3-Methylbutyrfentanyl

{{Short description|Opioid analgesic}}

{{Drugbox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| IUPAC_name = N-[3-Methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylbutanamide

| image = 3-Methylbutyrfentanyl_structure.png

| image_class = skin-invert-image

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| tradename =

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA = Schedule I

| legal_DE = NpSG

| legal_UK = Class A

| legal_US = Schedule I{{cite journal | author = Drug Enforcement Administration, Department of Justice | title = Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order | journal = Federal Register | volume = 83 | issue = 25 | pages = 5188–92 | date = February 2018 | pmid = 29932611 }}

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| CAS_number_Ref =

| CAS_number = 97605-09-9

| ATC_prefix =

| ATC_suffix =

| PubChem = 86130531

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID = 57434313

| ChEBI_Ref =

| ChEBI =

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

| UNII = 875L53T89N

| C=24 | H=32 | N=2 | O=1

| smiles = CCCC(=O)N(c1ccccc1)C2CCN(CC2C)CCc3ccccc3

| StdInChI_Ref =

| StdInChI = 1S/C24H32N2O/c1-3-10-24(27)26(22-13-8-5-9-14-22)23-16-18-25(19-20(23)2)17-15-21-11-6-4-7-12-21/h4-9,11-14,20,23H,3,10,15-19H2,1-2

| StdInChIKey_Ref =

| StdInChIKey = ZPAOSKLOFZWBLS-UHFFFAOYSA-N

| synonyms =

}}

3-Methylbutyrfentanyl (3-MBF) is an opioid analgesic that is an analog of butyrfentanyl.{{cite journal | vauthors = Higashikawa Y, Suzuki S | s2cid=22092512 | title=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 | journal=Forensic Toxicology |date=June 2008 | volume=26 | issue=5 | pages=1–5 | doi=10.1007/s11419-007-0039-1}}{{cite journal | vauthors = Vardanyan RS, Hruby VJ | title = Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications | journal = Future Medicinal Chemistry | volume = 6 | issue = 4 | pages = 385–412 | date = March 2014 | pmid = 24635521 | pmc = 4137794 | doi = 10.4155/fmc.13.215 }}{{cite journal | vauthors = Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, Ge BL, Chi ZQ | display-authors = 6 | title = Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives | journal = Scientia Sinica | volume = 24 | issue = 5 | pages = 710–20 | date = May 1981 | pmid = 6264594 }}{{cite journal | vauthors = Huang ZM, Zhou J, Chen XJ, Zheng WJ, Zhang HP, Chi ZQ, Li ZG, Chen WL | display-authors = 6 | title = [Analgesic activity and toxicity of potent analgesics, ohmefentanyl and mefentanyl] | journal = Zhongguo Yao Li Xue Bao = Acta Pharmacologica Sinica | volume = 5 | issue = 3 | pages = 153–8 | date = September 1984 | pmid = 6239505 }}

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.{{cite journal | vauthors = Mounteney J, Giraudon I, Denissov G, Griffiths P | title = Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe | journal = The International Journal on Drug Policy | volume = 26 | issue = 7 | pages = 626–31 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 | url = http://www.ijdp.org/article/S0955-3959%2815%2900097-3/abstract }}