3-Methylbutyrfentanyl

3-Methylbutyrfentanyl
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class A; US: Schedule I;
Identifiers
	IUPAC name N-[3-Methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylbutanamide;
CAS Number	97605-09-9;
PubChem CID	86130531;
ChemSpider	57434313;
UNII	875L53T89N;
CompTox Dashboard (EPA)	DTXSID501017180 ;
Chemical and physical data
Formula	C24H32N2O
Molar mass	364.533 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(=O)N(c1ccccc1)C2CCN(CC2C)CCc3ccccc3;
	InChI InChI=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; Key:ZPAOSKLOFZWBLS-UHFFFAOYSA-N;

3-Methylbutyrfentanyl (3-MBF) is an opioid analgesic that is an analog of butyrfentanyl.^[2]^[3]^[4]^[5]

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.^[6]

References

^ Drug Enforcement Administration, Department of Justice (2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.
^ Yoshiyasu Higashikawa; Shinichi Suzuki (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 (5): 1–5. doi:10.1007/s11419-007-0039-1.
^ Ruben S. Vardanyan; Victor J. Hruby (August 2014). "Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications". Future Medicinal Chemistry. 6 (4): 385–412. doi:10.4155/fmc.13.215. PMC 4137794. PMID 24635521.
^ Jin, W. Q.; Xu, H.; Zhu, Y. C.; Fang, S. N.; Xia, X. L.; Huang, Z. M.; Ge, B. L.; Chi, Z. Q. (1981). "Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives". Scientia Sinica. 24 (5): 710–720. PMID 6264594.
^ Huang, Z. M.; Zhou, J.; Chen, X. J.; Zheng, W. J.; Zhang, H. P.; Chi, Z. Q.; Li, Z. G.; Chen, W. L. (1984). "Analgesic activity and toxicity of potent analgesics, ohmefentanyl and mefentanyl". Zhongguo Yao Li Xue Bao. 5 (3): 153–158. PMID 6239505.
^ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.

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[1] Drug Enforcement Administration, Department of Justice (2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.

[2] Yoshiyasu Higashikawa; Shinichi Suzuki (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 (5): 1–5. doi:10.1007/s11419-007-0039-1.

[3] Ruben S. Vardanyan; Victor J. Hruby (August 2014). "Fentanyl-related compounds and derivatives: current status and future prospects for pharmaceutical applications". Future Medicinal Chemistry. 6 (4): 385–412. doi:10.4155/fmc.13.215. PMC 4137794. PMID 24635521.

[4] Jin, W. Q.; Xu, H.; Zhu, Y. C.; Fang, S. N.; Xia, X. L.; Huang, Z. M.; Ge, B. L.; Chi, Z. Q. (1981). "Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives". Scientia Sinica. 24 (5): 710–720. PMID 6264594.

[5] Huang, Z. M.; Zhou, J.; Chen, X. J.; Zheng, W. J.; Zhang, H. P.; Chi, Z. Q.; Li, Z. G.; Chen, W. L. (1984). "Analgesic activity and toxicity of potent analgesics, ohmefentanyl and mefentanyl". Zhongguo Yao Li Xue Bao. 5 (3): 153–158. PMID 6239505.

[6] Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.

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See also

References