3-Methylfentanyl

3-Methylfentanyl
Clinical data
Other names	3-methylfentanyl, Mefentanyl
Legal status
Legal status	AU: Unscheduled; BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); NZ: Unscheduled; UK: Class A; US: Schedule I; UN: Unscheduled;
Identifiers
	IUPAC name (RS)-N-(3-methyl-1-phenethyl-4-piperidyl)-N-phenyl-propanamide;
CAS Number	42045-86-3 ;
PubChem CID	61996;
DrugBank	DB01571 ;
ChemSpider	55844 ;
UNII	QVU94XE61A;
KEGG	C22793 ;
ChEBI	CHEBI:61092 ;
CompTox Dashboard (EPA)	DTXSID30962228 ;
Chemical and physical data
Formula	C23H30N2O
Molar mass	350.506 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CCC(=O)N(c1ccccc1)C2CCN(CC2C)CCc3ccccc3;
	InChI InChI=1S/C23H30N2O/c1-3-23(26)25(21-12-8-5-9-13-21)22-15-17-24(18-19(22)2)16-14-20-10-6-4-7-11-20/h4-13,19,22H,3,14-18H2,1-2H3 ; Key:MLQRZXNZHAOCHQ-UHFFFAOYSA-N ;
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3-Methylfentanyl (3-MF, mefentanyl) is an opioid analgesic that is an analog of fentanyl. 3-Methylfentanyl is one of the most potent opioids, estimated to be between 400 and 6000 times stronger than morphine,^[1] depending on which isomer is used (with the cis isomers being the more potent ones).^[2]^[3]

^ Henderson GL. Designer Drugs: Past History and Future Prospects Journal of Forensic Sciences. 33(2): 569-575 (1988)
^ Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, et al. (May 1981). "Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives". Scientia Sinica. 24 (5): 710–20. PMID 6264594.
^ Wang ZX, Zhu YC, Chen XJ, Ji RY (1993). "[Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity]". Yao Xue Xue Bao = Acta Pharmaceutica Sinica. 28 (12): 905–10. PMID 8030414.

[1] Henderson GL. Designer Drugs: Past History and Future Prospects Journal of Forensic Sciences. 33(2): 569-575 (1988)

[2] Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, et al. (May 1981). "Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives". Scientia Sinica. 24 (5): 710–20. PMID 6264594.

[3] Wang ZX, Zhu YC, Chen XJ, Ji RY (1993). "[Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity]". Yao Xue Xue Bao = Acta Pharmaceutica Sinica. 28 (12): 905–10. PMID 8030414.

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