Crotonylfentanyl

Crotonylfentanyl
Legal status
Legal status	BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; UN: Narcotic Schedule I;
Identifiers
	IUPAC name (2E)-N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-2-butenamide;
CAS Number	760930-59-4 ;
PubChem CID	10472960;
ChemSpider	8648371;
UNII	R0XLG8CO63;
KEGG	C22759;
Chemical and physical data
Formula	C23H28N2O
Molar mass	348.490 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(/C=C/C)N(c1ccccc1)C3CCN(CCc2ccccc2)CC3;
	InChI InChI=1S/C23H28N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h2-13,22H,14-19H2,1H3/b9-2+; Key:VDYXGPCGBKLRDA-XNWCZRBMSA-N; ; InChI=1/C23H28N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h2-13,22H,14-19H2,1H3/b9-2+; Key:VDYXGPCGBKLRDA-XNWCZRBMBF;

Crotonylfentanyl is an opioid analgesic that is an analog of fentanyl and structural isomer of cyclopropylfentanyl^[1] and has been sold online as a designer drug.^[2]^[3] In December 2019, the UNODC announced scheduling recommendations placing crotonylfentanyl into Schedule I.^[4]

References

^ Mallette JR, Casale JF, Hays PA (January 2019). "Characterization and differentiation of cyclopropylfentanyl from E-crotonylfentanyl, Z-crotonylfentanyl, and 3-butenylfentanyl". Science & Justice. 59 (1): 67–74. doi:10.1016/j.scijus.2018.07.005. PMID 30654970. S2CID 58646707.
^ Varshneya NB, Walentiny DM, Moisa LT, Walker TD, Akinfiresoye LR, Beardsley PM (June 2019). "Opioid-like antinociceptive and locomotor effects of emerging fentanyl-related substances". Neuropharmacology. 151: 171–179. doi:10.1016/j.neuropharm.2019.03.023. PMC 8992608. PMID 30904478. S2CID 84182661.
^ Palaty J, Konforte D, Karakosta T, Wong E, Stefan C (March 2018). "Rapid identification of cyclopropyl fentanyl/crotonyl fentanyl in clinical urine specimens: A case study of clinical laboratory collaboration in Canada". Clinical Biochemistry. 53: 164–167. doi:10.1016/j.clinbiochem.2018.01.013. PMID 29395089.
^ "World Health Organization recommends 12 NPS for scheduling". WHO. December 2019.

Legal status

Legal status	BR: Class F1 (Prohibited narcotics) CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Class A UN: Narcotic Schedule I
Identifiers
IUPAC name (2E)-N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-2-butenamide
CAS Number	760930-59-4^Y
PubChem CID	10472960
ChemSpider	8648371
UNII	R0XLG8CO63
KEGG	C22759
Chemical and physical data
Formula	C₂₃H₂₈N₂O
Molar mass	348.490 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(/C=C/C)N(c1ccccc1)C3CCN(CCc2ccccc2)CC3
InChI InChI=1S/C23H28N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h2-13,22H,14-19H2,1H3/b9-2+ Key:VDYXGPCGBKLRDA-XNWCZRBMSA-N InChI=1/C23H28N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h2-13,22H,14-19H2,1H3/b9-2+ Key:VDYXGPCGBKLRDA-XNWCZRBMBF