Crotonylfentanyl

{{Short description|Opioid analgesic designer drug}}

{{Drugbox

| IUPAC_name = (2E)-N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-2-butenamide

| image = Crotonylfentanyl Structure.svg

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 760930-59-4

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

| UNII = R0XLG8CO63

| ATC_prefix =

| ATC_suffix =

| PubChem = 10472960

| KEGG = C22759

| DrugBank =

| ChemSpiderID = 8648371

| C=23 | H=28 | N=2 | O=1

| molecular_weight =

| smiles = O=C(/C=C/C)N(c1ccccc1)C3CCN(CCc2ccccc2)CC3

| StdInChI2 = 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+

| StdInChIKey2 = VDYXGPCGBKLRDA-XNWCZRBMBF

| StdInChI = 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+

| StdInChIKey = VDYXGPCGBKLRDA-XNWCZRBMSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category=

| legal_AU =

| legal_BR = F1

| legal_CA = Schedule I

| legal_DE = Anlage II

| legal_UK = Class A

| legal_UN = N I

| legal_US =

| legal_status =

| routes_of_administration =

}}

Crotonylfentanyl is an opioid analgesic that is an analog of fentanyl and structural isomer of cyclopropylfentanyl{{cite journal | vauthors = Mallette JR, Casale JF, Hays PA | title = Characterization and differentiation of cyclopropylfentanyl from E-crotonylfentanyl, Z-crotonylfentanyl, and 3-butenylfentanyl | journal = Science & Justice | volume = 59 | issue = 1 | pages = 67–74 | date = January 2019 | pmid = 30654970 | doi = 10.1016/j.scijus.2018.07.005 | s2cid = 58646707 }} and has been sold online as a designer drug.{{cite journal | vauthors = Varshneya NB, Walentiny DM, Moisa LT, Walker TD, Akinfiresoye LR, Beardsley PM | title = Opioid-like antinociceptive and locomotor effects of emerging fentanyl-related substances | journal = Neuropharmacology | volume = 151 | pages = 171–179 | date = June 2019 | pmid = 30904478 | pmc = 8992608 | doi = 10.1016/j.neuropharm.2019.03.023 | s2cid = 84182661 }}{{cite journal | vauthors = Palaty J, Konforte D, Karakosta T, Wong E, Stefan C | title = Rapid identification of cyclopropyl fentanyl/crotonyl fentanyl in clinical urine specimens: A case study of clinical laboratory collaboration in Canada | journal = Clinical Biochemistry | volume = 53 | pages = 164–167 | date = March 2018 | pmid = 29395089 | doi = 10.1016/j.clinbiochem.2018.01.013 }} In December 2019, the UNODC announced scheduling recommendations placing crotonylfentanyl into Schedule I.{{cite web|url=https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3|date = December 2019 | publisher = WHO | title = World Health Organization recommends 12 NPS for scheduling}}