Carfentanil

Carfentanil
Clinical data
Trade names	Wildnil
Other names	(4-Methoxycarbonyl)fentanyl, R-33799
AHFS/Drugs.com	International Drug Names
ATC code	None;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule II; In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	7.7 hours
Identifiers
	IUPAC name Methyl 1-(2-phenylethyl)-4-[phenyl(propanoyl)amino]piperidine-4-carboxylate;
CAS Number	59708-52-0 ;
PubChem CID	62156;
IUPHAR/BPS	10040;
DrugBank	DB01535 ;
ChemSpider	55986 ;
UNII	LA9DTA2L8F;
KEGG	D07620 ;
ChEBI	CHEBI:61084 ;
ChEMBL	ChEMBL290429 ;
CompTox Dashboard (EPA)	DTXSID40208427 ;
ECHA InfoCard	100.352.183
Chemical and physical data
Formula	C24H30N2O3
Molar mass	394.515 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)N(c1ccccc1)C2(C(=O)OC)CCN(CC2)CCc3ccccc3;
	InChI InChI=1S/C24H30N2O3/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20/h4-13H,3,14-19H2,1-2H3 ; Key:YDSDEBIZUNNPOB-UHFFFAOYSA-N ;
	(verify)

Carfentanil or carfentanyl, formerly sold under the brand name Wildnil, is an extremely potent opioid analgesic used in veterinary medicine to anesthetize large animals such as elephants and rhinoceroses.^[1] It is a structural analogue of the synthetic opioid analgesic fentanyl.^[2] It is typically administered in this context by tranquilizer dart.^[1] Carfentanil has also been used in humans to image opioid receptors.^[1] It has additionally been used as a recreational drug, typically by injection, insufflation, or inhalation.^[1] Deaths have been reported in association with carfentanil.^[1]^[3]

Effects and side effects of carfentanil in humans are similar to those of other opioids and include euphoria, relaxation, pain relief, pupil constriction, drowsiness, sedation, slowed heart rate, low blood pressure, lowered body temperature, loss of consciousness, and suppression of breathing.^[1] The effects of carfentanil, including overdose, can be reversed by the opioid antagonists naloxone and naltrexone, though higher doses than usual may be necessary compared to other opioids.^[1]^[3]^[4]^: 23 It acts as an ultrapotent and highly selective agonist of the μ-opioid receptor.^[1]

Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceuticals which included Paul Janssen.^[5] It was introduced into veterinary medicine in 1986.^[1] Carfentanil is legally controlled in most jurisdictions.^[3]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Zawilska JB, Kuczyńska K, Kosmal W, Markiewicz K, Adamowicz P (March 2021). "Carfentanil – from an animal anesthetic to a deadly illicit drug". Forensic Science International. 320: 110715. doi:10.1016/j.forsciint.2021.110715. PMID 33581655. S2CID 231918983.
^ "Fentanyl drug profile". EMCDDA.
^ ^a ^b ^c Cite error: The named reference pmid29367860 was invoked but never defined (see the help page).
^ "Report on the risk assessment of methyl 1-(2-phenylethyl)-4-[phenyl(propanoyl) amino]piperidine-4-carboxylate in the framework of the Council Decision on new psychoactive substances" (PDF). European Monitoring Centre for Drugs and Drug Addiction. 8 July 2018.
^ Stanley TH, Egan TD, Van Aken H (February 2008). "A tribute to Dr. Paul A. J. Janssen: entrepreneur extraordinaire, innovative scientist, and significant contributor to anesthesiology". Anesthesia and Analgesia. 106 (2): 451–62, table of contents. doi:10.1213/ane.0b013e3181605add. PMID 18227300. S2CID 20490363.

[pmid33581655-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Zawilska JB, Kuczyńska K, Kosmal W, Markiewicz K, Adamowicz P (March 2021). "Carfentanil – from an animal anesthetic to a deadly illicit drug". Forensic Science International. 320: 110715. doi:10.1016/j.forsciint.2021.110715. PMID 33581655. S2CID 231918983.

[2] "Fentanyl drug profile". EMCDDA.

[pmid29367860-3] Cite error: The named reference pmid29367860 was invoked but never defined (see the help page).

[EMCDDA-4] "Report on the risk assessment of methyl 1-(2-phenylethyl)-4-[phenyl(propanoyl) amino]piperidine-4-carboxylate in the framework of the Council Decision on new psychoactive substances" (PDF). European Monitoring Centre for Drugs and Drug Addiction. 8 July 2018.

[Janssen_Tribute-5] Stanley TH, Egan TD, Van Aken H (February 2008). "A tribute to Dr. Paul A. J. Janssen: entrepreneur extraordinaire, innovative scientist, and significant contributor to anesthesiology". Anesthesia and Analgesia. 106 (2): 451–62, table of contents. doi:10.1213/ane.0b013e3181605add. PMID 18227300. S2CID 20490363.

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