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Details

Stereochemistry ACHIRAL
Molecular Formula C24H30N2O3
Molecular Weight 394.5066
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARFENTANIL

SMILES

CCC(=O)N(C1=CC=CC=C1)C2(CCN(CCC3=CC=CC=C3)CC2)C(=O)OC

InChI

InChIKey=YDSDEBIZUNNPOB-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Carfentanil is a synthetic fentanyl analog. It is a mu-opioid receptor agonist with an estimated analgesic potency approximately 10,000 times that of morphine and 20-30 times that of fentanyl, based on animal studies. Receptor binding studies have shown that carfentanil binds selectively and competitively to the μ subtype of opioid receptors relative to δ and κ opioid receptors. Preclinical studies have demonstrated that the pharmacodynamic effects, such as analgesia and constipation, produced by carfentanil are similar to other μ opioid agonists. Its extreme potency and propensity to produce rapid and profound respiratory depression has prompted recommendations that an opioid antagonist, such as naloxone or naltrexone, be available whenever carfentanil is used or suspected to be present. Carfentanil (Wildnil) has been used in veterinary as a prescription-only general anesthetic for intramuscular injection in large animals. Carfentanil is no longer FDA-approved for use in animals after Wildlife Laboratories withdrew the application for Wildnil. Carfentanyl is increasingly involved in opioid overdose deaths among illicit opioid users.

Approval Year

PubMed

PubMed

TitleDatePubMed
Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos).
2001 Jun
Sedation and chemical restraint of deer.
2002 Dec
Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET).
2002 Oct
PET imaging of human cardiac opioid receptors.
2002 Oct
Human immobilization: is the experience in Moscow just the beginning?
2003 Jun
Unexpected "gas" casualties in Moscow: a medical toxicology perspective.
2003 May
Pharmacokinetics of carfentanil and naltrexone in domestic goats (Capra hircus).
2004 Dec
What to learn from in vivo opioidergic brain imaging?
2005 Apr
Prolonged central mu-opioid receptor occupancy after single and repeated nalmefene dosing.
2005 Dec
Correlation of stable elevations in striatal mu-opioid receptor availability in detoxified alcoholic patients with alcohol craving: a positron emission tomography study using carbon 11-labeled carfentanil.
2005 Jan
Imaging brain mu-opioid receptors in abstinent cocaine users: time course and relation to cocaine craving.
2005 Jun 15
Effects of ketamine on carfentanil and xylazine immobilization of white-tailed deer (Odocoileus virginianus).
2006 Sep
Pharmacokinetics and pharmacodynamics of carfentanil and naltrexone in female common eland (Taurotragus oryx).
2006 Sep
Buprenorphine duration of action: mu-opioid receptor availability and pharmacokinetic and behavioral indices.
2007 Jan 1
Improving PET receptor binding estimates from Logan plots using principal component analysis.
2008 Apr
Placebo and nocebo effects are defined by opposite opioid and dopaminergic responses.
2008 Feb
Imaging of opioid receptors in the central nervous system.
2008 May
Carfentanil--an ultra potent opioid.
2010 May
Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients.
2010 Oct 15
Patents
Name Type Language
CARFENTANIL
INN  
INN  
Official Name English
R 31833
Code English
CARFENTANYL
Common Name English
(4-CARBOMETHOXY FENTANYL)
Common Name English
carfentanil [INN]
Common Name English
4-PIPERIDINECARBOXYLIC ACID, 4-((1-OXOPROPYL)PHENYLAMINO)-1-(2-PHENYLETHYL)-, METHYL ESTER
Common Name English
4-CARBOMETHOXYFENTANYL
Common Name English
METHYL 1-PHENETHYL-4-(N-PHENYLPROPIONAMIDO)ISONIPECOTATE
Systematic Name English
Classification Tree Code System Code
DEA NO. 9743
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
NCI_THESAURUS C67413
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
Code System Code Type Description
EVMPD
SUB06626MIG
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
DRUG BANK
DB01535
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
WIKIPEDIA
CARFENTANIL
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY Side effects of carfentanil are similar to those of fentanyl, which include itching, nausea and 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. Carfentanil is classified as Schedule II under the Controlled Substances Act in the United States with a DEA ACSCN of 9743 and a 2016 annual aggregate manufacturing quota of 19 grams. In 2016, carfentanil was identified as an additive in heroin sold in Ohio, leading to a spike in the number of overdose cases.
MESH
C017114
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
PUBCHEM
62156
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
FDA UNII
LA9DTA2L8F
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
NCI_THESAURUS
C80574
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
CHEBI
61084
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
ChEMBL
CHEMBL290429
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
INN
4430
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
EPA CompTox
DTXSID40208427
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
CAS
59708-52-0
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY
WEB RESOURCE
CARFENTANIL
Created by admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
PRIMARY