U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C24H30N2O3
Molecular Weight 394.5066
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Sedation and chemical restraint of deer.
2002 Dec
Extraction and quantitation of carfentanil and naltrexone in goat plasma with liquid chromatography-mass spectrometry.
2003 Aug 15
Regulation of human affective responses by anterior cingulate and limbic mu-opioid neurotransmission.
2003 Nov
A comparison of carfentanil/xylazine and Telazol/xylazine for immobilization of white-tailed deer.
2003 Oct
In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor.
2004 Apr
What to learn from in vivo opioidergic brain imaging?
2005 Apr
Regional mu-opioid receptor binding in insular cortex is decreased in bulimia nervosa and correlates inversely with fasting behavior.
2005 Aug
Determination and evaluation of an optimal dosage of carfentanil and xylazine for the immobilization of white-tailed deer (Odocoileus virginianus).
2005 Jul
Imaging brain mu-opioid receptors in abstinent cocaine users: time course and relation to cocaine craving.
2005 Jun 15
Dysregulation of endogenous opioid emotion regulation circuitry in major depression in women.
2006 Nov
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
Imaging genomics applied to anxiety, stress response, and resiliency.
2006 Winter
Time-course of change in [11C]carfentanil and [11C]raclopride binding potential after a nonpharmacological challenge.
2007 Sep
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
Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects.
2008 Feb
Imaging of opioid receptors in the central nervous system.
2008 May
Brain mu-opioid receptor binding: relationship to relapse to cocaine use after monitored abstinence.
2008 Nov
Dosimetry of 11C-carfentanil, a micro-opioid receptor imaging agent.
2009 Apr
A simple modification of GE tracerlab FX C Pro for rapid sequential preparation of [11C]carfentanil and [11C]raclopride.
2009 Apr
Measurement of central mu-opioid receptor binding in vivo with PET and [11C]carfentanil: a test-retest study in healthy subjects.
2009 Feb
Physiologic effects of nasal oxygen or medical air administered prior to and during carfentanil-xylazine anesthesia in North American elk (Cervus canadensis manitobensis).
2009 Mar
Positron emission tomography measures of endogenous opioid neurotransmission and impulsiveness traits in humans.
2009 Oct
Dysregulation of regional endogenous opioid function in borderline personality disorder.
2010 Aug
Human exposures to immobilising agents: results of an online survey.
2010 Aug 28
Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine.
2010 May
Carfentanil--an ultra potent opioid.
2010 May
Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients.
2010 Oct 15
Comparison of thiafenantil-xylazine and carfentanil-xylazine for immobilization of gemsbok (Oryx gazella).
2010 Sep
Patents
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:38:08 UTC 2023
Edited
by admin
on Wed Jul 05 23:38:08 UTC 2023
Record UNII
LA9DTA2L8F
Record Status Validated (UNII)
Record Version
  • Download
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 Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
NCI_THESAURUS C67413
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
Code System Code Type Description
EVMPD
SUB06626MIG
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
DRUG BANK
DB01535
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
WIKIPEDIA
CARFENTANIL
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
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.
SMS_ID
100000084592
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
MESH
C017114
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
PUBCHEM
62156
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
FDA UNII
LA9DTA2L8F
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
NCI_THESAURUS
C80574
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
CHEBI
61084
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL290429
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
INN
4430
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID40208427
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
CAS
59708-52-0
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
WEB RESOURCE
CARFENTANIL
Created by admin on Wed Jul 05 23:38:08 UTC 2023 , Edited by admin on Wed Jul 05 23:38:08 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
IC50 of Fentanyl= 1.23 NM
IC50
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE INACTIVE -> PARENT
MAJOR
METABOLITE ACTIVE -> PARENT
Liver microsomes many CYP Enzymes catalyze reaction.
METABOLITE ACTIVE -> PARENT
Liver microsomes many CYP Enzymes catalyze reaction.
MAJOR
Related Record Type Details
ACTIVE MOIETY