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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

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
Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos).
2001 Jun
Quantification of brain mu-opioid receptors with [11C]carfentanil: reference-tissue methods.
2003 Feb
In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor.
2004 Apr
Studies of the mechanism of the in-loop synthesis of radiopharmaceuticals.
2004 Dec
Mu-opioid receptor binding measured by [11C]carfentanil positron emission tomography is related to craving and mood in alcohol dependence.
2004 Feb 1
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
Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation.
2006 Jun 16
Effects of ketamine on carfentanil and xylazine immobilization of white-tailed deer (Odocoileus virginianus).
2006 Sep
Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans.
2007 Feb
Altered central micro-opioid receptor binding after psychological trauma.
2007 May 1
Time-course of change in [11C]carfentanil and [11C]raclopride binding potential after a nonpharmacological challenge.
2007 Sep
Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects.
2008 Feb
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 Mon Mar 31 18:20:55 GMT 2025
Edited
by admin
on Mon Mar 31 18:20:55 GMT 2025
Record UNII
LA9DTA2L8F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
R 31833
Preferred Name English
Carfentanil
INN  
INN  
Official Name 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 Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
Code System Code Type Description
EVMPD
SUB06626MIG
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
DRUG BANK
DB01535
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
WIKIPEDIA
CARFENTANIL
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
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 Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
MESH
C017114
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
PUBCHEM
62156
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
FDA UNII
LA9DTA2L8F
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
NCI_THESAURUS
C80574
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
CHEBI
61084
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
ChEMBL
CHEMBL290429
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
INN
4430
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID40208427
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
CAS
59708-52-0
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
PRIMARY
WEB RESOURCE
CARFENTANIL
Created by admin on Mon Mar 31 18:20:55 GMT 2025 , Edited by admin on Mon Mar 31 18:20:55 GMT 2025
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
More active than Carfentanil.
MINOR
METABOLITE ACTIVE -> PARENT
Liver microsomes many CYP Enzymes catalyze reaction.
MAJOR
Related Record Type Details
ACTIVE MOIETY