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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
Regional mu opioid receptor regulation of sensory and affective dimensions of pain.
2001 Jul 13
Use of naloxone to reverse carfentanil citrate-induced hypoxemia and cardiopulmonary depression in Rocky Mountain wapiti (Cervus elaphus nelsoni).
2001 Mar
Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil.
2003 Dec
In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor.
2004 Apr
Determination and evaluation of an optimal dosage of carfentanil and xylazine for the immobilization of white-tailed deer (Odocoileus virginianus).
2005 Jul
Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation.
2006 Jun 16
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
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
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 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
WIKIPEDIA List_of_fentanyl_analogues
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NCI_THESAURUS C67413
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Code System Code Type Description
EVMPD
SUB06626MIG
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PRIMARY
DRUG BANK
DB01535
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PRIMARY
WIKIPEDIA
CARFENTANIL
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 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
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MESH
C017114
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PUBCHEM
62156
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FDA UNII
LA9DTA2L8F
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NCI_THESAURUS
C80574
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CHEBI
61084
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ChEMBL
CHEMBL290429
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INN
4430
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EPA CompTox
DTXSID40208427
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CAS
59708-52-0
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
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WEB RESOURCE
CARFENTANIL
Created by admin on Fri Dec 15 16:10:30 GMT 2023 , Edited by admin on Fri Dec 15 16:10:30 GMT 2023
PRIMARY