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Details

Stereochemistry ACHIRAL
Molecular Formula C24H30N2O3.C6H8O7
Molecular Weight 586.6313
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARFENTANIL CITRATE

SMILES

CCC(=O)N(c1ccccc1)C2(CCN(CCc3ccccc3)CC2)C(=O)OC.C(C(=O)O)C(CC(=O)O)(C(=O)O)O

InChI

InChIKey=ZSLYVCXNFQPCGT-UHFFFAOYSA-N
InChI=1S/C24H30N2O3.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-13H,3,14-19H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

HIDE SMILES / InChI

Molecular Formula C6H8O7
Molecular Weight 192.1238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H30N2O3
Molecular Weight 394.5075
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
Use of naloxone to reverse carfentanil citrate-induced hypoxemia and cardiopulmonary depression in Rocky Mountain wapiti (Cervus elaphus nelsoni).
2001 Mar
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
Extraction and quantitation of carfentanil and naltrexone in goat plasma with liquid chromatography-mass spectrometry.
2003 Aug 15
Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil.
2003 Dec
Quantification of brain mu-opioid receptors with [11C]carfentanil: reference-tissue methods.
2003 Feb
Human immobilization: is the experience in Moscow just the beginning?
2003 Jun
Unexpected "gas" casualties in Moscow: a medical toxicology perspective.
2003 May
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
Pharmacokinetics of carfentanil and naltrexone in domestic goats (Capra hircus).
2004 Dec
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
Application of MRI-based partial-volume correction to the analysis of PET images of mu-opioid receptors using statistical parametric mapping.
2004 Mar
Chemical immobilization of rhebok (Pelea capreolus) with carfentanil-xylazine or etorphine-xylazine.
2004 Sep
A review of drugs and techniques used for sedation and anaesthesia in captive rhinoceros species.
2004 Sep
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
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
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
Analysis of 13 fentanils, including sufentanil and carfentanil, in human urine by liquid chromatography-atmospheric-pressure ionization-tandem mass spectrometry.
2006 Jun
Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation.
2006 Jun 16
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
Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans.
2007 Feb
Buprenorphine duration of action: mu-opioid receptor availability and pharmacokinetic and behavioral indices.
2007 Jan 1
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
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 Fri Jun 25 22:32:31 UTC 2021
Edited
by admin
on Fri Jun 25 22:32:31 UTC 2021
Record UNII
7LG286J8GV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARFENTANIL CITRATE
GREEN BOOK   MART.   USAN  
USAN  
Official Name English
4-PIPERIDINECARBOXYLIC ACID, 4-(1-OXOPROPYL)PHENYLAMINO)1-(2-PHENYLETHYL)-, METHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Common Name English
CARFENTANIL CITRATE [MART.]
Common Name English
CARFENTANIL CITRATE [USAN]
Common Name English
METHYL 1-PHENETHYL-4-(N-PHENYLPROPIONAMIDO)ISONIPECOTATE CITRATE (1:1)
Systematic Name English
R-33799
Code English
R 33,799
Code English
CARFENTANIL CITRATE [GREEN BOOK]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.300
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
NCI_THESAURUS C67413
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL290429
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
CAS
61380-27-6
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
FDA UNII
7LG286J8GV
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
MESH
C017114
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
NCI_THESAURUS
C77280
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
262-748-6
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
DRUG BANK
DBSALT001611
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
PUBCHEM
9851365
Created by admin on Fri Jun 25 22:32:31 UTC 2021 , Edited by admin on Fri Jun 25 22:32:31 UTC 2021
PRIMARY
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ACTIVE MOIETY