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
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
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
Title | Date | PubMed |
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PET imaging of the opioid receptor: the early years. | 2001 Jul |
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A comparison of carfentanil/xylazine and Telazol/xylazine for immobilization of white-tailed deer. | 2003 Oct |
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Pharmacokinetics of carfentanil and naltrexone in domestic goats (Capra hircus). | 2004 Dec |
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Studies of the mechanism of the in-loop synthesis of radiopharmaceuticals. | 2004 Dec |
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Mu-opioid receptor binding measured by [11C]carfentanil positron emission tomography is related to craving and mood in alcohol dependence. | 2004 Feb 1 |
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A review of drugs and techniques used for sedation and anaesthesia in captive rhinoceros species. | 2004 Sep |
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Analysis of 13 fentanils, including sufentanil and carfentanil, in human urine by liquid chromatography-atmospheric-pressure ionization-tandem mass spectrometry. | 2006 Jun |
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Dysregulation of endogenous opioid emotion regulation circuitry in major depression in women. | 2006 Nov |
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Pharmacokinetics and pharmacodynamics of carfentanil and naltrexone in female common eland (Taurotragus oryx). | 2006 Sep |
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Altered central micro-opioid receptor binding after psychological trauma. | 2007 May 1 |
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Time-course of change in [11C]carfentanil and [11C]raclopride binding potential after a nonpharmacological challenge. | 2007 Sep |
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Improving PET receptor binding estimates from Logan plots using principal component analysis. | 2008 Apr |
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A simple modification of GE tracerlab FX C Pro for rapid sequential preparation of [11C]carfentanil and [11C]raclopride. | 2009 Apr |
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Positron emission tomography measures of endogenous opioid neurotransmission and impulsiveness traits in humans. | 2009 Oct |
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Dysregulation of regional endogenous opioid function in borderline personality disorder. | 2010 Aug |
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Human exposures to immobilising agents: results of an online survey. | 2010 Aug 28 |
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Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine. | 2010 May |
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Carfentanil--an ultra potent opioid. | 2010 May |
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Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients. | 2010 Oct 15 |
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Comparison of thiafenantil-xylazine and carfentanil-xylazine for immobilization of gemsbok (Oryx gazella). | 2010 Sep |
Patents
Substance Class |
Chemical
Created
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Fri Dec 15 16:10:30 GMT 2023
by
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on
Fri Dec 15 16:10:30 GMT 2023
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Record UNII |
LA9DTA2L8F
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Record Status |
Validated (UNII)
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Record Version |
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DEA NO. |
9743
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WIKIPEDIA |
List_of_fentanyl_analogues
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NCI_THESAURUS |
C67413
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SUB06626MIG
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DB01535
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CARFENTANIL
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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. | ||
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100000084592
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C017114
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62156
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LA9DTA2L8F
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C80574
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61084
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CHEMBL290429
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4430
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DTXSID40208427
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59708-52-0
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CARFENTANIL
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
IC50 of Fentanyl= 1.23 NM
IC50
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
MAJOR
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METABOLITE ACTIVE -> PARENT |
Liver microsomes many CYP Enzymes catalyze reaction.
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METABOLITE ACTIVE -> PARENT |
More active than Carfentanil.
MINOR
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METABOLITE ACTIVE -> PARENT |
Liver microsomes many CYP Enzymes catalyze reaction.
MAJOR
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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