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
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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Regional mu opioid receptor regulation of sensory and affective dimensions of pain. | 2001 Jul 13 |
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Use of naloxone to reverse carfentanil citrate-induced hypoxemia and cardiopulmonary depression in Rocky Mountain wapiti (Cervus elaphus nelsoni). | 2001 Mar |
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Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil. | 2003 Dec |
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In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. | 2004 Apr |
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Determination and evaluation of an optimal dosage of carfentanil and xylazine for the immobilization of white-tailed deer (Odocoileus virginianus). | 2005 Jul |
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Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation. | 2006 Jun 16 |
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Imaging genomics applied to anxiety, stress response, and resiliency. | 2006 Winter |
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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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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 |
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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
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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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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
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