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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A simple synthesis of [11C]carfentanil using an extraction disk instead of HPLC. | 2001 Aug |
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Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos). | 2001 Jun |
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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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Sedation and chemical restraint of deer. | 2002 Dec |
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PET imaging of human cardiac opioid receptors. | 2002 Oct |
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Extraction and quantitation of carfentanil and naltrexone in goat plasma with liquid chromatography-mass spectrometry. | 2003 Aug 15 |
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Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil. | 2003 Dec |
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Quantification of brain mu-opioid receptors with [11C]carfentanil: reference-tissue methods. | 2003 Feb |
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Human immobilization: is the experience in Moscow just the beginning? | 2003 Jun |
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Unexpected "gas" casualties in Moscow: a medical toxicology perspective. | 2003 May |
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Regulation of human affective responses by anterior cingulate and limbic mu-opioid neurotransmission. | 2003 Nov |
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A comparison of carfentanil/xylazine and Telazol/xylazine for immobilization of white-tailed deer. | 2003 Oct |
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In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. | 2004 Apr |
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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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Application of MRI-based partial-volume correction to the analysis of PET images of mu-opioid receptors using statistical parametric mapping. | 2004 Mar |
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Chemical immobilization of rhebok (Pelea capreolus) with carfentanil-xylazine or etorphine-xylazine. | 2004 Sep |
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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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What to learn from in vivo opioidergic brain imaging? | 2005 Apr |
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Prolonged central mu-opioid receptor occupancy after single and repeated nalmefene dosing. | 2005 Dec |
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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 |
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Imaging brain mu-opioid receptors in abstinent cocaine users: time course and relation to cocaine craving. | 2005 Jun 15 |
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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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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 |
|
Imaging genomics applied to anxiety, stress response, and resiliency. | 2006 Winter |
|
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 |
|
Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects. | 2008 Feb |
|
Brain mu-opioid receptor binding: relationship to relapse to cocaine use after monitored abstinence. | 2008 Nov |
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Dosimetry of 11C-carfentanil, a micro-opioid receptor imaging agent. | 2009 Apr |
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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 |
|
Dysregulation of regional endogenous opioid function in borderline personality disorder. | 2010 Aug |
|
Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine. | 2010 May |
|
Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients. | 2010 Oct 15 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 19:26:56 UTC 2022
by
admin
on
Fri Dec 16 19:26:56 UTC 2022
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Record UNII |
LA9DTA2L8F
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Record Status |
Validated (UNII)
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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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Code System | Code | Type | Description | ||
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SUB06626MIG
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DB01535
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CARFENTANIL
Created by
admin on Fri Dec 16 19:26:56 UTC 2022 , Edited by admin on Fri Dec 16 19:26:56 UTC 2022
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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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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
Created by
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |