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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Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos). | 2001 Jun |
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Quantification of brain mu-opioid receptors with [11C]carfentanil: reference-tissue methods. | 2003 Feb |
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In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. | 2004 Apr |
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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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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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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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Effects of ketamine on carfentanil and xylazine immobilization of white-tailed deer (Odocoileus virginianus). | 2006 Sep |
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Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans. | 2007 Feb |
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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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Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects. | 2008 Feb |
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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
by
admin
on
Edited
Mon Mar 31 18:20:55 GMT 2025
by
admin
on
Mon Mar 31 18:20:55 GMT 2025
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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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Preferred Name | English | ||
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Official Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
Classification Tree | Code System | Code | ||
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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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