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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Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos). | 2001 Jun |
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Sedation and chemical restraint of deer. | 2002 Dec |
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Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET). | 2002 Oct |
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PET imaging of human cardiac opioid receptors. | 2002 Oct |
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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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Pharmacokinetics of carfentanil and naltrexone in domestic goats (Capra hircus). | 2004 Dec |
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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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Effects of ketamine on carfentanil and xylazine immobilization of white-tailed deer (Odocoileus virginianus). | 2006 Sep |
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Pharmacokinetics and pharmacodynamics of carfentanil and naltrexone in female common eland (Taurotragus oryx). | 2006 Sep |
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Buprenorphine duration of action: mu-opioid receptor availability and pharmacokinetic and behavioral indices. | 2007 Jan 1 |
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Improving PET receptor binding estimates from Logan plots using principal component analysis. | 2008 Apr |
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Placebo and nocebo effects are defined by opposite opioid and dopaminergic responses. | 2008 Feb |
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Imaging of opioid receptors in the central nervous system. | 2008 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 |
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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Code System | Code | Type | Description | ||
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SUB06626MIG
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DB01535
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CARFENTANIL
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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
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)