Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H30N2O3.C6H8O7 |
Molecular Weight | 586.6301 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.CCC(=O)N(C1=CC=CC=C1)C2(CCN(CCC3=CC=CC=C3)CC2)C(=O)OC
InChI
InChIKey=ZSLYVCXNFQPCGT-UHFFFAOYSA-N
InChI=1S/C24H30N2O3.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-13H,3,14-19H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
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 |
Molecular Formula | C6H8O7 |
Molecular Weight | 192.1235 |
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 |
---|---|---|
A simple synthesis of [11C]carfentanil using an extraction disk instead of HPLC. | 2001 Aug |
|
Regional mu opioid receptor regulation of sensory and affective dimensions of pain. | 2001 Jul 13 |
|
Carfentanil citrate used as an oral anesthetic agent for brown bears (Ursus arctos). | 2001 Jun |
|
Use of naloxone to reverse carfentanil citrate-induced hypoxemia and cardiopulmonary depression in Rocky Mountain wapiti (Cervus elaphus nelsoni). | 2001 Mar |
|
Sedation and chemical restraint of deer. | 2002 Dec |
|
Pain activation of human supraspinal opioid pathways as demonstrated by [11C]-carfentanil and positron emission tomography (PET). | 2002 Oct |
|
PET imaging of human cardiac opioid receptors. | 2002 Oct |
|
Quantification of brain mu-opioid receptors with [11C]carfentanil: reference-tissue methods. | 2003 Feb |
|
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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A comparison of carfentanil/xylazine and Telazol/xylazine for immobilization of white-tailed deer. | 2003 Oct |
|
In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. | 2004 Apr |
|
Pharmacokinetics of carfentanil and naltrexone in domestic goats (Capra hircus). | 2004 Dec |
|
What to learn from in vivo opioidergic brain imaging? | 2005 Apr |
|
Regional mu-opioid receptor binding in insular cortex is decreased in bulimia nervosa and correlates inversely with fasting behavior. | 2005 Aug |
|
Prolonged central mu-opioid receptor occupancy after single and repeated nalmefene dosing. | 2005 Dec |
|
Determination and evaluation of an optimal dosage of carfentanil and xylazine for the immobilization of white-tailed deer (Odocoileus virginianus). | 2005 Jul |
|
Imaging brain mu-opioid receptors in abstinent cocaine users: time course and relation to cocaine craving. | 2005 Jun 15 |
|
Analysis of 13 fentanils, including sufentanil and carfentanil, in human urine by liquid chromatography-atmospheric-pressure ionization-tandem mass spectrometry. | 2006 Jun |
|
Imaging genomics applied to anxiety, stress response, and resiliency. | 2006 Winter |
|
Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans. | 2007 Feb |
|
Buprenorphine duration of action: mu-opioid receptor availability and pharmacokinetic and behavioral indices. | 2007 Jan 1 |
|
Improving PET receptor binding estimates from Logan plots using principal component analysis. | 2008 Apr |
|
Placebo and nocebo effects are defined by opposite opioid and dopaminergic responses. | 2008 Feb |
|
Imaging of opioid receptors in the central nervous system. | 2008 May |
|
Brain mu-opioid receptor binding: relationship to relapse to cocaine use after monitored abstinence. | 2008 Nov |
|
Measurement of central mu-opioid receptor binding in vivo with PET and [11C]carfentanil: a test-retest study in healthy subjects. | 2009 Feb |
|
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 |
|
Human exposures to immobilising agents: results of an online survey. | 2010 Aug 28 |
|
Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine. | 2010 May |
|
Carfentanil--an ultra potent opioid. | 2010 May |
|
Brain mu-opioid receptor binding predicts treatment outcome in cocaine-abusing outpatients. | 2010 Oct 15 |
|
Comparison of thiafenantil-xylazine and carfentanil-xylazine for immobilization of gemsbok (Oryx gazella). | 2010 Sep |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 20:32:36 UTC 2022
by
admin
on
Fri Dec 16 20:32:36 UTC 2022
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Record UNII |
7LG286J8GV
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 522.300
Created by
admin on Fri Dec 16 20:32:36 UTC 2022 , Edited by admin on Fri Dec 16 20:32:36 UTC 2022
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NCI_THESAURUS |
C67413
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admin on Fri Dec 16 20:32:37 UTC 2022 , Edited by admin on Fri Dec 16 20:32:37 UTC 2022
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CHEMBL290429
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DTXSID50976923
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61380-27-6
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7LG286J8GV
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C017114
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C77280
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262-748-6
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DBSALT001611
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9851365
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |