CARFENTANIL CITRATE

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

Structure Search

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)

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30666589 | https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm617007.htm | https://www.who.int/medicines/access/controlled-substances/Critical_Review_Carfentanil.pdf | https://www.cdc.gov/mmwr/volumes/67/wr/mm6727a4.htm

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	11518656
Regional mu opioid receptor regulation of sensory and affective dimensions of pain.	2001 Jul 13	11452128
Use of naloxone to reverse carfentanil citrate-induced hypoxemia and cardiopulmonary depression in Rocky Mountain wapiti (Cervus elaphus nelsoni).	2001 Mar	12790400
Sedation and chemical restraint of deer.	2002 Dec	16032278
Serial immobilization of a Brazilian tapir (Tapirus terrestrus) with oral detomidine and oral carfentanil.	2003 Dec	15077719
Quantification of brain mu-opioid receptors with [11C]carfentanil: reference-tissue methods.	2003 Feb	12623117
Pharmacokinetics of carfentanil and naltrexone in domestic goats (Capra hircus).	2004 Dec	15732589
Mu-opioid receptor binding measured by [11C]carfentanil positron emission tomography is related to craving and mood in alcohol dependence.	2004 Feb 1	14744466
Chemical immobilization of rhebok (Pelea capreolus) with carfentanil-xylazine or etorphine-xylazine.	2004 Sep	15526885
What to learn from in vivo opioidergic brain imaging?	2005 Apr	15737798
Prolonged central mu-opioid receptor occupancy after single and repeated nalmefene dosing.	2005 Dec	15956985
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	15630073
Determination and evaluation of an optimal dosage of carfentanil and xylazine for the immobilization of white-tailed deer (Odocoileus virginianus).	2005 Jul	16244066
Imaging brain mu-opioid receptors in abstinent cocaine users: time course and relation to cocaine craving.	2005 Jun 15	15953495
Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation.	2006 Jun 16	16621415
Dysregulation of endogenous opioid emotion regulation circuitry in major depression in women.	2006 Nov	17088500
Effects of ketamine on carfentanil and xylazine immobilization of white-tailed deer (Odocoileus virginianus).	2006 Sep	17319134
Pharmacokinetics and pharmacodynamics of carfentanil and naltrexone in female common eland (Taurotragus oryx).	2006 Sep	17319131
Imaging genomics applied to anxiety, stress response, and resiliency.	2006 Winter	16595858
Smoking modulation of mu-opioid and dopamine D2 receptor-mediated neurotransmission in humans.	2007 Feb	17091130
Altered central micro-opioid receptor binding after psychological trauma.	2007 May 1	16945349
Time-course of change in [11C]carfentanil and [11C]raclopride binding potential after a nonpharmacological challenge.	2007 Sep	17559096
Improving PET receptor binding estimates from Logan plots using principal component analysis.	2008 Apr	18059434
Placebo and nocebo effects are defined by opposite opioid and dopaminergic responses.	2008 Feb	18250260
Differences in delta- and mu-opioid receptor blockade measured by positron emission tomography in naltrexone-treated recently abstinent alcohol-dependent subjects.	2008 Feb	17487229
Imaging of opioid receptors in the central nervous system.	2008 May	18048446
Brain mu-opioid receptor binding: relationship to relapse to cocaine use after monitored abstinence.	2008 Nov	18762918
Dosimetry of 11C-carfentanil, a micro-opioid receptor imaging agent.	2009 Apr	19242386
A simple modification of GE tracerlab FX C Pro for rapid sequential preparation of [11C]carfentanil and [11C]raclopride.	2009 Apr	19162491
Measurement of central mu-opioid receptor binding in vivo with PET and [11C]carfentanil: a test-retest study in healthy subjects.	2009 Feb	18779961
Positron emission tomography measures of endogenous opioid neurotransmission and impulsiveness traits in humans.	2009 Oct	19805703
Intranasal naltrexone and atipamezole for reversal of white-tailed deer immobilized with carfentanil and medetomidine.	2010 May	20676292

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:34:47 GMT 2023` Edited by `admin` on `Fri Dec 15 16:34:47 GMT 2023`
Record UNII	7LG286J8GV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARFENTANIL CITRATE

Official Name

English

4-PIPERIDINECARBOXYLIC ACID, 4-(1-OXOPROPYL)PHENYLAMINO)1-(2-PHENYLETHYL)-, METHYL ESTER, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)

Common Name

English

CARFENTANIL CITRATE [MART.]

Common Name

English

CARFENTANIL CITRATE [USAN]

Common Name

English

Methyl 1-phenethyl-4-(N-phenylpropionamido)isonipecotate citrate (1:1)

Systematic Name

English

R-33799

Code

English

R 33,799

Code

English

CARFENTANIL CITRATE [GREEN BOOK]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.300