Carfentanil: Difference between revisions

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	'''Carfentanil''' or '''carfentanyl''' (also known as '''4-carbomethoxyfentanyl''') is an ] of the synthetic ] ] ]. It was found to be four orders of magnitude or 10,000 times more potent than ], making it one of the most potent known and the most potent commercially used ~~opioid~~.<ref>{{cite web \| url=http://www.emcdda.europa.eu/publications/drug-profiles/fentanyl \| title=Fentanyl drug profile \| publisher=EMCDDA}}</ref> Carfentanil was first synthesized in 1974 by a team of chemists at ] which included ].<ref>{{cite journal\|first1=Theodore H.\|last1=Stanley\|first2=Talmage D.\|last2=Egan\|first3=Hugo Van\|last3=Aken\|title=A Tribute to Dr. Paul A. J. Janssen: Entrepreneur Extraordinaire, Innovative Scientist, and Significant Contributor to Anesthesiology\|url=http://journals.lww.com/anesthesia-analgesia/pages/articleviewer.aspx?year=2008&issue=02000&article=00016&type=Fulltext\|journal=Anesthesia & Analgesia\|pages=451–462\|volume=106\|issue=2\|doi=10.1213/ane.0b013e3181605add\|pmid=18227300\|date=February 2008}}</ref> It is marketed under the trade name '''Wildnil''' as a ] agent for large animals.<ref>{{cite journal\|first1=V. De\|last1=Vos\|title=Immobilisation of free-ranging wild animals using a new drug\|url=http://veterinaryrecord.bmj.com/content/103/4/64\|journal=Veterinary Record\|date=22 July 1978\|issn=2042-7670\|pages=64–68\|volume=103\|issue=4\|pmid=685103\|doi=10.1136/vr.103.4.64}}</ref>		'''Carfentanil''' or '''carfentanyl''' (also known as '''4-carbomethoxyfentanyl''') is an ] of the synthetic ] ] ]. It was found to be four orders of magnitude or 10,000 times more potent than ], making it one of the most potent known and the most potent commercially used opioids.<ref>{{cite web \| url=http://www.emcdda.europa.eu/publications/drug-profiles/fentanyl \| title=Fentanyl drug profile \| publisher=EMCDDA}}</ref> Carfentanil was first synthesized in 1974 by a team of chemists at ] which included ].<ref>{{cite journal\|first1=Theodore H.\|last1=Stanley\|first2=Talmage D.\|last2=Egan\|first3=Hugo Van\|last3=Aken\|title=A Tribute to Dr. Paul A. J. Janssen: Entrepreneur Extraordinaire, Innovative Scientist, and Significant Contributor to Anesthesiology\|url=http://journals.lww.com/anesthesia-analgesia/pages/articleviewer.aspx?year=2008&issue=02000&article=00016&type=Fulltext\|journal=Anesthesia & Analgesia\|pages=451–462\|volume=106\|issue=2\|doi=10.1213/ane.0b013e3181605add\|pmid=18227300\|date=February 2008}}</ref> It is marketed under the trade name '''Wildnil''' as a ] agent for large animals.<ref>{{cite journal\|first1=V. De\|last1=Vos\|title=Immobilisation of free-ranging wild animals using a new drug\|url=http://veterinaryrecord.bmj.com/content/103/4/64\|journal=Veterinary Record\|date=22 July 1978\|issn=2042-7670\|pages=64–68\|volume=103\|issue=4\|pmid=685103\|doi=10.1136/vr.103.4.64}}</ref>

	Side effects of ] analogs are similar to those of fentanyl itself, which include ], ] and potentially serious ], 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.<ref>{{cite journal\|first1=Jane\|last1=Mounteney\|first2=Isabelle\|last2=Giraudon\|first3=Gleb\|last3=Denissov\|first4=Paul\|last4=Griffiths\|title=Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe\|url=http://www.sciencedirect.com/science/article/pii/S0955395915000973\|journal=International Journal of Drug Policy\|date=July 2015\|pages=626–631\|volume=26\|issue=7\|doi=10.1016/j.drugpo.2015.04.003\|pmid=25976511}}</ref>		Side effects of ] analogs are similar to those of fentanyl itself, which include ], ] and potentially serious ], 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.<ref>{{cite journal\|first1=Jane\|last1=Mounteney\|first2=Isabelle\|last2=Giraudon\|first3=Gleb\|last3=Denissov\|first4=Paul\|last4=Griffiths\|title=Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe\|url=http://www.sciencedirect.com/science/article/pii/S0955395915000973\|journal=International Journal of Drug Policy\|date=July 2015\|pages=626–631\|volume=26\|issue=7\|doi=10.1016/j.drugpo.2015.04.003\|pmid=25976511}}</ref>

Revision as of 14:37, 2 September 2016

Pharmaceutical compound

Carfentanil
Clinical data

Trade names	Wildnil
ATC code	none
Legal status
Legal status	AU: S8 (Controlled drug) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule II In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	7.7 hrs
Identifiers
IUPAC name 4-((1-oxopropyl)-phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid methyl ester
CAS Number	59708-52-0
PubChem CID	62156
DrugBank	DB01535
ChemSpider	55986
UNII	LA9DTA2L8F
ChEBI	CHEBI:61084
ChEMBL	ChEMBL290429
CompTox Dashboard (EPA)	DTXSID40208427
ECHA InfoCard	100.352.183
Chemical and physical data
Formula	C₂₄H₃₀N₂O₃
Molar mass	394.514 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(C1(CCN(CC1)CCC2=CC=CC=C2)N(C(CC)=O)C3=CC=CC=C3)OC
InChI 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 Key:YDSDEBIZUNNPOB-UHFFFAOYSA-N
(verify)

Carfentanil or carfentanyl (also known as 4-carbomethoxyfentanyl) is an analog of the synthetic opioid analgesic fentanyl. It was found to be four orders of magnitude or 10,000 times more potent than morphine, making it one of the most potent known and the most potent commercially used opioids. Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceutica which included Paul Janssen. It is marketed under the trade name Wildnil as a general anaesthetic agent for large animals.

Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious 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.

In August 2016, heroin contaminated with carfentanil was reported in Florida, Indiana, West Virginia, and Ohio; possibly contributing to overdoses.

Carfentanil is a Schedule II Narcotic controlled substance in the United States with a DEA ACSCN of 9743 and a 2016 annual aggregate manufacturing quota of 19 grams, unchanged from the prior year.

Moscow theater hostage crisis

Main article: Moscow theater hostage crisis

A 2012 study found evidence supporting the claim that during the 2002 Moscow theater hostage crisis, the Russian military made use of an aerosol form of carfentanil and another similar drug, remifentanil, to subdue Chechen hostage takers. Its short action, easy reversibility and therapeutic index (10,600 vs. 300 for fentanyl) would make it a potential agent for this purpose. Riches, et al., found evidence from liquid chromatography-tandem mass spectrometry analysis of extracts of clothing from two British survivors, and urine from a third survivor, that the aerosol contained a mixture of the two anesthetics, the exact proportions of which the study was unable to determine. Previously, Wax et al. had surmised from the available evidence that the Moscow emergency services had not been informed of the use of the agent, but were instructed to bring opioid antagonists. Because of the lack of information provided, the emergency workers did not bring adequate supplies of naloxone (opioid inverse agonist) or naltrexone (opioid antagonist) to prevent complications in many of the victims and there were subsequently over 125 confirmed deaths from both respiratory failure and aerosol inhalation during the incident. Assuming that carfentanil and remifentanil were the only active constituents, which has not been verified by the Russian military, the primary acute toxic effect to the theater victims would have been opioid-induced apnea; in this case mechanical ventilation or treatment with opioid antagonists could have been life-saving for many victims.

References

"Fentanyl drug profile". EMCDDA.
Stanley, Theodore H.; Egan, Talmage D.; Aken, Hugo Van (February 2008). "A Tribute to Dr. Paul A. J. Janssen: Entrepreneur Extraordinaire, Innovative Scientist, and Significant Contributor to Anesthesiology". Anesthesia & Analgesia. 106 (2): 451–462. doi:10.1213/ane.0b013e3181605add. PMID 18227300.
Vos, V. De (22 July 1978). "Immobilisation of free-ranging wild animals using a new drug". Veterinary Record. 103 (4): 64–68. doi:10.1136/vr.103.4.64. ISSN 2042-7670. PMID 685103.
Mounteney, Jane; Giraudon, Isabelle; Denissov, Gleb; Griffiths, Paul (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
Kounang, Nadia; Marco, Tony (25 August 2016). "Heroin laced with elephant tranquilizer hits the streets". CNN. Retrieved 26 August 2016.
"Established Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2016". Federal Register. 6 October 2015.
Riches, James R.; Read, Robert W.; Black, Robin M.; Cooper, Nicholas J.; Timperley, Christopher M. (November 2012). "Analysis of Clothing and Urine from Moscow Theatre Siege Casualties Reveals Carfentanil and Remifentanil Use". Journal of Analytical Toxicology. 36 (9): 647–656. doi:10.1093/jat/bks078. ISSN 1945-2403. PMID 23002178.
Wax, Paul M.; Becker, Charles E.; Curry, Steven C. (May 2003). "Unexpected "gas" casualties in Moscow: A medical toxicology perspective". Annals of Emergency Medicine. 41 (5): 700–705. doi:10.1067/mem.2003.148. PMID 12712038.

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine +aspirin +paracetamol Morphine (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen Fenoprofen Flurbiprofen Ibuprofen (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib Parecoxib Rofecoxib Valdecoxib
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid) (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone