Ocfentanil

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Ocfentanil
Ocfentanil.svg
Ocfentanil 3D BS.png
Clinical data
Other namesOcfentanyl, A-3217
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-(2-Fluorophenyl)-2-methoxy-N-[1-(2-phenylethyl)piperidin-4-yl]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H27FN2O2
Molar mass 370.468 g·mol−1
3D model (JSmol)
  • COCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F
  • InChI=1S/C22H27FN2O2/c1-27-17-22(26)25(21-10-6-5-9-20(21)23)19-12-15-24(16-13-19)14-11-18-7-3-2-4-8-18/h2-10,19H,11-17H2,1H3 X mark.svgN
  • Key:NYISTOZKVCMVEL-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Ocfentanil (INN; also called A-3217) is a potent synthetic opioid structurally related to fentanyl [1] that was developed in the early 1990s as one of a series of potent naloxone-reversible opioids in an attempt to obtain an opioid that had better therapeutic indices in terms of cardiovascular effects and respiratory depression as compared to fentanyl. [2] Ocfentanil was never developed for medical use despite reasonable results in human clinical trials, but subsequently started to be sold as a designer drug starting in around 2013. [3]

Study of the analgesic activity of ocfentanil using the mouse hot plate test (55 °C) gave an ED50 of 0.007 mg/kg compared to 0.018 mg/kg for fentanyl; ocfentanil being approximately 2.5 times as potent as fentanyl in this test. [4]

In human volunteers ocfentanil induces effective analgesia at 1 μg/kg, while in doses up to 3 μg/kg, analgesia and respiratory depression occurred in a dose-dependent manner. While a further study suggests that ocfentanil may be as effective as morphine in post-operative relief, [5] Ocfentanil was also studied as a supplement to general anaesthesia, in which the researchers concluded that it appears to be similar in action to fentanyl, with 3 μg/kg of ocfentanil approximately equivalent to 5 μg/kg of fentanyl. [6] [7]

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. [8] [9]

As of October 2015 Ocfentanil is a controlled substance in China. [10]

Ocfentanil is a Schedule I controlled drug in the USA since 1. February 2018. [11]

Related Research Articles

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Fentanyl, also spelled fentanil, is a highly potent synthetic opioid primarily used as an analgesic. Since 2018, fentanyl and its analogues have been responsible for most drug overdose deaths in the United States, causing over 71,238 deaths in 2021. Because fentanyl is 50 to 100 times more potent than morphine, its primary clinical utility is in pain management for cancer patients and those recovering from painful surgical operations. Fentanyl is also used as a sedative. Depending on the method of delivery, fentanyl can be very fast acting and ingesting a relatively small quantity can cause overdose. Fentanyl works by activating mu-opioid receptors. Fentanyl is also commonly known as fentanyl citrate, Sublimaze, Actiq, Duragesic, Fentora, and Matrifen.

<span class="mw-page-title-main">Carfentanil</span> Chemical compound

Carfentanil or carfentanyl, sold under the brand name Wildnil, is a very potent opioid analgesic which is used in veterinary medicine to anesthetize large animals such as elephants and rhinoceroses. It is typically administered in this context by tranquilizer dart. Carfentanil has also been used in humans for imaging of opioid receptors. It has additionally been used as a recreational drug, typically by injection, insufflation, or inhalation. Deaths have been reported in association with carfentanil.

<span class="mw-page-title-main">Sufentanil</span> Chemical compound

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<span class="mw-page-title-main">Remifentanil</span> Synthetic opioid analgesic

Remifentanil is a potent, short-acting synthetic opioid analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. Remifentanil is used for sedation as well as combined with other medications for use in general anesthesia. The use of remifentanil has made possible the use of high-dose opioid and low-dose hypnotic anesthesia, due to synergism between remifentanil and various hypnotic drugs and volatile anesthetics.

<span class="mw-page-title-main">Nalbuphine</span> Opioid analgesic

Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat.

<span class="mw-page-title-main">Piritramide</span> Synthetic opioid

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<span class="mw-page-title-main">Betahydroxythiofentanyl</span> Chemical compound

Betahydroxythiofentanyl (β-hydroxythiofentanyl) is an opioid analgesic that is an analogue of fentanyl. Beginning as early as 2008, clandestine labs in China began to manufacture synthetic opioids on an industrial scale. Initially, these opioids were distributed in Eastern European markets such as Ukraine and Estonia. Beginning in 2015, fentanyl had replaced heroin as the opioid of choice due to its cheap cost of production and astronomical potency. Utilizing lax regulation in the ports of western Mexico, Mexican and Chinese criminal organizations began to traffic the drug en masse along the US/Mexico border.

<span class="mw-page-title-main">Dihydroetorphine</span> Chemical compound

Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s and is a potent opioid analgesic used mainly in China. It is a derivative of the better-known opioid etorphine, a very potent veterinary painkiller and anesthetic medication used primarily for the sedation of large animals such as elephants, giraffes, and rhinos.

<span class="mw-page-title-main">Trefentanil</span> Chemical compound

Trefentanil (A-3665) is an opioid analgesic that is an analogue of fentanyl and was developed in 1992.

<span class="mw-page-title-main">Dezocine</span> Opioid analgesic

Dezocine, sold under the brand name Dalgan, is an atypical opioid analgesic which is used in the treatment of pain. It is used by intravenous infusion and intramuscular injection.

<span class="mw-page-title-main">Ciramadol</span> Chemical compound

Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s and is related to phencyclidine, tramadol, tapentadol and venlafaxine. It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential and a ceiling on respiratory depression which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine, but is weaker than morphine. Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.

<span class="mw-page-title-main">Etoxadrol</span> Chemical compound

Etoxadrol (CL-1848C) is a dissociative anaesthetic drug that has been found to be an NMDA antagonist and produce similar effects to PCP in animals. Etoxadrol, along with another related drug dexoxadrol, were developed as analgesics for use in humans, but development was discontinued in the late 1970s after patients reported side effects such as nightmares and hallucinations.

<span class="mw-page-title-main">Sameridine</span> Chemical compound

Sameridine is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).

<span class="mw-page-title-main">14-Methoxymetopon</span> Chemical compound

14-Methoxymetopon is an experimental opioid drug developed by a team led by Professor Helmut Schmidhammer at the University of Insbruck in the mid 1990s. It is a derivative of metopon in which a methoxy group has been inserted at the 14-position. It is a highly potent analgesic drug that is around 500 times stronger than morphine when administered systemically; however, when given spinally or supraspinally, it exhibits analgesic activity up to a million fold greater than morphine. It binds strongly to the μ-opioid receptor and activates it to a greater extent than most similar opioid drugs. This produces an unusual pharmacological profile, and although 14-methoxymetopon acts as a potent μ-opioid full agonist in regard to some effects such as analgesia, a ceiling effect is seen on other effects such as constipation and respiratory depression which is believed to involve interaction with the κ-opioid receptor

<span class="mw-page-title-main">Pentamorphone</span> Chemical compound

Pentamorphone is a semi-synthetic opiate derivative related to compounds such as morphine, hydromorphone and oxymorphone. Developed in 1984, it is a potent opioid analgesic several times stronger than fentanyl, and with a similarly fast onset of effects and short duration of action. It was found to produce relatively little respiratory depression compared to other potent opioid agonists, but its analgesic effects were somewhat disappointing in human trials, and while pentamorphone had some slight advantages over fentanyl these were not sufficient to warrant its introduction into clinical use.

<span class="mw-page-title-main">Butyrfentanyl</span> Synthetic opioid analgesic

Butyrfentanyl or butyrylfentanyl is a potent short-acting synthetic opioid analgesic drug. It is an analog of fentanyl with around one quarter of its potency. One of the first mentions of this drug can be found in document written by The College on Problem of Drug Dependence, where it is mentioned as N-butyramide fentanyl analog. This document also states that the article describing its clinical effects was published in 1987. It is an agonist for the μ-opioid receptors.

<span class="mw-page-title-main">Acetylfentanyl</span> Opioid analgesic

Acetylfentanyl is an opioid analgesic drug that is an analog of fentanyl. Studies have estimated acetylfentanyl to be fifteen times more potent than morphine, which would mean that despite being somewhat weaker than fentanyl, it is nevertheless still several times stronger than pure heroin. It has never been licensed for medical use and instead has only been sold as a designer drug. Acetylfentanyl was discovered at the same time as fentanyl itself and had only rarely been encountered on the illicit market in the late 1980s. However, in 2013, Canadian police seized 3 kilograms of acetylfentanyl. As a μ-opioid receptor agonist, acetylfentanyl may serve as a direct substitute for heroin or other opioids. Common 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.

<span class="mw-page-title-main">Furanylfentanyl</span> Opioid analgesic

Furanylfentanyl (Fu-F) is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. It has an ED50 value of 0.02 mg/kg in mice. This makes it approximately one fifth as potent as fentanyl.

<span class="mw-page-title-main">4-Fluorobutyrfentanyl</span> Opioid analgesic

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<span class="mw-page-title-main">Remifentanilic acid</span> Synthetic opioid analgesic

Remifentanilic acid is a metabolite of the potent short-acting synthetic opioid analgesic drug remifentanil. It is an analog of fentanyl and remifentanil, but is not active as an opioid in its own right.

References

  1. ↑ Filer CN, Nugent RP, Huang BS (November 1995). "The synthesis of [fluorophenyl-3H(N)] ocfentanil and [fluorophenyl-3H(N)] brifentanil". Journal of Labelled Compounds and Radiopharmaceuticals. 36 (11): 1019–1027. doi:10.1002/jlcr.2580361102. ISSN   1099-1344.
  2. ↑ US 2002176888,"Oral dosage forms"
  3. ↑ Misailidi N, Papoutsis I, Nikolaou P, Dona A, Spiliopoulou C, Athanaselis S (January 2018). "Fentanyls continue to replace heroin in the drug arena: the cases of ocfentanil and carfentanil". Forensic Toxicology. 36 (1): 12–32. doi:10.1007/s11419-017-0379-4. PMC   5754389 . PMID   29367860.
  4. ↑ Bagley JR, Kudzma LV, Lalinde NL, Colapret JA, Huang BS, Lin BS, et al. (July 1991). "Evolution of the 4-anilidopiperidine class of opioid analgesics". Medicinal Research Reviews. 11 (4): 403–36. doi:10.1002/med.2610110404. PMID   1875771. S2CID   33000913.
  5. ↑ Glass P, Camporesi E, Martel D, Afifi M (1989). "The Analgesic Efficacy of A3217". Anesthesiology. 71 (Supplement): A321. doi:10.1097/00000542-198909001-00321.
  6. ↑ Fletcher JE, Sebel PS, Murphy MR, Mick SA, Fein S (November 1991). "Comparison of ocfentanil and fentanyl as supplements to general anesthesia". Anesthesia and Analgesia. 73 (5): 622–6. doi: 10.1213/00000539-199111000-00019 . PMID   1952145. S2CID   40909537.
  7. ↑ Ebrahim Z (1991). "Multiple dose evaluation of the efficacy of ocfentanil hydrochloride (A3217) to produce postoperative analgesia". Anesthesia and Analgesia. 72: S63. doi:10.1213/00000539-199102001-00001.
  8. ↑ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID   25976511.
  9. ↑ Dussy FE, Hangartner S, Hamberg C, Berchtold C, Scherer U, Schlotterbeck G, et al. (November 2016). "An Acute Ocfentanil Fatality: A Case Report with Postmortem Concentrations". Journal of Analytical Toxicology. 40 (9): 761–766. doi: 10.1093/jat/bkw096 . PMID   27650310.
  10. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  11. ↑ "Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I". Federal Register. 1 February 2018.
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