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

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

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

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

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<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

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

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

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<span class="mw-page-title-main">R-30490</span> Opioid analgesic

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<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 15 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 on the illicit drug market. 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 oxycodone, heroin or other opioids. Common side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially fatal respiratory depression. 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

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<span class="mw-page-title-main">Remifentanilic acid</span> Inactive metabolite of remifentanil

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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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