Ocfentanil

Overview

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

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, indicating that ocfentanil is approximately 2.5 times as potent as fentanyl in this test.[4] WP

In human volunteers, ocfentanil induces effective analgesia at 1 μg/kg, while at doses up to 3 μg/kg, analgesia and respiratory depression occurred in a dose-dependent manner. One study suggests ocfentanil may be as effective as morphine in post-operative relief, and it has also been studied as a supplement to general anesthesia. 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.[5][6][7] WP

Side effects of fentanyl analogs are similar to those of fentanyl itself, including 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] WP

Legal status

Legal status

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

Ocfentanil has been a Schedule I controlled drug in the USA since February 1, 2018.[11] WP

Chemistry

Formula

C22H27FN2O2 PC

CAS number

101343-69-5 PC

Molar mass (g/mol)

370.5 PC

IUPAC name (computed by PubChem)

N-(2-fluorophenyl)-2-methoxy-N-[1-(2-phenylethyl)piperidin-4-yl]acetamide PC

SMILES

COCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3F PC

InChIKey

NYISTOZKVCMVEL-UHFFFAOYSA-N PC

PubChem CID

60575

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Filer CN, Nugent RP, Huang BS. The synthesis of [fluorophenyl-³H(N)] ocfentanil and [fluorophenyl-³H(N)] brifentanil. Journal of Labelled Compounds and Radiopharmaceuticals. November 1995. doi:10.1002/jlcr.2580361102
2. Other Oral dosage forms
3. Journal / agency Misailidi N, Papoutsis I, Nikolaou P, Dona A, Spiliopoulou C, Athanaselis S. Fentanyls continue to replace heroin in the drug arena: the cases of ocfentanil and carfentanil. Forensic Toxicology. January 2018. doi:10.1007/s11419-017-0379-4 · PMID 29367860 · PMC5754389
4. Journal / agency Bagley JR, Kudzma LV, Lalinde NL, Colapret JA, Huang BS, Lin BS, Jerussi TP, Benvenga MJ, Doorley BM, Ossipov MH. Evolution of the 4-anilidopiperidine class of opioid analgesics. Medicinal Research Reviews. July 1991. doi:10.1002/med.2610110404 · PMID 1875771
5. Journal / agency Glass P, Camporesi E, Martel D, Afifi M. The Analgesic Efficacy of A3217. Anesthesiology. 1989. doi:10.1097/00000542-198909001-00321
6. Journal / agency Fletcher JE, Sebel PS, Murphy MR, Mick SA, Fein S. Comparison of ocfentanil and fentanyl as supplements to general anesthesia. Anesthesia and Analgesia. November 1991. doi:10.1213/00000539-199111000-00019 · PMID 1952145
7. Journal / agency Ebrahim Z. Multiple dose evaluation of the efficacy of ocfentanil hydrochloride (A3217) to produce postoperative analgesia. Anesthesia and Analgesia. 1991. doi:10.1213/00000539-199102001-00001
8. Journal / agency Mounteney J, Giraudon I, Denissov G, Griffiths P. Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe. The International Journal on Drug Policy. July 2015. doi:10.1016/j.drugpo.2015.04.003 · PMID 25976511
9. Journal / agency Dussy FE, Hangartner S, Hamberg C, Berchtold C, Scherer U, Schlotterbeck G, Wyler D, Briellmann TA. An Acute Ocfentanil Fatality: A Case Report with Postmortem Concentrations. Journal of Analytical Toxicology. November 2016. doi:10.1093/jat/bkw096 · PMID 27650310
10. Journal / agency 关于印发《非药用类麻醉药品和精神药品列管办法》的通知. 27 September 2015
11. Other Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I. 1 February 2018

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.