Isofentanyl

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Isofentanyl
Isofentanyl Structure.svg
Isofentanyl 3D BS.png
Legal status
Legal status
Identifiers
  • N-(1-Benzyl-3-methylpiperidin-4-yl)-N-phenylpropanamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H28N2O
Molar mass 336.479 g·mol−1
3D model (JSmol)
  • c2ccccc2N(C(=O)CC)C1CCN(CC1C)Cc3ccccc3

Isofentanyl (3-methyl-benzylfentanyl) is an opioid analgesic that is an analog (and structural isomer) of fentanyl first invented in 1973, [2] and which has been sold as a designer drug. [3]

Contents

Side effects

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. [4] A new wave of fentanyl analogues and associated deaths began in around 2014 in the US, and have continued to grow in prevalence; especially since 2016 these drugs have been responsible for hundreds of overdose deaths every week. [5]

As a structural isomer of fentanyl itself, isofentanyl is banned under drug analogue laws in many jurisdictions around the world. In the United States, fentanyl-related substances are Schedule I controlled substances. [1]

See also

Related Research Articles

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<span class="mw-page-title-main">3-Methylthiofentanyl</span> Opioid analgesic

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<span class="mw-page-title-main">3-Allylfentanyl</span> Opioid analgesic

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

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

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

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<span class="mw-page-title-main">3-Methylbutyrfentanyl</span> Opioid analgesic

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

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

Orthofluorofentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. While the structural isomer p-fluorofentanyl was one of the first illicit fentanyl analogues identified in 1981, Orthofluorofentanyl did not appear on the illicit market until August 2016.

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

Valerylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. It has been seldom reported on illicit markets and there is little information about it, though it is believed to be less potent than butyrfentanyl but more potent than benzylfentanyl. In one study, it fully substituted for oxycodone and produced antinociception and oxycodone-like discriminative stimulus effects comparable in potency to morphine in mice, but failed to stimulate locomotor activity in mice at doses up to 100 mg/kg.

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

Tetramethylcyclopropylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.

<span class="mw-page-title-main">4-Methylphenethylacetylfentanyl</span> Chemical compound

4-Methylphenethylacetylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.

References

  1. 1 2 Drug Enforcement Administration, Department of Justice (2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID   29932611.
  2. ↑ Riley TN, Hale DB, Wilson MC (June 1973). "4-Anilidopiperidine analgesics. I. Synthesis and analgesic activity of certain ring-methylated 1-substituted 4-propananilidopiperidines". Journal of Pharmaceutical Sciences. 62 (6): 983–6. doi:10.1002/jps.2600620627. PMID   4712637.
  3. ↑ Meyer MR, Dinger J, Schwaninger AE, Wissenbach DK, Zapp J, Fritschi G, Maurer HH (January 2012). "Qualitative studies on the metabolism and the toxicological detection of the fentanyl-derived designer drugs 3-methylfentanyl and isofentanyl in rats using liquid chromatography-linear ion trap-mass spectrometry (LC-MS(n))". Analytical and Bioanalytical Chemistry. 402 (3): 1249–55. doi:10.1007/s00216-011-5528-8. PMID   22065349. S2CID   329682.
  4. ↑ 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.
  5. ↑ Armenian P, Vo KT, Barr-Walker J, Lynch KL (October 2017). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review" (PDF). Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID   29042317. S2CID   21404877.
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