Benzoylfentanyl

Last updated
Benzoylfentanyl
Benzoylfentanyl Structure.svg
Benzoylfentanyl 3D BS.png
Legal status
Legal status
Identifiers
  • N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]benzamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C26H28N2O
Molar mass 384.523 g·mol−1
3D model (JSmol)
  • C1CN(CCC1N(C2=CC=CC=C2)C(=O)C3=CC=CC=C3)CCC4=CC=CC=C4
  • InChI=1S/C26H28N2O/c29-26(23-12-6-2-7-13-23)28(24-14-8-3-9-15-24)25-17-20-27(21-18-25)19-16-22-10-4-1-5-11-22/h1-15,25H,16-21H2
  • Key:BJPDWVPQDSVQKD-UHFFFAOYSA-N

Benzoylfentanyl, also known as phenylfentanyl, is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. [1] [2] In the United States, benzoylfentanyl was first identified in Drug Enforcement Administration drug seizures in 2018. [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]

In the United States, fentanyl-related substances are Schedule I controlled substances. [6] Benzoylfentanyl was banned in Finland in September 2017, [7] and in Sweden in October 2017. [8]

See also

Related Research Articles

4-Phenylfentanyl Opioid analgesic

4-Phenylfentanyl is an opioid analgesic that is a derivative of fentanyl. It was developed during the course of research that ultimately resulted in super-potent opioid derivatives such as carfentanil, though it is a substantially less potent analogue. 4-Phenylfentanyl is around eight times the potency of fentanyl in analgesic tests on animals, but more complex 4-heteroaryl derivatives such as substituted thiophenes and thiazoles are more potent still, as they are closer bioisosteres to the 4-carbomethoxy group of carfentanil.

R-30490 Opioid analgesic

R-30490 is an opioid analgesic related to the highly potent animal tranquilizer carfentanil, and with only slightly lower potency. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs. R-30490 was found to be the most selective agonist for the μ-opioid receptor out of all the fentanyl analogues tested, but it has never been introduced for medical use in humans, although the closely related drug sufentanil is widely used for analgesia and anesthesia during major surgery.

Butyrfentanyl 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.

Benzylfentanyl Chemical compound

Benzylfentanyl (R-4129) is a fentanyl analog. It was temporarily placed in the US Schedule I by emergency scheduling in 1985 due to concerns about its potential for abuse as a designer drug, but this placement was allowed to expire and benzylfentanyl was formally removed from controlled substance listing in 2010, after the DEA's testing determined it to be "essentially inactive" as an opioid. Benzylfentanyl has a Ki of 213 nM at the mu opioid receptor, binding around 1/200 as strong as fentanyl itself, though it is still slightly more potent than codeine.

Furanylfentanyl 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.

Acrylfentanyl Opioid analgesic

Acrylfentanyl (also known as acryloylfentanyl or Egyptenyl) is a highly potent opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. In animal studies the IC50 or half maximal inhibitory concentration for acrylfentanyl to displace naloxone is 1.4 nM, being slightly more potent than fentanyl itself (1.6 nM) as well as having a longer duration of action.

Methoxyacetylfentanyl Opioid analgesic

Methoxyacetylfentanyl, commonly known as MAF is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug.

Tetrahydrofuranylfentanyl Opioid analgesic

Tetrahydrofuranylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug, first appearing in Europe in late 2016.

Orthofluorofentanyl 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.

Cyclopentylfentanyl Opioid analgesic

Cyclopentylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug, mainly in Sweden and other Scandinavian countries.

Valerylfentanyl 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.

4-Chloroisobutyrylfentanyl Opioid analgesic

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

Cyclopropylfentanyl Opioid analgesic

Cyclopropylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. Between June and December 2017, a total of 78 cyclopropylfentanyl-related deaths with analytical confirmation in post-mortem samples were reported by various European countries. Another 115 deaths involving cyclopropylfentanyl were reported from the United States in 2017.

Tetramethylcyclopropylfentanyl Opioid analgesic

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

Benzodioxolefentanyl Opioid analgesic

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

3-Phenylpropanoylfentanyl Opioid analgesic

3-Phenylpropanoylfentanyl (β'-phenylfentanyl) is an opioid analgesic that is an analog of fentanyl, which was invented in 1981, and has been sold as a designer drug, first identified in March 2017 in Sweden.

4-Methylphenethylacetylfentanyl

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

Isofentanyl

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

2,2-Difluorofentanyl

2,2'-Difluorofentanyl is an opioid analgesic that is an analog of fentanyl which has been sold as a designer drug.

References

  1. ↑ Noble, Carolina; Weihe Dalsgaard, Petur; Stybe Johansen, Sys; Linnet, Kristian (2018). "Application of a screening method for fentanyl and its analogues using UHPLC-QTOF-MS with data-independent acquisition (DIA) in MSE mode and retrospective analysis of authentic forensic blood samples". Drug Testing and Analysis. 10 (4): 651–662. doi:10.1002/dta.2263. PMID   28834382.
  2. ↑ Pierzynski HG. Tips for Interpreting GC-MS Fragmentation of Unknown Substituted Fentanyls. Cayman Chemical, 23 August 2017
  3. ↑ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration. Archived from the original (PDF) on 2019-08-01. Retrieved 2019-08-01.
  4. ↑ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (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.
  5. ↑ Armenian P, Vo KT, Barr-Walker J, Lynch KL (2017). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID   29042317. S2CID   21404877.
  6. ↑ 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.
  7. ↑ European Commission. Notification detail. Government Decree amending Annex IV to the Government Decree on substances, preparations and plants to be classified as narcotics The following 9 new substances are classified: 4-chloro-isobutyrfentanyl, 4-Fluoro-isobutyrfentanyl, 3-phenylpropanoylfentanyl, benzodioxole fentanyl, benzoyl fentanyl, cyclopentyl fentanyl, cyclopropyl fentanyl, methoxyacetyl fentanyl and tetramethylcyclopropyane fentanyl. 12 September 2017
  8. ↑ The Public Health Agency of Sweden. 14 nya ämnen kan klassas som narkotika eller hälsofarlig vara. 14 October 2017
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