Valerylfentanyl

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Valerylfentanyl
Valerylfentanyl.png
Valerylfentanyl 3D BS.png
Legal status
Legal status
Identifiers
  • N-(1-(2-Phenylethyl)-4-piperidinyl)-N-phenylpentylamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H32N2O
Molar mass 364.533 g·mol−1
3D model (JSmol)
  • CCCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
  • InChI=1S/C24H32N2O/c1-2-3-14-24(27)26(22-12-8-5-9-13-22)23-16-19-25(20-17-23)18-15-21-10-6-4-7-11-21/h4-13,23H,2-3,14-20H2,1H3
  • Key:VCCPXHWAJYWQMR-UHFFFAOYSA-N

Valerylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. [1] 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. [2] In one study, it fully substituted for oxycodone and produced antinociception and oxycodone-like discriminative stimulus effects comparable in potency to morphine in mice, [3] but failed to stimulate locomotor activity in mice at doses up to 100 mg/kg. [4]

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. [5] 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. [6]

Valerylfentanyl is a Schedule I controlled drug in the USA since 1 February 2018. [7]

In December of 2019, the UNODC announced scheduling recommendations placing valerylfentanyl into Schedule I. [8]

See also

Related Research Articles

<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">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">Acrylfentanyl</span> Opioid analgesic

Acrylfentanyl (also known as acryloylfentanyl) 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 (the 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.

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

<span class="mw-page-title-main">Tetrahydrofuranylfentanyl</span> 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.

<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.

<span class="mw-page-title-main">Cyclopentylfentanyl</span> 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.

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

Isobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. It is believed to be around the same potency as butyrfentanyl but has been less widely distributed on illicit markets, though it was one of the earliest of the "new wave" of fentanyl derivatives to appear, and was reported in Europe for the first time in December 2012.

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

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

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

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<span class="mw-page-title-main">Cyclopropylfentanyl</span> 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.

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

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

<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">Benzodioxolefentanyl</span> Opioid analgesic

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

<span class="mw-page-title-main">3-Phenylpropanoylfentanyl</span> 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.

<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.

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

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.

<span class="mw-page-title-main">2,2'-Difluorofentanyl</span> Opioid analgesic designer drug

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

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

Crotonylfentanyl is an opioid analgesic that is an analog of fentanyl and structural isomer of cyclopropylfentanyl and has been sold online as a designer drug. In December 2019, the UNODC announced scheduling recommendations placing crotonylfentanyl into Schedule I.

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

Fentanyl carbamate is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. It has only around 1/10th the potency of fentanyl, but this still makes it a comparatively potent opioid agonist. It falls within the definition of Schedule I drugs in the USA under federal drug analogue legislation, and is specifically listed as a Schedule I drug in North Dakota and Hawaii.

References

  1. ↑ Cooman T, Hoover B, Sauvé B, Bergeron SA, Quinete N, Gardinali P, Arroyo LE (June 2022). "The metabolism of valerylfentanyl using human liver microsomes and zebrafish larvae". Drug Testing and Analysis. 14 (6): 1116–1129. doi:10.1002/dta.3233. PMID   35128825. S2CID   246633284.
  2. ↑ Prekupec MP, Mansky PA, Baumann MH (2017). "Misuse of Novel Synthetic Opioids: A Deadly New Trend". Journal of Addiction Medicine. 11 (4): 256–265. doi:10.1097/ADM.0000000000000324. PMC   5537029 . PMID   28590391.
  3. ↑ Walentiny DM, Moisa LT, Beardsley PM (May 2019). "Oxycodone-like discriminative stimulus effects of fentanyl-related emerging drugs of abuse in mice". Neuropharmacology. 150: 210–216. doi: 10.1016/j.neuropharm.2019.02.007 . PMID   30735691.
  4. ↑ Varshneya NB, Walentiny DM, Moisa LT, Walker TD, Akinfiresoye LR, Beardsley PM (June 2019). "Opioid-like antinociceptive and locomotor effects of emerging fentanyl-related substances". Neuropharmacology. 151: 171–179. doi:10.1016/j.neuropharm.2019.03.023. PMC   8992608 . PMID   30904478. S2CID   84182661.
  5. ↑ 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): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID   25976511.
  6. ↑ Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "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.
  7. ↑ "Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I". Federal Register. 1 February 2018.
  8. ↑ "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
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