4-Methylphenethylacetylfentanyl

Last updated
4-Methylphenethylacetylfentanyl
4-Methylphenethylacetylfentanyl Structure.svg
Acetylfentanyl-4-methylphenethyl.png
Legal status
Legal status
Identifiers
  • N-[1-[2-(4-Methylphenyl)ethyl]-4-piperidinyl]-N-phenylacetamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C22H28N2O
Molar mass 336.479 g·mol−1
3D model (JSmol)
  • Cc1ccc(cc1)CCN2CCC(CC2)N(C(=O)C)c3ccccc3
  • InChI=1S/C22H28N2O/c1-18-8-10-20(11-9-18)12-15-23-16-13-22(14-17-23)24(19(2)25)21-6-4-3-5-7-21/h3-11,22H,12-17H2,1-2H3
  • Key:BBMRIHXVAUNKEV-UHFFFAOYSA-N

4-Methylphenethylacetylfentanyl (acetylfentanyl 4-methylphenethyl analog) is an opioid analgesic that is an analog (and structural isomer) of fentanyl and has been sold as a designer drug. [2]

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. [3] 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. [4]

In the United States, fentanyl-related substances are Schedule I controlled substances. [5] 4-Methylphenethylacetylfentanyl was explicitly banned in Arkansas in 2018. [6]

See also

Related Research Articles

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

3-Allylfentanyl is an opioid analgesic that is an analogue of fentanyl.

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

Phenaridine (2,5-dimethylfentanyl) is an opioid analgesic that is an analogue of fentanyl. It was developed in 1972, and is used for surgical anasthesia.

<i>beta</i>-Methylfentanyl Opioid analgesic

β-Methylfentanyl is an opioid analgesic that is an analogue of fentanyl.

<span class="mw-page-title-main">4-Phenylfentanyl</span> 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.

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

<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 fifteen 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 as a designer drug. 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 heroin or other opioids. Common 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.

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

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

3-Methylbutyrfentanyl (3-MBF) is an opioid analgesic that is an analog of butyrfentanyl.

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

4-Fluorobutyrylfentanyl (also known as 4-FBF and p-FBF or para-fluorobutyrylfentanyl) is an opioid analgesic that is an analog of butyrfentanyl and has been sold online as a designer drug. It is closely related to 4-fluorofentanyl, which has an EC50 value of 4.2 nM for the human μ-opioid receptor.

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

NFEPP is an analgesic opioid chemical, similar in structure to fentanyl, designed in 2016 by Spahn et al. from Free University of Berlin to avoid the standard negative side effects of opiates, including opioid overdose, by only targeting inflamed tissue.

<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">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">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">Isofentanyl</span> Chemical compound

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> Chemical compound

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

References

  1. 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. Recommended Methods for the Identification and Analysis of Fentanyl and its Analogues in Biological Specimens. United Nations Office on Drugs and Crime, November 2017
  3. 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.
  4. 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.
  5. Drug Enforecement 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.
  6. List of Controlled Substances in Arkansas