Benzylfentanyl

Last updated
Benzylfentanyl
Benzylfentanyl.svg
Benzylfentanyl.png
Names
Preferred IUPAC name
N-(1-Benzylpiperidin-4-yl)-N-phenylpropanamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.559 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C21H26N2O/c1-2-21(24)23(19-11-7-4-8-12-19)20-13-15-22(16-14-20)17-18-9-5-3-6-10-18/h3-12,20H,2,13-17H2,1H3
    Key: POQDXIFVWVZVML-UHFFFAOYSA-N
  • CCC(=O)N(C1CCN(CC1)CC2=CC=CC=C2)C3=CC=CC=C3
Properties
C21H26N2O
Molar mass 322.452 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benzylfentanyl (R-4129) is a fentanyl analog. [1] 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. [2] Benzylfentanyl has a Ki of 213 nM at the mu opioid receptor, binding around 1/200 as strong as fentanyl itself, [3] though it is still slightly more potent than codeine. [4]

Contents

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]

In the United States, fentanyl-related substances are Schedule I controlled substances. [6] Benzylfentanyl is illegal in Germany (Anlage I)

See also

Related Research Articles

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Lofentanil is one of the most potent opioid analgesics known and is an analogue of fentanyl, which was developed in 1960. It is most similar to the highly potent opioid carfentanil (4-carbomethoxyfentanyl), only slightly more potent. Lofentanil can be described as 3-methylcarfentanil, or 3-methyl-4-carbomethoxyfentanyl. While 3-methylfentanyl is considerably more potent than fentanyl itself, lofentanil is only slightly stronger than carfentanil. This suggests that substitution at both the 3 and 4 positions of the piperidine ring introduces steric hindrance which prevents μ-opioid affinity from increasing much further. As with other 3-substituted fentanyl derivatives such as ohmefentanyl, the stereoisomerism of lofentanil is very important, with some stereoisomers being much more potent than others.

3-Allylfentanyl Opioid analgesic

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

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

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

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.

Acetylfentanyl 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.

3-Methylbutyrfentanyl Opioid analgesic

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

4-Fluorobutyrfentanyl 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.

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.

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.

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.

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. ↑ Ruangyuttikarn, W; Law, MY; Rollins, DE; Moody, DE (1990). "Detection of fentanyl and its analogs by enzyme-linked immunosorbent assay". Journal of Analytical Toxicology. 14 (3): 160–4. doi:10.1093/jat/14.3.160. PMID   2374405.
  2. ↑ Correction of Code of Federal Regulations: Removal of Temporary Listing of Benzylfentanyl and Thenylfentanyl as Controlled Substances
  3. ↑ Utilization of a radioreceptor assay for the analysis of fentanyl analogs in urine Mario Enrique Alburges
  4. ↑ Chen ZR, Irvine RJ, Somogyi AA, Bochner F (1991). "Mu receptor binding of some commonly used opioids and their metabolites". Life Sci. 48 (22): 2165–71. doi:10.1016/0024-3205(91)90150-a. PMID   1851921.
  5. ↑ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID   25976511.
  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.
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