Isobutyrylfentanyl

Last updated
Isobutyrylfentanyl
Isobutyrylfentanyl Structure.svg
Isobutyrylfentanyl 3D BS.png
Legal status
Legal status
Identifiers
  • 2-methyl-N-phenyl-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]propanamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C23H30N2O
Molar mass 350.506 g·mol−1
3D model (JSmol)
  • CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
  • InChI=1S/C23H30N2O/c1-19(2)23(26)25(21-11-7-4-8-12-21)22-14-17-24(18-15-22)16-13-20-9-5-3-6-10-20/h3-12,19,22H,13-18H2,1-2H3
  • Key:WRPFPNIHTOSMKU-UHFFFAOYSA-N

Isobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. [1] It is believed to be around the same potency as butyrfentanyl [2] 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. [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]

Isobutyrylfentanyl is a Schedule I controlled drug in the USA since 1 February 2018. [6]

See also

Related Research Articles

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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.

Furanylfentanyl Opioid analgesic

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3-Methylbutyrfentanyl Opioid analgesic

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

4-Fluorobutyrfentanyl Opioid analgesic

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4-Methoxybutyrfentanyl Opioid analgesic

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Acrylfentanyl Opioid analgesic

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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

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Cyclopentylfentanyl Opioid analgesic

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4-Fluoroisobutyrfentanyl Chemical compound

4-Fluoroisobutyrylfentanyl (also known as 4-FIBF and p-FIBF) is an opioid analgesic that is an analog of butyrfentanyl and structural isomer of 4-Fluorobutyrfentanyl 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. 4-fluoroisobutyrylfentanyl is a highly selective μ-opioid receptor agonist whose analgesic potency is almost ten times of that reported for morphine.

Valerylfentanyl Opioid analgesic

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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.

Benzoylfentanyl 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.

Tetramethylcyclopropylfentanyl Opioid analgesic

Tetramethylcyclopropylfentanyl 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. ↑ Giorgetti, Arianna; Centola, Carmela; Giorgetti, Raffaele (2017). "Fentanyl novel derivative-related deaths". Human Psychopharmacology: Clinical and Experimental. 32 (3): e2605. doi: 10.1002/hup.2605 . ISSN   0885-6222. PMID   28635020.
  2. ↑ Higashikawa, Yoshiyasu; Suzuki, Shinichi (2008). "Studies on 1-(2-phenethyl)-4-(N-propionylanilino)piperidine (fentanyl) and its related compounds. VI. Structure-analgesic activity relationship for fentanyl, methyl-substituted fentanyls and other analogues". Forensic Toxicology. 26 (1): 1–5. doi:10.1007/s11419-007-0039-1. ISSN   1860-8965. S2CID   22092512.
  3. ↑ Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA
  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" (PDF). Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID   29042317. S2CID   21404877.
  6. ↑ "Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I". Federal Register. 1 February 2018.
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