4-Fluoroisobutyrfentanyl

Last updated
4-Fluoroisobutyrfentanyl
4-Fluoroisobutyrfentanyl.svg
Legal status
Legal status
Identifiers
  • N-(4-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-isobutanamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C23H29FN2O
Molar mass 368.496 g·mol−1
3D model (JSmol)
  • CC(C)C(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F
  • InChI=1S/C23H29FN2O/c1-18(2)23(27)26(21-10-8-20(24)9-11-21)22-13-16-25(17-14-22)15-12-19-6-4-3-5-7-19/h3-11,18,22H,12-17H2,1-2H3
  • Key:OZDOSQNUJIXEOR-UHFFFAOYSA-N

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. [1] [2] [3] [4] [5] It is closely related to 4-fluorofentanyl, which has an EC50 value of 4.2 nM for the human μ-opioid receptor. [6] 4-fluoroisobutyrylfentanyl is a highly selective μ-opioid receptor agonist whose analgesic potency is almost ten times of that reported for morphine. [7]

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. [8]

Legality

4-Fluoroisobutyrylfentanyl is a Schedule I controlled substance in the United States. [9] In the UK, it is a Class A drug. In Canada, it is a Schedule I drug.

See also

Related Research Articles

Carfentanil Chemical compound

Carfentanil or carfentanyl, sold under the brand name Wildnil, is an opioid analgesic which is used in veterinary medicine to anesthetize large animals such as elephants and bears. It is typically administered in this context by tranquilizer dart. Carfentanil has also been used in humans for imaging of opioid receptors. It has additionally been encountered as an illicit drug, typically used by injection, insufflation, or inhalation. Deaths have been reported in association with carfentanil.

3-Methylfentanyl Opioid analgesic

3-Methylfentanyl is an opioid analgesic that is an analog of fentanyl. 3-Methylfentanyl is one of the most potent opioids, estimated to be between 400 and 6000 times stronger than morphine, depending on which isomer is used.

Parafluorofentanyl Opioid analgesic

Parafluorofentanyl is an opioid analgesic analogue of fentanyl developed by Janssen Pharmaceutica in the 1960s.

3-Methylthiofentanyl Opioid analgesic

3-Methyl-thiofentanyl is an opioid analgesic and analogue of fentanyl.

3-Allylfentanyl Opioid analgesic

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

Phenaridine 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.

Mirfentanil Chemical compound

Mirfentanil is a fentanyl derivative with strong selectivity for the μ opioid receptor. At lower doses, it antagonizes the analgesic effects of alfentanil and substitutes for naloxone in morphine-treated monkeys; however, it also reverses naloxone-precipitated withdrawal in pigeons trained to discriminate morphine from naloxone.

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.

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.

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) 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.

4-Methoxybutyrfentanyl Opioid analgesic

4-Methoxybutyrfentanyl is an opioid analgesic that is an analog of butyrfentanyl and has been sold online as a designer drug.

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.

Isobutyrylfentanyl 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.

References

  1. ↑ "FIBF". Cayman Chemical.
  2. ↑ Watanabe S, Vikingsson S, Roman M, Green H, Kronstrand R, Wohlfarth A (July 2017). "In Vitro and In Vivo Metabolite Identification Studies for the New Synthetic Opioids Acetylfentanyl, Acrylfentanyl, Furanylfentanyl, and 4-Fluoro-Isobutyrylfentanyl". The AAPS Journal. 19 (4): 1102–1122. doi:10.1208/s12248-017-0070-z. PMID   28382544. S2CID   207056734.
  3. ↑ Helander A, Bäckberg M, Signell P, Beck O (July 2017). "Intoxications involving acrylfentanyl and other novel designer fentanyls - results from the Swedish STRIDA project". Clinical Toxicology. 55 (6): 589–599. doi:10.1080/15563650.2017.1303141. PMID   28349714. S2CID   11978059.
  4. ↑ Strayer KE, Antonides HM, Juhascik MP, Daniulaityte R, Sizemore IE (January 2018). "-1 Concentrations". ACS Omega. 3 (1): 514–523. doi:10.1021/acsomega.7b01536. PMC   5793031 . PMID   29399650.
  5. ↑ Pardi J, Toriello A, Cooper G (January 2020). "Evaluation of 4-fluoroisobutyrylfentanyl in blood samples from 247 authentic cases submitted to the New York City Office of Chief Medical Examiner in 2017–2018". Forensic Toxicology. 38 (2): 340–351. doi:10.1007/s11419-019-00518-6. ISSN   1860-8973. S2CID   210135027.
  6. ↑ Ulens C, Van Boven M, Daenens P, Tytgat J (September 2000). "Interaction of p-fluorofentanyl on cloned human opioid receptors and exploration of the role of Trp-318 and His-319 in mu-opioid receptor selectivity". The Journal of Pharmacology and Experimental Therapeutics. 294 (3): 1024–33. PMID   10945855.
  7. ↑ "4F-iBF risk assessment" (PDF). EMCDDA.
  8. ↑ 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.
  9. ↑ "Controlled Substances by DEA Drug Code Number" (PDF). Drug Enforcement Administration.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.