4-Fluorobutyrfentanyl

4-Fluorobutyrfentanyl
Legal status
Legal status	CA: Schedule I; UK: Class A; US: Not FDA approved; unscheduled; Illegal in China and Sweden;
Identifiers
	IUPAC name N-(4-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-butanamide;
CAS Number	244195-31-1;
PubChem CID	86280430;
ChemSpider	32779976;
UNII	2378L0E82T;
CompTox Dashboard (EPA)	DTXSID101032566 ;
Chemical and physical data
Formula	C23H29FN2O
Molar mass	368.487563 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=C(C=C3)F;
	InChI InChI=1S/C23H29FN2O/c1-2-6-23(27)26(21-11-9-20(24)10-12-21)22-14-17-25(18-15-22)16-13-19-7-4-3-5-8-19/h3-5,7-12,22H,2,6,13-18H2,1H3; Key:QZFMCYUBPSLOBP-UHFFFAOYSA-N;

4-Fluorobutyrfentanyl (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.^[1]^[2] It is closely related to 4-fluorofentanyl, which has an EC₅₀ value of 4.2 nM for the human μ-opioid receptor.^[3]

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]

Legal status

Sweden's public health agency suggested classifying 4-fluorobutyrfentanyl as hazardous substance on August 18, 2014.^[5]

In October 2015, 4-fluorobutyrfentanyl became a controlled substance in China.^[6]

References

^ "para-Fluorobutyrylfentanyl". Cayman Chemical. Retrieved 15 July 2015.
^ Bäckberg, Matilda; Beck, Olof; Jönsson, Karl-Henrik; Helander, Anders (9 August 2015). "Opioid intoxications involving butyrfentanyl, 4-fluorobutyrfentanyl, and fentanyl from the Swedish STRIDA project". Clinical Toxicology. 53 (7): 609–617. doi:10.3109/15563650.2015.1054505. ISSN 1556-3650. PMID 26083809.
^ Ulens, Chris; Boven, Maurits Van; Daenens, Paul; Tytgat, Jan (1 September 2000). "Interaction of p-Fluorofentanyl on Cloned Human Opioid Receptors and Exploration of the Role of Trp-318 and His-319 in μ-Opioid Receptor Selectivity". Journal of Pharmacology and Experimental Therapeutics. 294 (3): 1024–1033. ISSN 1521-0103. PMID 10945855.
^ Mounteney, Jane; Giraudon, Isabelle; Denissov, Gleb; Griffiths, Paul (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.
^ "Nya substanser klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 August 2015. Retrieved 21 August 2015.
^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.

[1] "para-Fluorobutyrylfentanyl". Cayman Chemical. Retrieved 15 July 2015.

[2] Bäckberg, Matilda; Beck, Olof; Jönsson, Karl-Henrik; Helander, Anders (9 August 2015). "Opioid intoxications involving butyrfentanyl, 4-fluorobutyrfentanyl, and fentanyl from the Swedish STRIDA project". Clinical Toxicology. 53 (7): 609–617. doi:10.3109/15563650.2015.1054505. ISSN 1556-3650. PMID 26083809.

[3] Ulens, Chris; Boven, Maurits Van; Daenens, Paul; Tytgat, Jan (1 September 2000). "Interaction of p-Fluorofentanyl on Cloned Human Opioid Receptors and Exploration of the Role of Trp-318 and His-319 in μ-Opioid Receptor Selectivity". Journal of Pharmacology and Experimental Therapeutics. 294 (3): 1024–1033. ISSN 1521-0103. PMID 10945855.

[4] Mounteney, Jane; Giraudon, Isabelle; Denissov, Gleb; Griffiths, Paul (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] "Nya substanser klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 August 2015. Retrieved 21 August 2015.

[6] "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.

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Side effects

Legal status

See also

References