Furanylfentanyl information

Furanylfentanyl
Clinical data
ATC code	none;
Legal status
Legal status	BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Under Psychoactive Substances Act; US: Schedule I; UN: Narcotic Schedule I; Illegal in Sweden;
Identifiers
	IUPAC name N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide;
CAS Number	101345-66-8;
PubChem CID	13653606;
ChemSpider	14921702;
UNII	3F7C9J1LS7;
KEGG	C22761;
Chemical and physical data
Formula	C24H26N2O2
Molar mass	374.484 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N(C1CCN(CC1)CCc2ccccc2)c3ccccc3)c4occc4;
	InChI InChI=1/C24H26N2O2/c27-24(23-12-7-19-28-23)26(21-10-5-2-6-11-21)22-14-17-25(18-15-22)16-13-20-8-3-1-4-9-20/h1-12,19,22H,13-18H2; Key:FZJVHWISUGFFQV-UHFFFAOYSA-N;

Furanylfentanyl (Fu-F) is an opioid analgesic that is an analog of fentanyl^[1] and has been sold as a designer drug.^[2]^[3] It has an ED₅₀ value of 0.02 mg/kg in mice.^[4] This makes it approximately one fifth as potent as fentanyl.^[5]

^ Bagley JR, Wynn RL, Rudo FG, Doorley BM, Spencer HK, Spaulding T (March 1989). "New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry. 32 (3): 663–671. doi:10.1021/jm00123a028. PMID 2563773.
^ Kanamori T, Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Togawa-Iwata Y (August 2020). "Detection and confirmation of the ring-opened carboxylic acid metabolite of a new synthetic opioid furanylfentanyl". Forensic Toxicology. 39: 114–122. doi:10.1007/s11419-020-00546-7. ISSN 1860-8973.
^ Bilel S, Azevedo Neto J, Arfè R, Tirri M, Gaudio RM, Fantinati A, et al. (May 2022). "In vitro and in vivo pharmaco-dynamic study of the novel fentanyl derivatives: Acrylfentanyl, Ocfentanyl and Furanylfentanyl". Neuropharmacology. 209: 109020. doi:10.1016/j.neuropharm.2022.109020. PMID 35247453. S2CID 247172069.
^ Huang BS, Terrell RC, Deutsche KH, Kudzma LV, Lalinde NL (9 April 1984). "Patent US4584303 - N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds". The Boc Group, Inc.
^ Chen Q, Shang Y, Xu Y, Li P, Li P, Liu GL (February 2016). "Analgesic effect and pharmacological mechanism of fentanyl and butorphanol in a rat model of incisional pain". Journal of Clinical Anesthesia. 28: 67–73. doi:10.1016/j.jclinane.2015.08.010. PMID 26440441.

[1] Bagley JR, Wynn RL, Rudo FG, Doorley BM, Spencer HK, Spaulding T (March 1989). "New 4-(heteroanilido)piperidines, structurally related to the pure opioid agonist fentanyl, with agonist and/or antagonist properties". Journal of Medicinal Chemistry. 32 (3): 663–671. doi:10.1021/jm00123a028. PMID 2563773.

[2] Kanamori T, Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Togawa-Iwata Y (August 2020). "Detection and confirmation of the ring-opened carboxylic acid metabolite of a new synthetic opioid furanylfentanyl". Forensic Toxicology. 39: 114–122. doi:10.1007/s11419-020-00546-7. ISSN 1860-8973.

[3] Bilel S, Azevedo Neto J, Arfè R, Tirri M, Gaudio RM, Fantinati A, et al. (May 2022). "In vitro and in vivo pharmaco-dynamic study of the novel fentanyl derivatives: Acrylfentanyl, Ocfentanyl and Furanylfentanyl". Neuropharmacology. 209: 109020. doi:10.1016/j.neuropharm.2022.109020. PMID 35247453. S2CID 247172069.

[4] Huang BS, Terrell RC, Deutsche KH, Kudzma LV, Lalinde NL (9 April 1984). "Patent US4584303 - N-aryl-N-(4-piperidinyl)amides and pharmaceutical compositions and method employing such compounds". The Boc Group, Inc.

[5] Chen Q, Shang Y, Xu Y, Li P, Li P, Liu GL (February 2016). "Analgesic effect and pharmacological mechanism of fentanyl and butorphanol in a rat model of incisional pain". Journal of Clinical Anesthesia. 28: 67–73. doi:10.1016/j.jclinane.2015.08.010. PMID 26440441.

Furanylfentanyl information

and 24 Related for: Furanylfentanyl information

Furanylfentanyl

Parafluorofentanyl

Furanyl norfentanyl

Brazilian Controlled Drugs and Substances Act

Ketamine

Norfentanyl

Naloxone

Acetylfentanyl

Tetrahydrocannabinol

Fentanyl

Acrylfentanyl

Oxycodone

Phencyclidine

Cannabidiol

Mitragyna speciosa

C24H26N2O2

Kava

Dextromethorphan

Menthol

Buprenorphine

Methadone

Opium

Desomorphine

Loperamide

Clinical data


ATC code	none
Legal status
Legal status	BR: Class F1 (Prohibited narcotics) CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Under Psychoactive Substances Act US: Schedule I UN: Narcotic Schedule I Illegal in Sweden
Identifiers
IUPAC name N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide
CAS Number	101345-66-8
PubChem CID	13653606
ChemSpider	14921702
UNII	3F7C9J1LS7
KEGG	C22761
Chemical and physical data
Formula	C₂₄H₂₆N₂O₂
Molar mass	374.484 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N(C1CCN(CC1)CCc2ccccc2)c3ccccc3)c4occc4
InChI InChI=1/C24H26N2O2/c27-24(23-12-7-19-28-23)26(21-10-5-2-6-11-21)22-14-17-25(18-15-22)16-13-20-8-3-1-4-9-20/h1-12,19,22H,13-18H2 Key:FZJVHWISUGFFQV-UHFFFAOYSA-N