FUB-APINACA

FUB-APINACA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name N-(Adamantan-1-yl)-1-[(4-fluorophenyl)methyl]-1H-indazole-3-carboxamide;
CAS Number	2180933-90-6 ;
PubChem CID	118796517;
ChemSpider	30922497;
UNII	OF9Q7PH4UD;
CompTox Dashboard (EPA)	DTXSID101336146 ;
Chemical and physical data
Formula	C25H26FN3O
Molar mass	403.501 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(NC1(C[C@H]2C3)C[C@H]3C[C@H](C2)C1)C4=NN(CC5=CC=C(F)C=C5)C6=C4C=CC=C6;
	InChI InChI=1S/C25H26FN3O/c26-20-7-5-16(6-8-20)15-29-22-4-2-1-3-21(22)23(28-29)24(30)27-25-12-17-9-18(13-25)11-19(10-17)14-25/h1-8,17-19H,9-15H2,(H,27,30)/t17-,18+,19-,25?; Key:MWBHSNBPUSKVDD-LPSAYFBNSA-N;

FUB-APINACA (also known as A-FUBINACA according to the EMCCDA framework for naming synthetic cannabinoids^[1] and FUB-AKB48) is an indazole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB₁ receptor and has been sold online as a designer drug.^[2] It is an analog of APINACA and 5F-APINACA where the pentyl chain has been replaced with fluorobenzyl.

Pharmacology

FUB-APINACA acts as a full agonist with a binding affinity of 1.06 nM at CB₁ and 0.174 nM at CB₂ cannabinoid receptors.^[3]

Legal status

In the United States, FUB-APINACA was temporarily emergency scheduled by the DEA in 2019.^[4] and made a permanent Schedule I Controlled Substance nationwide on April 7, 2022.^[5] Previously, it was illegal only in Alabama (listed as FUB-AKB48).^[6]

Sweden's public health agency suggested classifying FUB-APINACA as a hazardous substance on November 10, 2014.^[7]

References

^ Pulver B, Fischmann S, Gallegos A, Christie R. EMCDDA framework and practical guidance for naming synthetic cannabinoids. Drug Test Anal. 2023;15(3): 255‐276. doi:10.1002/dta.3403
^ "FUB-AKB48". Cayman Chemical. Retrieved 23 July 2015.
^ Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.
^ "Schedules of Controlled Substances: Temporary Placement of 5F-EDMB-PINACA, 5F-MDMB-PICA, FUB-AKB48, 5F-CUMYL-PINACA, and FUB-144 into Schedule I". Federal Register. 2019-04-16.
^ "Schedules of Controlled Substances: Placement of 5F-EDMB-PINACA, 5FMDMB-PICA, FUB-AKB48, 5F-CUMYLPINACA, and FUB-144 in Schedule I" (PDF). Federal Register. 87 (67). 7 April 2022.
^ Alabama Senate Bill SB 333: Controlled Substances
^ "Cannabinoider föreslås bli klassade som hälsofarlig vara". Folkhälsomyndigheten. Retrieved 23 July 2015.

[1] Pulver B, Fischmann S, Gallegos A, Christie R. EMCDDA framework and practical guidance for naming synthetic cannabinoids. Drug Test Anal. 2023;15(3): 255‐276. doi:10.1002/dta.3403

[2] "FUB-AKB48". Cayman Chemical. Retrieved 23 July 2015.

[3] Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.

[fedreg-Apr-2019-4] "Schedules of Controlled Substances: Temporary Placement of 5F-EDMB-PINACA, 5F-MDMB-PICA, FUB-AKB48, 5F-CUMYL-PINACA, and FUB-144 into Schedule I". Federal Register. 2019-04-16.

[5] "Schedules of Controlled Substances: Placement of 5F-EDMB-PINACA, 5FMDMB-PICA, FUB-AKB48, 5F-CUMYLPINACA, and FUB-144 in Schedule I" (PDF). Federal Register. 87 (67). 7 April 2022.

[6] Alabama Senate Bill SB 333: Controlled Substances

[7] "Cannabinoider föreslås bli klassade som hälsofarlig vara". Folkhälsomyndigheten. Retrieved 23 July 2015.

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FUB-APINACA

Contents

Pharmacology

Legal status

See also

References

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B US: Schedule I
Identifiers
IUPAC name N-(Adamantan-1-yl)-1-[(4-fluorophenyl)methyl]-1H-indazole-3-carboxamide
CAS Number	2180933-90-6^Y
PubChem CID	118796517
ChemSpider	30922497
UNII	OF9Q7PH4UD
CompTox Dashboard (EPA)	DTXSID101336146
Chemical and physical data
Formula	C₂₅H₂₆FN₃O
Molar mass	403.501 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(NC1(C[C@H]2C3)C[C@H]3C[C@H](C2)C1)C4=NN(CC5=CC=C(F)C=C5)C6=C4C=CC=C6
InChI InChI=1S/C25H26FN3O/c26-20-7-5-16(6-8-20)15-29-22-4-2-1-3-21(22)23(28-29)24(30)27-25-12-17-9-18(13-25)11-19(10-17)14-25/h1-8,17-19H,9-15H2,(H,27,30)/t17-,18+,19-,25? Key:MWBHSNBPUSKVDD-LPSAYFBNSA-N