ADB-FUBINACA

ADB-FUBINACA

Systematic (IUPAC) name
N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide
Clinical data
Legal status	CA: Schedule II
Identifiers
CAS Number	1445583-51-6 Y
PubChem	CID 70969086
ChemSpider	29763706
Chemical data
Formula	C21H23FN4O2
Molar mass	382.43 g/mol
SMILES O=C(NC(C(N)=O)C(C)(C)C)C1=NN(CC2=CC=C(F)C=C2)C3=C1C=CC=C3
InChI InChI=1S/C21H23FN4O2/c1-21(2,3)18(19(23)27)24-20(28)17-15-6-4-5-7-16(15)26(25-17)12-13-8-10-14(22)11-9-13/h4-11,18H,12H2,1-3H3,(H2,23,27)(H,24,28) Key:ZSSGCSINPVBLQD-UHFFFAOYSA-N

ADB-FUBINACA is a designer drug identified in synthetic cannabis blends in Japan in 2013.^[1] The (S) enantiomer of ADB-FUBINACA is claimed in Pfizer patent WO 2009/106982 and has been reported to be a potent agonist of the CB₁ receptor and CB₂ receptor with an EC₅₀ value of 1.2 nM and 3.5 nM respectively.^[2][3] ADB-FUBINACA features a carboxamide group at the 3-indazole position, like SDB-001 and STS-135. ADB-FUBINACA appears to be the product of rational drug design, since it differs from AB-FUBINACA only by the replacement of the isopropyl group with a tert-butyl group.

An analogue of ADB-FUBINACA, ADSB-FUB-187, containing a more functionalized carboxamide substituent was recently reported.

Side effects

One death through coronary arterial thrombosis has been linked to ADB-FUBINACA intoxication.^[4]

See also

References

1. ↑ Uchiyama, N.; Matsuda, S.; Kawamura, M.; Kikura-Hanajiri, R.; Goda, Y. (2013). "Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products". Forensic Toxicology 31: 223–240. doi:10.1007/s11419-013-0182-9. 
2. ↑ Samuel D Banister, Michael Moir, Jordyn Stuart, Richard C Kevin, Katie E Wood, Mitchell Longworth, Shane M Wilkinson, Corinne Beinat, Alxendra S Buchanan, Michelle Glass, Mark Connor, Iain S McGregor, Michael Kassiou (July 2015). "The pharmacology of indole and indazole synthetic cannabinoid designer drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA and 5F-ADBICA". ACS Chemical Neuroscience 6: 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475. 
3. ↑ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106982
4. ↑ Kevin G. Shanks, William Clark, George Behonick (January 2016). "Death Associated With the Use of the Synthetic Cannabinoid ADB-FUBINACA". Journal of Analytical Toxicology. doi:10.1093/jat/bkv142. PMID 26755539.