THC Science

ADB-FUBINACA
Identifiers
	IUPAC name N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide;
CAS Number	1445583-51-6 ;
ChemSpider	29763706;
CompTox Dashboard (EPA)	DTXSID701009981 ;
Chemical and physical data
Formula	C21H23FN4O2
Molar mass	382.43 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 a potent agonist of the CB₁ receptor and CB₂ receptor with a 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. The stereochemistry of the tert-butyl side-chain in the illicitly sold product is unresolved.^{[citation needed]}

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

References

^ Template:Cite DOI
^ 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. doi:10.1021/acschemneuro.5b00112. PMID 26134475.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106982

[1] Template:Cite DOI

[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. doi:10.1021/acschemneuro.5b00112. PMID 26134475.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106982

[1]

[2]

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Identifiers

IUPAC name N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide
CAS Number	1445583-51-6^Y
ChemSpider	29763706
CompTox Dashboard (EPA)	DTXSID701009981
Chemical and physical data
Formula	C₂₁H₂₃FN₄O₂
Molar mass	382.43 g/mol g·mol⁻¹
3D model (JSmol)	Interactive image
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