ADB-FUBINACA

Chemical compound From Wikipedia, the free encyclopedia

ADB-FUBINACA (ADMB-FUBINACA[2]) is a designer drug identified in synthetic cannabis blends in Japan in 2013.[3][4] In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration.[5]

Legal status
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ADB-FUBINACA
Legal status
Legal status
Identifiers
  • N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H23FN4O2
Molar mass382.439 g·mol−1
3D model (JSmol)
  • 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)/t18-/m1/s1
  • Key:ZSSGCSINPVBLQD-GOSISDBHSA-N
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The name is an acronym for N-(1-Amino-3,3-Dimethyl-1-oxoButan-2-yl)-1-(4-FlUoroBenzyl)-1H-INdAzole-3-CarboxAmide.

The (S)-enantiomer of ADB-FUBINACA is described in a 2009 Pfizer patent[6] and has been reported to be a potent agonist of the CB1 receptor and the CB2 receptor with EC50 values of 1.2 nM and 3.5 nM, respectively.[6][7] 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.[8]

Metabolism

Twenty-three ADB-FUBINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Major metabolic pathways were alkyl and indazole hydroxylation, terminal amide hydrolysis, subsequent glucuronide conjugations, and dehydrogenation.[9]

Legality

In the United States, ADB-FUBINACA is a Schedule I controlled substance.[10]

See also

References

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