ADBICA

ADBICA (also known as ADB-PICA) is a designer drug identified in synthetic cannabis blends in Japan in 2013.[1] ADBICA had not previously been reported in the scientific literature prior to its sale as a component of synthetic cannabis blends. ADBICA features a carboxamide group at the 3-indole position, like SDB-001 and STS-135. The stereochemistry of the tert-butyl side-chain in the product is unresolved, though in a large series of indazole derivatives structurally similar to ADBICA that are disclosed in Pfizer patent WO 2009/106980, activity resides exclusively in the (S) enantiomers.[2] ADBICA is a potent agonist of the CB1 receptor and CB2 receptor with an EC50 value of 0.69 nM and 1.8 nM respectively.[3]

ADBICA
Clinical data
ATC code
  • racemate: none
Legal status
Legal status
Identifiers
IUPAC name
  • N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H29N3O2
Molar mass343.471 g·mol−1
3D model (JSmol)
SMILES
  • racemate: CCCCCN1C=C(C2=CC=CC=C21)C(=O)NC(C(=O)N)C(C)(C)C

  • S isomer: CCCCCN1C=C(C2=CC=CC=C21)C(=O)N[C@H](C(=O)N)C(C)(C)C
InChI
  • racemate: InChI=1S/C20H29N3O2/c1-5-6-9-12-23-13-15(14-10-7-8-11-16(14)23)19(25)22-17(18(21)24)20(2,3)4/h7-8,10-11,13,17H,5-6,9,12H2,1-4H3,(H2,21,24)(H,22,25)
  • Key:IXUYMXAKKYWKRG-UHFFFAOYSA-N

As of October 2015 ADBICA is a controlled substance in China.[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 (2): 223–240. doi:10.1007/s11419-013-0182-9. S2CID 1279637.
  2. WO 2009/106980, Buchler IP, et al, "Indazole Derivatives", assigned to Pfizer, Inc.
  3. Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "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 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475.
  4. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.


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