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ADBICA

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

  • Sisomer: CCCCCN1C=C(C2=CC=CC=C21)C(=O)N[C@H](C(=O)N)C(C)(C)C
  • 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

ADBICA(also known asADB-PICA) is adesigner drugidentified insynthetic cannabisblends 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, likeSDB-001andSTS-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 potentagonistof theCB1receptorandCB2receptorwith an EC50value of 0.69 nM and 1.8 nM respectively.[3]

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As of October 2015 ADBICA is a controlled substance in China.[4]

See also

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References

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  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.S2CID1279637.
  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.PMID26134475.
  4. ^"Về in và phát hành 《 phi dược dùng loại gây tê dược phẩm cùng tinh thần dược phẩm liệt quản biện pháp 》 thông tri"(in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe originalon 1 October 2015.Retrieved1 October2015.