ADBICA

ADBICA
Clinical data
ATC code	racemate: none;
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide;
CAS Number	racemate: 1445583-48-1 ;
PubChem CID	racemate: 72710773;
ChemSpider	racemate: 29342130;
UNII	racemate: Q71G788A6H; S isomer: P0248QCZ04 ;
CompTox Dashboard (EPA)	racemate: DTXSID801009996 ;
Chemical and physical data
Formula	C20H29N3O2
Molar mass	343.471 g·mol−1
3D model (JSmol)	racemate: Interactive image; S isomer: Interactive image;
	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;

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]

Legal Status

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

References

^ 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.
^ WO 2009/106980, Buchler IP, et al, "Indazole Derivatives", assigned to Pfizer, Inc.
^ 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.
^ "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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[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.

[1]

[2]

[3]

[4]

Clinical data

ATC code	racemate: none
Legal status
Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide
CAS Number	racemate: 1445583-48-1^Y
PubChem CID	racemate: 72710773
ChemSpider	racemate: 29342130
UNII	racemate: Q71G788A6H S isomer: P0248QCZ04^Y
CompTox Dashboard (EPA)	racemate: DTXSID801009996
Chemical and physical data
Formula	C₂₀H₂₉N₃O₂
Molar mass	343.471 g·mol⁻¹
3D model (JSmol)	racemate: Interactive image S isomer: Interactive image
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

ADBICA

Legal Status

See also

References