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'''ADBICA''' (also known as '''ADB-PICA''') is a [[designer drug]] identified in [[synthetic cannabis]] blends in Japan in 2013.<ref>{{Cite journal | last1 = Uchiyama | first1 = N. | last2 = Matsuda | first2 = S. | last3 = Kawamura | first3 = M. | last4 = Kikura-Hanajiri | first4 = R. | last5 = Goda | first5 = Y. | title = 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 | doi = 10.1007/s11419-013-0182-9 | journal = Forensic Toxicology | year = 2013 | pmid = | pmc = }}</ref> 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 (drug)|STS-135]]. The stereochemistry of the tert-butyl side-chain in the illicitly sold 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.<ref>[http://patentscope.wipo.int/search/en/detail.jsf?docId=WO2009106980 Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980]</ref> ADBICA is a potent [[agonist]] of the [[CB1 receptor|CB<sub>1</sub> receptor]] and [[CB2 receptor|CB<sub>2</sub> receptor]] with a EC<sub>50</sub> value of 0.69 nM and 1.8 nM respectively.<ref>{{cite journal | url=http://pubs.acs.org/doi/abs/10.1021/acschemneuro.5b00112 | title=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 | author=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 | journal=ACS Chemical Neuroscience |date=July 2015 | doi=10.1021/acschemneuro.5b00112 | pmid=26134475}}</ref>
'''ADBICA''' (also known as '''ADB-PICA''') is a [[designer drug]] identified in [[synthetic cannabis]] blends in Japan in 2013.<ref>{{Cite journal | last1 = Uchiyama | first1 = N. | last2 = Matsuda | first2 = S. | last3 = Kawamura | first3 = M. | last4 = Kikura-Hanajiri | first4 = R. | last5 = Goda | first5 = Y. | title = 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 | doi = 10.1007/s11419-013-0182-9 | journal = Forensic Toxicology | year = 2013 | pmid = | pmc = }}</ref> 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 (drug)|STS-135]]. The stereochemistry of the tert-butyl side-chain in the illicitly sold 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.<ref>[http://patentscope.wipo.int/search/en/detail.jsf?docId=WO2009106980 Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980]</ref> ADBICA is a potent [[agonist]] of the [[CB1 receptor|CB<sub>1</sub> receptor]] and [[CB2 receptor|CB<sub>2</sub> receptor]] with a EC<sub>50</sub> value of 0.69 nM and 1.8 nM respectively.<ref>{{cite journal | url=http://pubs.acs.org/doi/abs/10.1021/acschemneuro.5b00112 | title=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 | author=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 | journal=ACS Chemical Neuroscience |date=July 2015 | doi=10.1021/acschemneuro.5b00112 | pmid=26134475}}</ref>

==Legal Status==

As of October 2015 ADBICA is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | accessdate=1 October 2015}}</ref>


==See also==
==See also==

Revision as of 22:29, 30 September 2015

ADBICA
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide
CAS Number
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H29N3O2
Molar mass343.46 g/mol g·mol−1
3D model (JSmol)
  • CCCCCN1C=C(C2=CC=CC=C21)C(=O)NC(C(=O)N)C(C)(C)C
  • 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 illicitly sold 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 a EC50 value of 0.69 nM and 1.8 nM respectively.[3]

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. doi:10.1007/s11419-013-0182-9.
  2. ^ Buchler IP et al, INDAZOLE DERIVATIVES. WO 2009/106980
  3. ^ 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)
  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. Retrieved 1 October 2015.


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