Aza-THIP

Aza-THIP
Clinical data
Other names	Azagaboxadol
Drug class	GABAA-ρ antagonist
ATC code	None;
Identifiers
	IUPAC name 1,2,4,5,6,7-hexahydropyrazolo[3,4-c]pyridin-3-one;
CAS Number	654666-65-6;
PubChem CID	55285412;
ChemSpider	27267416;
CompTox Dashboard (EPA)	DTXSID20717441 ;
Chemical and physical data
Formula	C6H9N3O
Molar mass	139.158 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CNCC2=C1C(=O)NN2;
	InChI InChI=1S/C6H9N3O/c10-6-4-1-2-7-3-5(4)8-9-6/h7H,1-3H2,(H2,8,9,10); Key:UPMMUUFLHUEUKP-UHFFFAOYSA-N;

Aza-THIP is a selective and moderately potent GABA_A-ρ (GABA_C receptor) antagonist related to gaboxadol (THIP).^[1]^[2]^[3]^[4] Unlike gaboxadol, it is virtually inactive at the GABA_A receptor.^[1]^[2]^[4]^[5] The drug was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1979.^[6]^[7]

References

^ ^a ^b Krogsgaard-Larsen P, Frølund B, Liljefors T (2006). "GABAA Agonists and Partial Agonists: THIP (Gaboxadol) as a Non-Opioid Analgesic and a Novel Type of Hypnotic1". GABA(A) agonists and partial agonists: THIP (Gaboxadol) as a non-opioid analgesic and a novel type of hypnotic. Advances in Pharmacology. Vol. 54. pp. 53–71. doi:10.1016/s1054-3589(06)54003-7. ISBN 978-0-12-032957-1. PMID 17175810.
^ ^a ^b Johnston GA, Chebib M, Hanrahan JR, Mewett KN (August 2003). "GABA(C) receptors as drug targets". Current Drug Targets. CNS and Neurological Disorders. 2 (4): 260–268. doi:10.2174/1568007033482805. PMID 12871036.
^ Johnston GA, Chebib M, Hanrahan JR, Mewett KN (December 2010). "Neurochemicals for the investigation of GABA(C) receptors". Neurochemical Research. 35 (12): 1970–1977. doi:10.1007/s11064-010-0271-7. PMID 20963487.
^ ^a ^b Krehan D, Frølund B, Ebert B, Nielsen B, Krogsgaard-Larsen P, Johnston GA, et al. (November 2003). "Aza-THIP and related analogues of THIP as GABA C antagonists". Bioorganic & Medicinal Chemistry. 11 (23): 4891–4896. doi:10.1016/j.bmc.2003.09.016. PMID 14604650.
^ Frølund B, Ebert B, Kristiansen U, Liljefors T, Krogsgaard-Larsen P (August 2002). "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry. 2 (8): 817–832. doi:10.2174/1568026023393525. PMID 12171573.
^ Krogsgaard-Larsen P, Falch E (August 1981). "GABA agonists. Development and interactions with the GABA receptor complex". Molecular and Cellular Biochemistry. 38 Spec No (Pt 1): 129–146. doi:10.1007/BF00235692. PMID 6270544.
^ Krogsgaard-Larsen P, Roldskov-Christiansen T (1979). "GABA agonists. Synthesis and structure-activity studies on analogs of isoguvacine and THIP". Chimica Therapeutica (European Journal of Medicinal Chemistry). 14: 157–164.

[KrogsgaardLarsen_2006-1] Krogsgaard-Larsen P, Frølund B, Liljefors T (2006). "GABAA Agonists and Partial Agonists: THIP (Gaboxadol) as a Non-Opioid Analgesic and a Novel Type of Hypnotic1". GABA(A) agonists and partial agonists: THIP (Gaboxadol) as a non-opioid analgesic and a novel type of hypnotic. Advances in Pharmacology. Vol. 54. pp. 53–71. doi:10.1016/s1054-3589(06)54003-7. ISBN 978-0-12-032957-1. PMID 17175810.

[Johnston_2003-2] Johnston GA, Chebib M, Hanrahan JR, Mewett KN (August 2003). "GABA(C) receptors as drug targets". Current Drug Targets. CNS and Neurological Disorders. 2 (4): 260–268. doi:10.2174/1568007033482805. PMID 12871036.

[Johnston_2010-3] Johnston GA, Chebib M, Hanrahan JR, Mewett KN (December 2010). "Neurochemicals for the investigation of GABA(C) receptors". Neurochemical Research. 35 (12): 1970–1977. doi:10.1007/s11064-010-0271-7. PMID 20963487.

[Krehan_2003-4] Krehan D, Frølund B, Ebert B, Nielsen B, Krogsgaard-Larsen P, Johnston GA, et al. (November 2003). "Aza-THIP and related analogues of THIP as GABA C antagonists". Bioorganic & Medicinal Chemistry. 11 (23): 4891–4896. doi:10.1016/j.bmc.2003.09.016. PMID 14604650.

[Frlund_2002-5] Frølund B, Ebert B, Kristiansen U, Liljefors T, Krogsgaard-Larsen P (August 2002). "GABA(A) receptor ligands and their therapeutic potentials". Current Topics in Medicinal Chemistry. 2 (8): 817–832. doi:10.2174/1568026023393525. PMID 12171573.

[KrogsgaardLarsen_1981-6] Krogsgaard-Larsen P, Falch E (August 1981). "GABA agonists. Development and interactions with the GABA receptor complex". Molecular and Cellular Biochemistry. 38 Spec No (Pt 1): 129–146. doi:10.1007/BF00235692. PMID 6270544.

[citefb42a462-7] Krogsgaard-Larsen P, Roldskov-Christiansen T (1979). "GABA agonists. Synthesis and structure-activity studies on analogs of isoguvacine and THIP". Chimica Therapeutica (European Journal of Medicinal Chemistry). 14: 157–164.

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See also

References