Quinpirole

Quinpirole
Names
	Preferred IUPAC name (4aR,8aR)-5-Propyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrazolo[3,4-g]quinoline
Identifiers
CAS Number	80373-22-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75401 ;
ChEMBL	ChEMBL240773 ;
ChemSpider	49279 ;
IUPHAR/BPS	2;
MeSH	D019257
PubChem CID	54562;
UNII	20OP60125T ;
CompTox Dashboard (EPA)	DTXSID9048229 ;
	InChI InChI=1S/C13H21N3/c1-2-5-16-6-3-4-10-7-12-11(8-13(10)16)9-14-15-12/h9-10,13H,2-8H2,1H3,(H,14,15)/t10-,13-/m1/s1 Key: FTSUPYGMFAPCFZ-ZWNOBZJWSA-N ; InChI=1/C13H21N3/c1-2-5-16-6-3-4-10-7-12-11(8-13(10)16)9-14-15-12/h9-10,13H,2-8H2,1H3,(H,14,15)/t10-,13-/m1/s1 Key: FTSUPYGMFAPCFZ-ZWNOBZJWBQ;
	SMILES CCCN1CCC[C@H]2[C@H]1CC3=C(C2)NN=C3;
Properties
Chemical formula	C13H21N3
Molar mass	219.33 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Quinpirole is a psychoactive drug and research chemical which acts as a selective D₂ and D₃ receptor agonist. It is used in scientific research.^[1]^[2]^[3] Quinpirole has been shown to increase locomotion and sniffing behavior in mice treated with it. At least one study has found that quinpirole induces compulsive behavior symptomatic of obsessive compulsive disorder in rats.^[4] Another study in rats show that quinpirole produces significant THC-like effects when metabolic degradation of anandamide is inhibited, supporting the hypothesis that these effects of quinpirole are mediated by cannabinoid CB₁ receptors.^[5] Quinpirole may also reduce relapse in adolescent rat models of cocaine addiction.^[6]

Experiments in flies found quinpirole may have neuroprotective effects against Parkinson's disease-like pathology.^[7] Moreover, in primary neuronal cultures it also reduces the rate of firing in dopaminergic neurons.^[7]

References

^ Eilam D, Szechtman H (February 1989). "Biphasic effect of D-2 agonist quinpirole on locomotion and movements". European Journal of Pharmacology. 161 (2–3): 151–7. doi:10.1016/0014-2999(89)90837-6. PMID 2566488.
^ Navarro JF, Maldonado E (September 1999). "Behavioral profile of quinpirole in agonistic encounters between male mice". Methods and Findings in Experimental and Clinical Pharmacology. 21 (7): 477–80. doi:10.1358/mf.1999.21.7.550110. PMID 10544391. S2CID 25978291.
^ Culm KE, Lugo-Escobar N, Hope BT, Hammer RP (October 2004). "Repeated quinpirole treatment increases cAMP-dependent protein kinase activity and CREB phosphorylation in nucleus accumbens and reverses quinpirole-induced sensorimotor gating deficits in rats". Neuropsychopharmacology. 29 (10): 1823–30. doi:10.1038/sj.npp.1300483. PMID 15138441.
^ Szechtman, Henry; Sulis, William; Eilam, David (1998). "Quinpirole induces compulsive checking behavior in rats: A potential animal model of obsessive-compulsive disorder (OCD)". Behavioral Neuroscience. 112 (6): 1475–85. doi:10.1037/0735-7044.112.6.1475. hdl:11375/26795. PMID 9926830.
^ Solinas, Marcello; Tanda, Gianluigi; Wertheim, Carrie E.; Goldberg, Steven R. (2016-10-08). "Dopaminergic augmentation of delta-9-tetrahydrocannabinol (THC) discrimination: possible involvement of D2-induced formation of anandamide". Psychopharmacology. 209 (2): 191–202. doi:10.1007/s00213-010-1789-8. ISSN 0033-3158. PMC 2834964. PMID 20179908.
^ Zbukvic, Isabel C.; Ganella, Despina E.; Perry, Christina J.; Madsen, Heather B.; Bye, Christopher R.; Lawrence, Andrew J.; Kim, Jee Hyun (2016-06-01). "Role of Dopamine 2 Receptor in Impaired Drug-Cue Extinction in Adolescent Rats". Cerebral Cortex. 26 (6): 2895–2904. doi:10.1093/cercor/bhw051. ISSN 1047-3211. PMC 4869820. PMID 26946126.
^ ^a ^b Wiemerslage L, Schultz BJ, Ganguly A, Lee D (2013). "Selective degeneration of dopaminergic neurons by MPP(+) and its rescue by D2 autoreceptors in Drosophila primary culture". J Neurochem. 126 (4): 529–40. doi:10.1111/jnc.12228. PMC 3737274. PMID 23452092.

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[pmid2566488-1] Eilam D, Szechtman H (February 1989). "Biphasic effect of D-2 agonist quinpirole on locomotion and movements". European Journal of Pharmacology. 161 (2–3): 151–7. doi:10.1016/0014-2999(89)90837-6. PMID 2566488.

[pmid10544391-2] Navarro JF, Maldonado E (September 1999). "Behavioral profile of quinpirole in agonistic encounters between male mice". Methods and Findings in Experimental and Clinical Pharmacology. 21 (7): 477–80. doi:10.1358/mf.1999.21.7.550110. PMID 10544391. S2CID 25978291.

[pmid15138441-3] Culm KE, Lugo-Escobar N, Hope BT, Hammer RP (October 2004). "Repeated quinpirole treatment increases cAMP-dependent protein kinase activity and CREB phosphorylation in nucleus accumbens and reverses quinpirole-induced sensorimotor gating deficits in rats". Neuropsychopharmacology. 29 (10): 1823–30. doi:10.1038/sj.npp.1300483. PMID 15138441.

[4] Szechtman, Henry; Sulis, William; Eilam, David (1998). "Quinpirole induces compulsive checking behavior in rats: A potential animal model of obsessive-compulsive disorder (OCD)". Behavioral Neuroscience. 112 (6): 1475–85. doi:10.1037/0735-7044.112.6.1475. hdl:11375/26795. PMID 9926830.

[5] Solinas, Marcello; Tanda, Gianluigi; Wertheim, Carrie E.; Goldberg, Steven R. (2016-10-08). "Dopaminergic augmentation of delta-9-tetrahydrocannabinol (THC) discrimination: possible involvement of D2-induced formation of anandamide". Psychopharmacology. 209 (2): 191–202. doi:10.1007/s00213-010-1789-8. ISSN 0033-3158. PMC 2834964. PMID 20179908.

[6] Zbukvic, Isabel C.; Ganella, Despina E.; Perry, Christina J.; Madsen, Heather B.; Bye, Christopher R.; Lawrence, Andrew J.; Kim, Jee Hyun (2016-06-01). "Role of Dopamine 2 Receptor in Impaired Drug-Cue Extinction in Adolescent Rats". Cerebral Cortex. 26 (6): 2895–2904. doi:10.1093/cercor/bhw051. ISSN 1047-3211. PMC 4869820. PMID 26946126.

[pmid23452092-7] Wiemerslage L, Schultz BJ, Ganguly A, Lee D (2013). "Selective degeneration of dopaminergic neurons by MPP(+) and its rescue by D2 autoreceptors in Drosophila primary culture". J Neurochem. 126 (4): 529–40. doi:10.1111/jnc.12228. PMC 3737274. PMID 23452092.

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See also

References