Quinpirole

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 396961061

| ImageFile = Quinpirole.png

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| PIN = (4aR,8aR)-5-Propyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrazolo[3,4-g]quinoline

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 80373-22-4

| PubChem = 54562

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 75401

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 240773

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 20OP60125T

| IUPHAR_ligand = 2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 49279

| SMILES = CCCN1CCC[C@H]2[C@H]1CC3=C(C2)NN=C3

| 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

| InChIKey = FTSUPYGMFAPCFZ-ZWNOBZJWBQ

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = FTSUPYGMFAPCFZ-ZWNOBZJWSA-N

| RTECS =

| MeSHName = D019257}}

| Section2 = {{Chembox Properties

| Formula =

| C=13 | H=21 | N=3

| MolarMass = 219.33 g/mol

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| Section3 = {{Chembox Hazards

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Quinpirole is a psychoactive drug and research chemical which acts as a selective D₂ and D₃ receptor agonist. It is used in scientific research.{{cite journal |vauthors=Eilam D, Szechtman H |title=Biphasic effect of D-2 agonist quinpirole on locomotion and movements |journal=European Journal of Pharmacology |volume=161 |issue=2–3 |pages=151–7 |date=February 1989 |pmid=2566488 |doi= 10.1016/0014-2999(89)90837-6}}{{cite journal |vauthors=Navarro JF, Maldonado E |title=Behavioral profile of quinpirole in agonistic encounters between male mice |journal=Methods and Findings in Experimental and Clinical Pharmacology |volume=21 |issue=7 |pages=477–80 |date=September 1999 |doi=10.1358/mf.1999.21.7.550110 |pmid=10544391 |s2cid=25978291 }}{{cite journal |vauthors=Culm KE, Lugo-Escobar N, Hope BT, Hammer RP |title=Repeated quinpirole treatment increases cAMP-dependent protein kinase activity and CREB phosphorylation in nucleus accumbens and reverses quinpirole-induced sensorimotor gating deficits in rats |journal=Neuropsychopharmacology |volume=29 |issue=10 |pages=1823–30 |date=October 2004 |pmid=15138441 |doi=10.1038/sj.npp.1300483 |doi-access=free }} 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.{{cite journal|doi=10.1037/0735-7044.112.6.1475|title=Quinpirole induces compulsive checking behavior in rats: A potential animal model of obsessive-compulsive disorder (OCD)|year=1998|last1=Szechtman|first1=Henry|last2=Sulis|first2=William|last3=Eilam|first3=David|journal=Behavioral Neuroscience|volume=112|issue=6|pages=1475–85|pmid=9926830|hdl=11375/26795|hdl-access=free}} 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.{{Cite journal|last1=Solinas|first1=Marcello|last2=Tanda|first2=Gianluigi|last3=Wertheim|first3=Carrie E.|last4=Goldberg|first4=Steven R.|date=2016-10-08|title=Dopaminergic augmentation of delta-9-tetrahydrocannabinol (THC) discrimination: possible involvement of D2-induced formation of anandamide|pmc=2834964|journal=Psychopharmacology|volume=209|issue=2|pages=191–202|doi=10.1007/s00213-010-1789-8|issn=0033-3158|pmid=20179908}} Quinpirole may also reduce relapse in adolescent rat models of cocaine addiction.{{Cite journal|last1=Zbukvic|first1=Isabel C.|last2=Ganella|first2=Despina E.|last3=Perry|first3=Christina J.|last4=Madsen|first4=Heather B.|last5=Bye|first5=Christopher R.|last6=Lawrence|first6=Andrew J.|last7=Kim|first7=Jee Hyun|date=2016-06-01|title=Role of Dopamine 2 Receptor in Impaired Drug-Cue Extinction in Adolescent Rats|journal=Cerebral Cortex|language=en|volume=26|issue=6|pages=2895–2904|doi=10.1093/cercor/bhw051|pmid=26946126|issn=1047-3211|pmc=4869820}}

Experiments in flies found quinpirole may have neuroprotective effects against Parkinson's disease-like pathology.{{cite journal | vauthors = Wiemerslage L, Schultz BJ, Ganguly A, Lee D | title = Selective degeneration of dopaminergic neurons by MPP(+) and its rescue by D2 autoreceptors in Drosophila primary culture. | journal = J Neurochem | volume = 126 | issue = 4 | pages = 529–40 | year = 2013 | pmid = 23452092 | doi = 10.1111/jnc.12228 | pmc=3737274}} Moreover, in primary neuronal cultures it also reduces the rate of firing in dopaminergic neurons.