Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H22N4.2ClH |
| Molecular Weight | 319.273 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.[H][C@]12CCCN(CCC)[C@]1([H])CC3=C(C2)N=C(N)N=C3
InChI
InChIKey=WDEMLQIGYYLRRX-OWVUFADGSA-N
InChI=1S/C14H22N4.2ClH/c1-2-5-18-6-3-4-10-7-12-11(8-13(10)18)9-16-14(15)17-12;;/h9-10,13H,2-8H2,1H3,(H2,15,16,17);2*1H/t10-,13-;;/m1../s1
| Molecular Formula | C14H22N4 |
| Molecular Weight | 246.3513 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Quinelorane is an octahydropyrimido[4,5-g]quinolone derivative patented by American pharmaceutical company Eli Lilly and Co. as for the treatment anxiety, Parkinson's syndrome, depression, and hypertension. Quinelorane acts as an agonist of dopamine agonist for the D2 and D3 receptors. In preclinical studies Quinelorane (IM) treatment produced dose-dependent effects on male sexual responding. Penile erections and masturbation were markedly facilitated following treatment with either 2.5 or 5 micrograms/kg quinelorane. Higher doses of quinelorane (10 and 25 micrograms/kg) generally did not further augment sexual responding but rather resulted in a return in sexual responding to control vehicle levels. Quinelorane had a biphasic effect on yawning behavior of the monkeys with low doses (2.5 and 5 micrograms/kg) facilitating yawning and high doses (25 micrograms/kg) inhibiting yawning.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Observations on the absorption, distribution, metabolism, and excretion of the dopamine (D2) agonist, quinelorane, in rats, mice, dogs, and monkeys. | 1991 Jan-Feb |
|
| Pharmacology of human dopamine D3 receptor expressed in a mammalian cell line: comparison with D2 receptor. | 1992 Apr 10 |
|
| Functional correlates of dopamine D3 receptor activation in the rat in vivo and their modulation by the selective antagonist, (+)-S 14297: 1. Activation of postsynaptic D3 receptors mediates hypothermia, whereas blockade of D2 receptors elicits prolactin secretion and catalepsy. | 1995 Nov |
|
| Effects of dopamine D(1-like) and D(2-like) agonists in rats that self-administer cocaine. | 1999 Oct |
|
| Discriminative stimulus properties of the dopamine D3 receptor agonists, PD128,907 and 7-OH-DPAT: a comparative characterization with novel ligands at D3 versus D2 receptors. | 2000 Feb 14 |
|
| Role of dopamine D3 receptors in thermoregulation: a reappraisal. | 2000 Jan 17 |
|
| Nonlinear analysis of partial dopamine agonist effects on cAMP in C6 glioma cells. | 2001 Jan-Feb |
|
| An investigation of the mechanisms responsible for acute fluoxetine-induced anxiogenic-like effects in mice. | 2001 Jun |
|
| Signal transduction interactions between CB1 cannabinoid and dopamine receptors in the rat and monkey striatum. | 2001 Jun |
|
| Previous exposure to amphetamine enhances the subsequent locomotor response to a D1 dopamine receptor agonist when glutamate reuptake is inhibited. | 2001 Mar 1 |
|
| Influence of social isolation and 6-OHDA lesion on the effects of quinelorane. | 2001 May-Jun |
|
| Dopamine D2 receptor-mediated G-protein activation in rat striatum: functional autoradiography and influence of unilateral 6-hydroxydopamine lesions of the substantia nigra. | 2001 Nov 30 |
|
| In vivo characterization of basal amino acid levels in subregions of the rat nucleus accumbens: effect of a dopamine D(3)/D(2) agonist. | 2001 Sep |
|
| Role of dopamine D2-like receptors in cocaine self-administration: studies with D2 receptor mutant mice and novel D2 receptor antagonists. | 2002 Apr 1 |
|
| Dopamine D1/5 receptor stimulation induces c-fos expression in the subthalamic nucleus: possible involvement of local D5 receptors. | 2002 Jan |
|
| D2-like receptor-mediated inhibition of Na+-K+-ATPase activity is dependent on the opening of K+ channels. | 2002 Jul |
|
| Piribedil enhances frontocortical and hippocampal release of acetylcholine in freely moving rats by blockade of alpha 2A-adrenoceptors: a dialysis comparison to talipexole and quinelorane in the absence of acetylcholinesterase inhibitors. | 2003 Apr |
|
| Respective roles of dopamine D2 and D3 receptors in food-seeking behaviour in rats. | 2003 Feb |
|
| Effects of dopamine indirect agonists and selective D1-like and D2-like agonists and antagonists on cocaine self-administration and food maintained responding in rats. | 2004 |
|
| Quantification and pharmacological characterization of dialysate levels of noradrenaline in the striatum of freely-moving rats: release from adrenergic terminals and modulation by alpha2-autoreceptors. | 2004 Dec 30 |
|
| Modulation of the discriminative stimulus effects of mu opioid agonists in rats: II. Effects of dopamine D2/3 agonists. | 2004 Feb |
|
| Blockade by the cannabinoid CB1 receptor antagonist, rimonabant (SR141716), of the potentiation by quinelorane of food-primed reinstatement of food-seeking behavior. | 2004 May |
|
| Physicochemical modulation of agonist-induced [35s]GTPgammaS binding: implications for coexistence of multiple functional conformations of dopamine D1-like receptors. | 2005 |
|
| Mapping the effects of the selective dopamine D2/D3 receptor agonist quinelorane using pharmacological magnetic resonance imaging. | 2005 |
|
| A reconfiguration of CaV2 Ca2+ channel current and its dopaminergic D2 modulation in developing neostriatal neurons. | 2005 Dec |
|
| Dopamine D1 and D2 agonist effects on prepulse inhibition and locomotion: comparison of Sprague-Dawley rats to Swiss-Webster, 129X1/SvJ, C57BL/6J, and DBA/2J mice. | 2005 Feb |
|
| Delta-9-tetrahydrocannabinol differentially suppresses emesis versus enhanced locomotor activity produced by chemically diverse dopamine D2/D3 receptor agonists in the least shrew (Cryptotis parva). | 2005 Jan |
|
| Distinct temporal phases in the behavioral pharmacology of LSD: dopamine D2 receptor-mediated effects in the rat and implications for psychosis. | 2005 Jul |
|
| Perinatal exposure to low levels of the environmental antiandrogen vinclozolin alters sex-differentiated social play and sexual behaviors in the rat. | 2005 Jun |
|
| Dopamine D3 modulation of locomotor activity and sleep in the nucleus accumbens and in lobules 9 and 10 of the cerebellum in the rat. | 2005 Jun |
|
| D2-like receptors mediate the expulsion phase of ejaculation elicited by 8-hydroxy-2-(di-N-propylamino)tetralin in rats. | 2006 Feb |
|
| Dopamine transporter (DAT) inhibitors alleviate specific parkinsonian deficits in monkeys: association with DAT occupancy in vivo. | 2006 Nov |
|
| Effects of selective dopamine D1-like and D2-like agonists on prepulse inhibition of startle in inbred C3H/HeJ, SPRET/EiJ, and CAST/EiJ mice. | 2007 Apr |
|
| Action of novel antipsychotics at human dopamine D3 receptors coupled to G protein and ERK1/2 activation. | 2007 Aug |
|
| Yawning and hypothermia in rats: effects of dopamine D3 and D2 agonists and antagonists. | 2007 Aug |
|
| Insulin replacement restores the behavioral effects of quinpirole and raclopride in streptozotocin-treated rats. | 2007 Mar |
|
| Lack of self-administration of cocaine in dopamine D1 receptor knock-out mice. | 2007 Nov 28 |
|
| Lack of D2 receptor mediated regulation of dopamine synthesis in A11 diencephalospinal neurons in male and female mice. | 2008 Jun 12 |
|
| Neural basis for a heritable phenotype: differences in the effects of apomorphine on startle gating and ventral pallidal GABA efflux in male Sprague-Dawley and Long-Evans rats. | 2009 Dec |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:00:41 UTC 2023
by
admin
on
Fri Dec 15 18:00:41 UTC 2023
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| Record UNII |
JT5527J55O
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C66884
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C152122
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68728
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DTXSID60913869
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CHEMBL155731
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97548-97-5
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X-99
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JT5527J55O
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