QUINELORANE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H22N4
Molecular Weight	246.3513
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CCCN(CCC)[C@]1([H])CC3=C(C2)N=C(N)N=C3

InChI

InChIKey=TUFADSGTJUOBEH-ZWNOBZJWSA-N

InChI=1S/C14H22N4/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)/t10-,13-/m1/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1673422 | https://www.ncbi.nlm.nih.gov/pubmed/1833778 | https://www.ncbi.nlm.nih.gov/pubmed/18579193

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17976986	Agonist 2678		2.0 nM [EC50]
Dopamine D3 receptor 91 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17976986	Agonist 2678		1.0 nM [EC50]

PubMed

Title	Date	PubMed
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	7473180
Evidence to suggest that agonist modulation of hyperlocomotion is via post-synaptic dopamine D2 or D3 receptors.	1997 Jun	9225306
Effects of dopamine D(1-like) and D(2-like) agonists in rats that self-administer cocaine.	1999 Oct	10490924
Previous exposure to amphetamine enhances the subsequent locomotor response to a D1 dopamine receptor agonist when glutamate reuptake is inhibited.	2001 Mar 1	11222671
Dopaminergic inhibition of secretin-stimulated choleresis by increased PKC-gamma expression and decrease of PKA activity.	2003 Apr	12505882
Respective roles of dopamine D2 and D3 receptors in food-seeking behaviour in rats.	2003 Feb	12525958
Facilitatory effect of the dopamine D4 receptor agonist PD168,077 on memory consolidation of an inhibitory avoidance learned response in C57BL/6J mice.	2003 Jun 16	12798264
The modulatory actions of dopamine D2/3 agonists and antagonists on the locomotor-activating effects of morphine and caffeine in mice.	2003 May	12873628
Gradient of dopamine responsiveness to dopamine receptor agonists in subregions of the rat nucleus accumbens.	2003 Sep 12	14519414
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	15464142
Modulation of the discriminative stimulus effects of mu opioid agonists in rats: II. Effects of dopamine D2/3 agonists.	2004 Feb	15075629
Protection against cocaine toxicity in mice by the dopamine D3/D2 agonist R-(+)-trans-3,4a,10b-tetrahydro-4-propyl-2H,5H-[1]benzopyrano[4,3-b]-1,4-oxazin-9-ol [(+)-PD 128,907].	2004 Mar	14711932
Differential effects of dopaminergic agents on locomotor sensitisation and on the reinstatement of cocaine-seeking and food-seeking behaviour.	2004 Oct	15064914
Physicochemical modulation of agonist-induced [35s]GTPgammaS binding: implications for coexistence of multiple functional conformations of dopamine D1-like receptors.	2005	16149770
Mapping the effects of the selective dopamine D2/D3 receptor agonist quinelorane using pharmacological magnetic resonance imaging.	2005	15893653
A reconfiguration of CaV2 Ca2+ channel current and its dopaminergic D2 modulation in developing neostriatal neurons.	2005 Dec	16120665
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	15494551
Perinatal exposure to low levels of the environmental antiandrogen vinclozolin alters sex-differentiated social play and sexual behaviors in the rat.	2005 Jun	15929892
D2-like receptors mediate the expulsion phase of ejaculation elicited by 8-hydroxy-2-(di-N-propylamino)tetralin in rats.	2006 Feb	16221741
Dopamine transporter (DAT) inhibitors alleviate specific parkinsonian deficits in monkeys: association with DAT occupancy in vivo.	2006 Nov	16885433
Action of novel antipsychotics at human dopamine D3 receptors coupled to G protein and ERK1/2 activation.	2007 Aug	17588617
Lack of self-administration of cocaine in dopamine D1 receptor knock-out mice.	2007 Nov 28	18045908
Decrease of D2 receptor binding but increase in D2-stimulated G-protein activation, dopamine transporter binding and behavioural sensitization in brains of mice treated with a chronic escalating dose 'binge' cocaine administration paradigm.	2008 Aug	18671743
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	19756524
Penile erection and yawning induced by dopamine D2-like receptor agonists in rats: influence of strain and contribution of dopamine D2, but not D3 and D4 receptors.	2009 Jul	19584712

Patents

Sample Use Guides

In Vivo Use Guide

2.5 or 5 micrograms/kg

Route of Administration: Oral

Name

Type

Language

QUINELORANE

Official Name

English

quinelorane [INN]

Common Name

English

(-)-(5AR,9AR)-2-AMINO-5,5A,6,7,8,9,9A,10-OCTAHYDRO-6-PROPYLPYRIDO(2,3-G)QUINAZOLINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884