81226-60-0

81226-60-0 structure

Name: L-741,626
Chemical Name: 4-(4-chlorophenyl)-1-(1H-indol-3-ylmethyl)piperidin-4-ol
CAS Number: 81226-60-0
Molecular Formula: C₂₀H₂₁ClN₂O
Molecular Weight: 340.84700
Catalog: Signaling Pathways GPCR/G Protein Dopamine Receptor
Create Date: 2018-12-29 08:44:53
Modify Date: 2024-01-22 18:42:18
L-741626 is a selective D2 dopamine receptor antagonist, with the Ki values of 2.4, 100 and 220 nM for human D2, D3 and D4 receptors respectively[1].

Name	4-(4-chlorophenyl)-1-(1H-indol-3-ylmethyl)piperidin-4-ol
Synonyms	4-(4-Chlorophenyl)-1-(1H-indol-3-ylmethyl)-4-piperidinol L 741,626 1-(indol-3-ylmethyl)-4-hydroxy-4-(p-chlorophenyl)piperidine 4-Piperidinol,4-(4-chlorophenyl)-1-(1H-indol-3-ylmethyl) 3-(4-(4-Chlorophenyl-4-hydroxypiperidino)methyl)indole

Description	L-741626 is a selective D2 dopamine receptor antagonist, with the Ki values of 2.4, 100 and 220 nM for human D2, D3 and D4 receptors respectively[1].
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor Research Areas >> Neurological Disease
Target	Ki: 2.4 nM (human D2 receptor), 100 nM (human D3 receptor), 220 nM (human D4 receptor)[1]
In Vitro	Intrinsic activities in a functional assay using inhibition of quinpirole stimulation of mitogenesis in human dopamine D2 or D3 receptors transfected into Chinese hamster ovary (CHO) cells, L-741626 is prepared by literature methods (Ki (D2)=11.2 nM) and displays a D3/D2 and D4/D2 selectivity ratio of 15-fold and 136-fold, respectively. In the functional assay L-741626 is a potent antagonist (EC50 (D2)=4.46 nM) with some D2 selectivity (EC50 (D3)=90.4 nM)[2].
In Vivo	L-741626 (1.0 mg/kg; i.h.) is effective at shifting to the right the pramipexole dose-response curve in pramipexole-trained male Sprague Dawley rats[3]. Coadministrating Cocaine with the D2 antagonist L-741626 (3 mg/kg; i.p.; 15 min before Cocaine) for 5 days reduces the Cocaine-induced increase in microglial TNF-α production in adult mice[4].
References	[1]. Lewitus GM, et al. Microglial TNF-α Suppresses Cocaine-Induced Plasticity and Behavioral Sensitization. Neuron. 2016 May 4;90(3):483-91. [2]. Grundt P, et al. Analogues of the dopamine D2 receptor antagonist L741,626: Binding, function, and SAR. Bioorg Med Chem Lett. 2007 Feb 1;17(3):745-9. [3]. Koffarnus MN, et al. The discriminative stimulus effects of dopamine D2- and D3-preferring agonists in rats. Psychopharmacology (Berl). 2009 Apr;203(2):317-27. [4]. Kulagowski JJ, et al. 3-((4-(4-Chlorophenyl)piperazin-1-yl)-methyl)-1H-pyrrolo-2,3-b-pyridine: an antagonist with high affinity and selectivity for the human dopamine D4 receptor. J Med Chem. 1996 May 10;39(10):1941-2.

Density	1.311g/cm3
Boiling Point	548.8ºC at 760 mmHg
Molecular Formula	C₂₀H₂₁ClN₂O
Molecular Weight	340.84700
Flash Point	285.7ºC
Exact Mass	340.13400
PSA	39.26000
LogP	4.24280
Index of Refraction	1.686

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport

120-72-9

39512-49-7

81226-60-0

Literature: John Wyeth and Brother Limited Patent: US4358456 A1, 1982 ;

87-52-5

39512-49-7

~95%

81226-60-0

Literature: Vangveravong, Suwanna; McElveen, Elizabeth; Taylor, Michelle; Xu, Jinbin; Tu, Zhude; Luedtke, Robert R.; Mach, Robert H. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 3 p. 815 - 825

Precursor 3
120-72-9 39512-49-7 87-52-5
DownStream 0

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