L 745870 Free Base | CAS# 158985-00-3 (free base) | dopamine receptor antagonist

MedKoo Cat#: 413335 | Name: L 745870 Free Base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

L 745870 Free Base is a drug which acts as a dopamine receptor antagonist selective for the D₄ subtype, and has antipsychotic effects in animal models, though it was not effective in human trials.

Chemical Structure

L 745870 Free Base

CAS#158985-00-3 (free base)

Theoretical Analysis

MedKoo Cat#: 413335

Name: L 745870 Free Base

CAS#: 158985-00-3 (free base)

Chemical Formula: C18H19ClN4

Exact Mass: 326.1298

Molecular Weight: 326.83

Elemental Analysis: C, 66.15; H, 5.86; Cl, 10.85; N, 17.14

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 320.00	2 Weeks
50mg	USD 850.00	2 Weeks

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Related CAS #

866021-03-6 (3HCl) 158985-00-3 (free base) 1173023-36-3 (HCl)

Synonym

L 745870 Free Base; L745870; L-745870

IUPAC/Chemical Name

3-((4-(4-Chlorophenyl)piperazin-1-yl)methyl)-1H-pyrrolo(2,3-b)pyridine

InChi Key

OGJGQVFWEPNYSB-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H19ClN4/c19-15-3-5-16(6-4-15)23-10-8-22(9-11-23)13-14-12-21-18-17(14)2-1-7-20-18/h1-7,12H,8-11,13H2,(H,20,21)

SMILES Code

ClC1=CC=C(N2CCN(CC3=CNC4=NC=CC=C43)CC2)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

L-745870 is a potent, selective, brain-penetrant and orally active dopamine D4 receptor antagonist with a Ki of 0.43 nM.

In vitro activity:

TBD

In vivo activity:

L-745,870 exhibited high selectivity for the dopamine D4 receptor (>2000 fold) compared to other dopamine receptor subtypes and had moderate affinity for 5HT2, sigma and alpha adrenergic receptors(IC50 < 300 nM). In vitro, L-745,870 (0.1-1 microM) exhibited D4 receptor antagonist activity, reversing dopamine (1 microM) mediated 1) inhibition of adenylate cyclase in hD4HEK and hD4CHO cells; 2) stimulation of [35S] GTPgammaS binding and 3) stimulation of extracellular acidification rate, but did not exhibit any significant intrinsic activity in these assays. Reference: J Pharmacol Exp Ther. 1997 Nov;283(2):636-47. https://pubmed.ncbi.nlm.nih.gov/9353380/

	Solvent	mg/mL	mM
Solubility
	DMSO	16.5	50.49

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 326.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Miyahara N, Ono K, Hitomi S, Hirase M, Inenaga K. Dopamine modulates neuronal excitability pre- and post-synaptically in the rat subfornical organ. Brain Res. 2012 Apr 4;1447:44-52. doi: 10.1016/j.brainres.2012.01.063. Epub 2012 Feb 2. PMID: 22356889. 2. Patel S, Freedman S, Chapman KL, Emms F, Fletcher AE, Knowles M, Marwood R, Mcallister G, Myers J, Curtis N, Kulagowski JJ, Leeson PD, Ridgill M, Graham M, Matheson S, Rathbone D, Watt AP, Bristow LJ, Rupniak NM, Baskin E, Lynch JJ, Ragan CI. Biological profile of L-745,870, a selective antagonist with high affinity for the dopamine D4 receptor. J Pharmacol Exp Ther. 1997 Nov;283(2):636-47. PMID: 9353380.

In vitro protocol:

TBD

In vivo protocol:

1: Huot P, Johnston TH, Koprich JB, Espinosa MC, Reyes MG, Fox SH, Brotchie JM. L-745,870 reduces the expression of abnormal involuntary movements in the 6-OHDA-lesioned rat. Behav Pharmacol. 2015 Feb;26(1-2):101-8. doi: 10.1097/FBP.0000000000000096. PMID: 25303957. 2: Huot P, Johnston TH, Koprich JB, Aman A, Fox SH, Brotchie JM. L-745,870 reduces L-DOPA-induced dyskinesia in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-lesioned macaque model of Parkinson's disease. J Pharmacol Exp Ther. 2012 Aug;342(2):576-85. doi: 10.1124/jpet.112.195693. Epub 2012 May 22. PMID: 22619253. 3: Baskerville TA, Allard J, Wayman C, Douglas AJ. Dopamine-oxytocin interactions in penile erection. Eur J Neurosci. 2009 Dec 3;30(11):2151-64. doi: 10.1111/j.1460-9568.2009.06999.x. Epub 2009 Nov 25. PMID: 20128851. 4: Marazziti D, Lucacchini A, Baroni S, Betti L, Catena M, Giannaccini G, Dell'Osso B, Masala I, Mungai F, Dell'Osso L. Presence of D4 dopamine receptors in human prefrontal cortex: a postmortem study. Braz J Psychiatry. 2007 Jun;29(2):148-52. doi: 10.1590/s1516-44462007000200011. PMID: 17639254. 5: Giorgioni G, Del Bello F, Pavletić P, Quaglia W, Botticelli L, Cifani C, Micioni Di Bonaventura E, Micioni Di Bonaventura MV, Piergentili A. Recent findings leading to the discovery of selective dopamine D4 receptor ligands for the treatment of widespread diseases. Eur J Med Chem. 2021 Feb 15;212:113141. doi: 10.1016/j.ejmech.2020.113141. Epub 2020 Dec 29. PMID: 33422983. 6: Gorelova N, Seamans JK, Yang CR. Mechanisms of dopamine activation of fast- spiking interneurons that exert inhibition in rat prefrontal cortex. J Neurophysiol. 2002 Dec;88(6):3150-66. doi: 10.1152/jn.00335.2002. PMID: 12466437. 7: Nakane M, Cowart MD, Hsieh GC, Miller L, Uchic ME, Chang R, Terranova MA, Donnelly-Roberts DL, Namovic MT, Miller TR, Wetter JM, Marsh K, Stewart AO, Brioni JD, Moreland RB. 2-[4-(3,4-Dimethylphenyl)piperazin-1-ylmethyl]-1H benzoimidazole (A-381393), a selective dopamine D4 receptor antagonist. Neuropharmacology. 2005 Jul;49(1):112-21. doi: 10.1016/j.neuropharm.2005.02.004. Epub 2005 Apr 1. PMID: 15992586. 8: Bristow LJ, Kramer MS, Kulagowski J, Patel S, Ragan CI, Seabrook GR. Schizophrenia and L-745,870, a novel dopamine D4 receptor antagonist. Trends Pharmacol Sci. 1997 Jun;18(6):186-8. doi: 10.1016/s0165-6147(97)01066-3. PMID: 9226994. 9: Jackson CR, Chaurasia SS, Zhou H, Haque R, Storm DR, Iuvone PM. Essential roles of dopamine D4 receptors and the type 1 adenylyl cyclase in photic control of cyclic AMP in photoreceptor cells. J Neurochem. 2009 Apr;109(1):148-57. doi: 10.1111/j.1471-4159.2009.05920.x. Epub 2009 Jan 22. PMID: 19166506; PMCID: PMC2727872. 10: Cheung TH, Bezzina G, Hampson CL, Body S, Fone KC, Bradshaw CM, Szabadi E. Effect of quinpirole on timing behaviour in the free-operant psychophysical procedure: evidence for the involvement of D2 dopamine receptors. Psychopharmacology (Berl). 2007 Aug;193(3):423-36. doi: 10.1007/s00213-007-0798-8. Epub 2007 May 6. PMID: 17484066.