Luzindole HCl | CAS#117946-91-5 | Melatonin receptor antagonist

MedKoo Cat#: 534878 | Name: Luzindole HCl

Description:

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

Luzindole, also known as N-0774, and N-acetyl-2-benzyltryptamine, is a drug used in scientific research to study the role of melatonin in the body. Luzindole acts as a selective melatonin receptor antagonist, with approximately 11- to 25-fold greater affinity for the MT2 over the MT1 receptor. In animal studies, it has been observed to disrupt the circadian rhythm as well as produce antidepressant effects.

Chemical Structure

Luzindole HCl

CAS#Luzindole HCl

Theoretical Analysis

MedKoo Cat#: 534878

Name: Luzindole HCl

CAS#: Luzindole HCl

Chemical Formula: C19H21ClN2O

Exact Mass: 0.0000

Molecular Weight: 328.84

Elemental Analysis: C, 69.40; H, 6.44; Cl, 10.78; N, 8.52; O, 4.87

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

Luzindole HCl 117946-91-5 (free base)

Synonym

Luzindole; N-0774; N0774; N 0774; N-acetyl-2-benzyltryptamine; Luzindole HCl; Luzindole hydrochloride;

IUPAC/Chemical Name

Acetamide, N-(2-(2-(phenylmethyl)-1H-indol-3-yl)ethyl)- hydrochloride

InChi Key

MYOZBJOKALEGEM-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H20N2O.ClH/c1-14(22)20-12-11-17-16-9-5-6-10-18(16)21-19(17)13-15-7-3-2-4-8-15;/h2-10,21H,11-13H2,1H3,(H,20,22);1H

SMILES Code

CC(NCCC1=C(CC2=CC=CC=C2)NC3=C1C=CC=C3)=O.[H]Cl

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

>3 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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 328.84 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

1: Estaras M, Ameur FZ, Roncero V, Fernandez-Bermejo M, Blanco G, Lopez D, Mateos JM, Salido GM, Gonzalez A. The melatonin receptor antagonist luzindole induces Ca2+ mobilization, reactive oxygen species generation and impairs trypsin secretion in mouse pancreatic acinar cells. Biochim Biophys Acta Gen Subj. 2019 Nov;1863(11):129407. doi: 10.1016/j.bbagen.2019.07.016. Epub 2019 Aug 2. PMID: 31381958. 2: Luo Y, Yang Y, Shen Y, Li L, Huang J, Tang L, Zhang L. Luzindole attenuates LPS/d-galactosamine-induced acute hepatitis in mice. Innate Immun. 2020 May;26(4):319-327. doi: 10.1177/1753425919890912. Epub 2019 Nov 28. PMID: 31779498; PMCID: PMC7251793. 3: Yang S, Zheng C, Jiang J, Lu F, Xia X, Zhu W, Jin X, Ma X. The value of applying a melatonin antagonist (Luzindole) in improving the success rate of the bipedal rat scoliosis model. BMC Musculoskelet Disord. 2017 Apr 4;18(1):137. doi: 10.1186/s12891-017-1500-x. PMID: 28376758; PMCID: PMC5379722. 4: Zhou MO, Jiao S, Liu Z, Zhang ZH, Mei YA. Luzindole, a melatonin receptor antagonist, inhibits the transient outward K+ current in rat cerebellar granule cells. Brain Res. 2003 Apr 25;970(1-2):169-77. doi: 10.1016/s0006-8993(03)02332-1. PMID: 12706258. 5: Li X, Cai S, Yin W, Hu X, Zhang S, Li Z, Li X, Laudon M. Role of Neu-p11/luzindole in the regulation of insulin signaling pathways and insulin resistance. Acta Biochim Biophys Sin (Shanghai). 2016 May;48(5):485-6. doi: 10.1093/abbs/gmw015. Epub 2016 Mar 29. PMID: 27025603; PMCID: PMC4888357. 6: Dubocovich ML. Luzindole (N-0774): a novel melatonin receptor antagonist. J Pharmacol Exp Ther. 1988 Sep;246(3):902-10. PMID: 2843633. 7: Juszczak M, Roszczyk M, Kowalczyk E, Stempniak B. The influence od melatonin receptors antagonists, luzindole and 4-phenyl-2-propionamidotetralin (4-P-PDOT), on melatonin-dependent vasopressin and adrenocorticotropic hormone (ACTH) release from the rat hypothalamo-hypophysial system. In vitro and in vivo studies. J Physiol Pharmacol. 2014 Dec;65(6):777-84. PMID: 25554981. 8: Winczyk K, Fuss-Chmielewska J, Lawnicka H, Pawlikowski M, Karasek M. Luzindole but not 4-phenyl-2- propionamidotetralin (4P-PDOT) diminishes the inhibitory effect of melatonin on murine Colon 38 cancer growth in vitro. Neuro Endocrinol Lett. 2009;30(5):657-62. PMID: 20035258. 9: Requintina PJ, Oxenkrug GF. Effect of luzindole and other melatonin receptor antagonists on iron- and lipopolysaccharide-induced lipid peroxidation in vitro. Ann N Y Acad Sci. 2007 Dec;1122:289-94. doi: 10.1196/annals.1403.021. PMID: 18077581. 10: Umit UM, Berna T, Handan K, Ipek E, Berrak Y, Can E, Bahadir GM. Role of melatonin and luzindole in rat mammary cancer. J Invest Surg. 2012 Dec;25(6):345-53. doi: 10.3109/08941939.2012.665570. PMID: 23215791. 11: Ortiz-López L, Pérez-Beltran C, Ramírez-Rodríguez G. Chronic administration of a melatonin membrane receptor antagonist, luzindole, affects hippocampal neurogenesis without changes in hopelessness-like behavior in adult mice. Neuropharmacology. 2016 Apr;103:211-21. doi: 10.1016/j.neuropharm.2015.11.030. Epub 2015 Dec 12. PMID: 26686389. 12: Dubocovich ML, Mogilnicka E, Areso PM. Antidepressant-like activity of the melatonin receptor antagonist, luzindole (N-0774), in the mouse behavioral despair test. Eur J Pharmacol. 1990 Jul 3;182(2):313-25. doi: 10.1016/0014-2999(90)90290-m. PMID: 2168835. 13: Sugawara T, Sieving PA, Iuvone PM, Bush RA. The melatonin antagonist luzindole protects retinal photoreceptors from light damage in the rat. Invest Ophthalmol Vis Sci. 1998 Nov;39(12):2458-65. PMID: 9804154. 14: Azim MS, Agarwal NB, Vohora D. Effects of agomelatine on pentylenetetrazole- induced kindling, kindling-associated oxidative stress, and behavioral despair in mice and modulation of its actions by luzindole and 1-(m-chlorophenyl) piperazine. Epilepsy Behav. 2017 Jul;72:140-144. doi: 10.1016/j.yebeh.2017.03.019. Epub 2017 Jun 7. PMID: 28578215. 15: Constantinescu CS, Hilliard B, Ventura E, Rostami A. Luzindole, a melatonin receptor antagonist, suppresses experimental autoimmune encephalomyelitis. Pathobiology. 1997;65(4):190-4. doi: 10.1159/000164122. PMID: 9396042. 16: Sumaya IC, Masana MI, Dubocovich ML. The antidepressant-like effect of the melatonin receptor ligand luzindole in mice during forced swimming requires expression of MT2 but not MT1 melatonin receptors. J Pineal Res. 2005 Sep;39(2):170-7. doi: 10.1111/j.1600-079X.2005.00233.x. PMID: 16098095. 17: Valero N, Nery A, Bonilla E, Espina LM, Chacin-Bonilla L, Añez F, Maldonado M, Meleán E. Antagonistic effect of luzindole in mice treated with melatonin during the infection with the venezuelan equine encephalomyelitis virus. Neurochem Res. 2009 Feb;34(2):268-73. doi: 10.1007/s11064-008-9766-x. Epub 2008 Jul 2. PMID: 18594966. 18: Fang J, Yan Y, Teng X, Wen X, Li N, Peng S, Liu W, Donadeu FX, Zhao S, Hua J. Melatonin prevents senescence of canine adipose-derived mesenchymal stem cells through activating NRF2 and inhibiting ER stress. Aging (Albany NY). 2018 Oct 25;10(10):2954-2972. doi: 10.18632/aging.101602. PMID: 30362962; PMCID: PMC6224246. 19: Mannino G, Caradonna F, Cruciata I, Lauria A, Perrone A, Gentile C. Melatonin reduces inflammatory response in human intestinal epithelial cells stimulated by interleukin-1β. J Pineal Res. 2019 Oct;67(3):e12598. doi: 10.1111/jpi.12598. Epub 2019 Aug 19. PMID: 31349378. 20: Butterweck V, Brattstroem A, Grundmann O, Koetter U. Hypothermic effects of hops are antagonized with the competitive melatonin receptor antagonist luzindole in mice. J Pharm Pharmacol. 2007 Apr;59(4):549-52. doi: 10.1211/jpp.59.4.0009. PMID: 17430638.