Luzindole | CAS#117946-91-5 | melatonin receptor antagonist

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

MedKoo CAT#: 329876

CAS#: 117946-91-5 (free base)

Description: Luzindole, also known as N-0774, and N-acetyl-2-benzyltryptamine, is a melatonin receptor antagonist that preferentially targets MT1B over MT1A (Ki values are = 10-27 and 158-513 nM, respectively). Luzindole induces the activation of cellular stress responses and decreases viability of rat pancreatic stellate cells. Luzindole inhibits the transient outward K+ current in rat cerebellar granule cells. Luzindole suppresses experimental autoimmune encephalomyelitis.

Chemical Structure

Luzindole

CAS# 117946-91-5 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329876
Name: Luzindole
CAS#: 117946-91-5 (free base)
Chemical Formula: C19H20N2O
Exact Mass: 292.16
Molecular Weight: 292.382
Elemental Analysis: C, 78.05; H, 6.90; N, 9.58; O, 5.47

Price and Availability

Size	Price	Availability
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1250	2 Weeks
500mg	USD 1950	2 Weeks
1g	USD 2950	2 Weeks
2g	USD 5150	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: Luzindole HCl 117946-91-5 (free base)

Synonym: Luzindole, N-0774, N0774, N 0774, N-acetyl-2-benzyltryptamine

IUPAC/Chemical Name: N-Acetyl-2-benzyltryptamine

InChi Key: WVVXBPKOIZGVNS-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H20N2O/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)

SMILES Code: O=C(NCCC1=C(CC2=CC=CC=C2)NC3=CC=CC=C13)C

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

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Product Data:

Product Data

Instruction:

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Biological target:	Luzindole (N-0774) is a selective melatonin receptor antagonist. Luzindole preferentially targets MT2 (Mel1b) over MT1 (Mel1a) with Ki values of 10.2 and 158 nM for human MT2 and MT1, respectively.
In vitro activity:	This study examined the effects of luzindole, a melatonin receptor-antagonist, on cultured pancreatic stellate cells. Luzindole induced a concentration-dependent increase in ROS generation, both in the cytosol and in the mitochondria. In the presence of luzindole the phosphorylation of p44/42 and p38 MAPKs was increased, whereas no changes in the phosphorylation of JNK could be noted. Moreover, the detection of the endoplasmic reticulum stress-sensor BiP was increased in the presence of luzindole. Finally, viability was decreased in cells treated with luzindole. Reference: J Appl Toxicol. 2020 Nov;40(11):1554-1565. https://pubmed.ncbi.nlm.nih.gov/32567733/
In vivo activity:	Mice treated with Luzindole, LPS, and Luzindole+LPS showed villus height shortening. The Luzindole group showed an increase in NP-SHs, an effect related to compensatory GSH activity. The acute blockade of endogenous MLT with Luzindole induced early changes in inflammatory markers with altered intestinal morphology. Reference: Braz J Med Biol Res. 2021 Aug 20;54(11):e11215. https://pubmed.ncbi.nlm.nih.gov/34431873/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	25.0	85.50
	DMF	30.0	102.61
	Ethanol	39.1	133.66
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.71

Preparing Stock Solutions

The following data is based on the product molecular weight 292.38 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. Estaras M, Marchena AM, Fernandez-Bermejo M, Mateos JM, Vara D, Roncero V, Salido GM, Gonzalez A. The melatonin receptor antagonist luzindole induces the activation of cellular stress responses and decreases viability of rat pancreatic stellate cells. J Appl Toxicol. 2020 Nov;40(11):1554-1565. doi: 10.1002/jat.4018. Epub 2020 Jun 22. PMID: 32567733. 2. 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. 3. Matos RS, Oriá RB, Bruin PFC, Pinto DV, Viana AFSC, Santos FA, Duarte ASG, Bruin VMS. Acute blockade of endogenous melatonin by Luzindole, with or without peripheral LPS injection, induces jejunal inflammation and morphological alterations in Swiss mice. Braz J Med Biol Res. 2021 Aug 20;54(11):e11215. doi: 10.1590/1414-431X2021e11215. PMID: 34431873; PMCID: PMC8389610. 4. 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.
In vitro protocol:	1. Estaras M, Marchena AM, Fernandez-Bermejo M, Mateos JM, Vara D, Roncero V, Salido GM, Gonzalez A. The melatonin receptor antagonist luzindole induces the activation of cellular stress responses and decreases viability of rat pancreatic stellate cells. J Appl Toxicol. 2020 Nov;40(11):1554-1565. doi: 10.1002/jat.4018. Epub 2020 Jun 22. PMID: 32567733. 2. 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.
In vivo protocol:	1. Matos RS, Oriá RB, Bruin PFC, Pinto DV, Viana AFSC, Santos FA, Duarte ASG, Bruin VMS. Acute blockade of endogenous melatonin by Luzindole, with or without peripheral LPS injection, induces jejunal inflammation and morphological alterations in Swiss mice. Braz J Med Biol Res. 2021 Aug 20;54(11):e11215. doi: 10.1590/1414-431X2021e11215. PMID: 34431873; PMCID: PMC8389610. 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.

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1: 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. PubMed PMID: 25554981.

2: Drobnik J, Owczarek K, Piera L, Tosik D, Olczak S, Ciosek J, Hrabec E. Melatonin-induced augmentation of collagen deposition in cultures of fibroblasts and myofibroblasts is blocked by luzindole--a melatonin membrane receptors inhibitor. Pharmacol Rep. 2013;65(3):642-9. PubMed PMID: 23950586.

3: 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. PubMed PMID: 27025603; PubMed Central PMCID: PMC4888357.

4: 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. PubMed PMID: 26686389.

5: 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. PubMed PMID: 23215791.

6: 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. PubMed PMID: 20035258.

7: Dubocovich ML. Luzindole (N-0774): a novel melatonin receptor antagonist. J Pharmacol Exp Ther. 1988 Sep;246(3):902-10. PubMed PMID: 2843633.

8: 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. PubMed PMID: 12706258.

9: 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. PubMed PMID: 16098095.

10: 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. PubMed PMID: 18077581.

11: Drazen DL, Bilu D, Bilbo SD, Nelson RJ. Melatonin enhancement of splenocyte proliferation is attenuated by luzindole, a melatonin receptor antagonist. Am J Physiol Regul Integr Comp Physiol. 2001 May;280(5):R1476-82. PubMed PMID: 11294771.

12: 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. PubMed PMID: 9804154.

13: 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. PubMed PMID: 2168835.

14: Constantinescu CS, Hilliard B, Ventura E, Rostami A. Luzindole, a melatonin receptor antagonist, suppresses experimental autoimmune encephalomyelitis. Pathobiology. 1997;65(4):190-4. PubMed PMID: 9396042.

15: Schwartz C, Ballinger MA, Andrews MT. Melatonin receptor signaling contributes to neuroprotection upon arousal from torpor in thirteen-lined ground squirrels. Am J Physiol Regul Integr Comp Physiol. 2015 Nov 15;309(10):R1292-300. doi: 10.1152/ajpregu.00292.2015. Epub 2015 Sep 9. PubMed PMID: 26354846; PubMed Central PMCID: PMC4666939.

16: Mathes AM, Wolf B, Rensing H. Melatonin receptor antagonist luzindole is a powerful radical scavenger in vitro. J Pineal Res. 2008 Oct;45(3):337-8. doi: 10.1111/j.1600-079X.2008.00583.x. Epub 2008 Mar 3. PubMed PMID: 18318703.

17: Ogiwara K, Takahashi T. A Dual Role for Melatonin in Medaka Ovulation: Ensuring Prostaglandin Synthesis and Actin Cytoskeleton Rearrangement in Follicular Cells. Biol Reprod. 2016 Mar;94(3):64. doi: 10.1095/biolreprod.115.133827. Epub 2016 Feb 10. PubMed PMID: 26864196.

18: Fink T, Glas M, Wolf A, Kleber A, Reus E, Wolff M, Kiefer D, Wolf B, Rensing H, Volk T, Mathes AM. Melatonin receptors mediate improvements of survival in a model of polymicrobial sepsis. Crit Care Med. 2014 Jan;42(1):e22-31. doi: 10.1097/CCM.0b013e3182a63e2b. PubMed PMID: 24145838.

19: 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. PubMed PMID: 18594966.

20: Wu JZ, Wu WH, He LJ, Ke QF, Huang L, Dai ZS, Chen Y. Effect of Melatonin and Calmodulin in an Idiopathic Scoliosis Model. Biomed Res Int. 2016;2016:8460291. doi: 10.1155/2016/8460291. Epub 2016 Nov 30. PubMed PMID: 28042574; PubMed Central PMCID: PMC5155075.

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