117946-91-5

117946-91-5 structure

Name: Luzindole
Chemical Name: N-[2-(2-benzyl-1H-indol-3-yl)ethyl]acetamide
CAS Number: 117946-91-5
Molecular Formula: C₁₉H₂₀N₂O
Molecular Weight: 292.375
Catalog: Signaling Pathways GPCR/G Protein Melatonin Receptor
Create Date: 2018-09-06 20:55:21
Modify Date: 2024-01-11 18:41:03
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. Luzindole suppresses experimental autoimmune encephalomyelitis (EAE), and exerts antidepressant-like activity[1][2][3].

Name	N-[2-(2-benzyl-1H-indol-3-yl)ethyl]acetamide
Synonyms	N-[2-(2-Benzyl-1H-indol-3-yl)ethyl]acetamide Luzindole Acetamide, N-[2-[2-(phenylmethyl)-1H-indol-3-yl]ethyl]- N-Acetyl-2-benzyltryptamine 2-Benzyl-N-acetyltryptamine N-0774 N-Acetyl-2-benzyltryptamine N-[2-[2-(Phenylmethyl)-1H-indol-3-yl]ethyl]acetamide MFCD00672498 Arachidonyl serotonin Tocris-0877

Description	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. Luzindole suppresses experimental autoimmune encephalomyelitis (EAE), and exerts antidepressant-like activity[1][2][3].
Related Catalog	Signaling Pathways >> Neuronal Signaling >> Melatonin Receptor Signaling Pathways >> GPCR/G Protein >> Melatonin Receptor Research Areas >> Neurological Disease
Target	Ki :10.2 nM (human MT2), 158 nM (human MT1)[1]
In Vitro	Luzindole (N-0774) (5-10 μg/ml) inhibits antigen-specific proliferation of the MBP-reactive LV-4 T cell line[1].
In Vivo	Luzindole (N-0774) (30 mg/kg; i.p.; days 0-5) suppresses experimental autoimmune encephalomyelitis[2]. Luzindole (N-0774) (30 mg/kg i.p.) reduces the time of immobility in a dose-dependent manner, the effect being more pronounced at midnight (60% reduction) than at noon (39% reduction). The effect of luzindole is time-dependent, showing a maximal effect at 60 min. The anti-immobility effect of luzindole (10 mg/kg i.p.) is prevented by the administration of melatonin (30 mg/kg i.p.). Luzindole (30 mg/kg i.p.) did not modify the time of immobility either at noon or midnight in the albino ND/4 mouse, or in the C57BL/6J mouse, which does not produce melatonin[3]. Animal Model: Twenty-three- to 12-week-old(SJL X PL/J ) F1 mice[2] Dosage: 30 mg/kg Administration: i.p.; days 0-5 (between 23: 00 and 1: 00 under conditions of minimal lighting) Result: Effectively prevented experimental autoimmune encephalomyelitis.
References	[1]. Dubocovich ML, et al. Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor. Naunyn Schmiedebergs Arch Pharmacol. 1997 Mar;355(3):365-75. [2]. Constantinescu CS, et al. Luzindole, a melatonin receptor antagonist, suppresses experimental autoimmune encephalomyelitis. Pathobiology. 1997;65(4):190-4. [3]. Dubocovich ML 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.

Density	1.2±0.1 g/cm3
Boiling Point	559.6±38.0 °C at 760 mmHg
Melting Point	44-46°C
Molecular Formula	C₁₉H₂₀N₂O
Molecular Weight	292.375
Flash Point	292.2±26.8 °C
Exact Mass	292.157562
PSA	44.89000
LogP	3.04
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.632
Storage condition	−20°C
Stability	Store at -20°C
Water Solubility	DMSO: 5 mg/mL

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases	S24/25
RIDADR	NONH for all modes of transport
WGK Germany	3

61-54-1

117946-91-5

Literature: US5093352 A1, ; US 5093352 A

3377-72-8

62005-48-5

~73%

117946-91-5

Literature: Journal of Organic Chemistry, , vol. 77, # 14 p. 6351 - 6357

Precursor 3
61-54-1 3377-72-8 62005-48-5
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