Luzindole (N-0774) is a selective melatonin receptor blocker (antagonist). Luzindole preferentially targets MT2 (Mel1b), with Kis of 10.2 and 158 nM for human MT2 and MT1, respectively. Luzindole inhibits experimental autoimmune encephalomyelitis and exerts antidepressant-like activity.

Physicochemical Properties

Molecular Formula	C19H20N2O
Molecular Weight	292.3749
Exact Mass	292.157
Elemental Analysis	C, 78.05; H, 6.90; N, 9.58; O, 5.47
CAS #	117946-91-5
Related CAS #	Luzindole HCl;117946-91-5;
PubChem CID	122162
Appearance	Off-white to light yellow solid powder
Density	1.2±0.1 g/cm3
Boiling Point	559.6±38.0 °C at 760 mmHg
Melting Point	44-46°C
Flash Point	292.2±26.8 °C
Vapour Pressure	0.0±1.5 mmHg at 25°C
Index of Refraction	1.632
LogP	3.04
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	5
Heavy Atom Count	22
Complexity	364
Defined Atom Stereocenter Count	0
SMILES	O=C(C([H])([H])[H])N([H])C([H])([H])C([H])([H])C1C2=C([H])C([H])=C([H])C([H])=C2N([H])C=1C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H]
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)
Chemical Name	N-[2-(2-benzyl-1H-indol-3-yl)ethyl]acetamide
Synonyms	Luzindole, N-0774, N0774, N 0774, N-acetyl-2-benzyltryptamine
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	MBP-reactive LV-4 T cell lines' antigen-specific proliferation is inhibited by luteindole (N-0774) (5–10 μg/ml) [1].
ln Vivo	Experimental autoimmune encephalomyelitis is inhibited by luzindole (N-0774) (30 mg/kg; i.p.; days 0-5) [2]. In a dose-dependent manner, luzindole (N-0774) (30 mg/kg ip) shortens immobility time; the impact is greater at midnight (60% decrease) than it is at midday (39% reduction). Luzindole's effects are time-dependent, peaking after 60 minutes. The anti-immobility effects of luzidole (10 mg/kg ip) are countered by the administration of melatonin (30 mg/kg ip). Luzindole (30 mg/kg ip) does not change albino ND/4 mice's or C57BL/6J mice's non-melatonin-producing immobility time at midday or midnight [3].
Animal Protocol	Animal/Disease Models: 23 to 12 weeks old (SJL , under minimal lighting conditions) Experimental Results: Effective prevention of experimental autoimmune encephalomyelitis.
References	[1]. 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]. 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.
Additional Infomation	Luzindole is a member of the class of indoles that is tryptamine in which one of the amino hydrogens is replaced by an acetyl group while the hydrogen at position 2 is replaced by a benzyl group. It has a role as a melatonin receptor antagonist. It is a member of acetamides and a member of indoles. It is functionally related to a tryptamine.

Solubility Data

Solubility (In Vitro)

DMSO : ~100 mg/mL (~342.03 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.4203 mL	17.1016 mL	34.2032 mL
	5 mM	0.6841 mL	3.4203 mL	6.8406 mL
	10 mM	0.3420 mL	1.7102 mL	3.4203 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.