luzindole   Click here for help

GtoPdb Ligand ID: 1363

Synonyms: 2-benzyl-N-acetyltryptamine | N0774
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 44.89
Molecular weight 292.16
XLogP 3.45
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)NCCc1c(Cc2ccccc2)[nH]c2c1cccc2
Isomeric SMILES CC(=O)NCCc1c(Cc2ccccc2)[nH]c2c1cccc2
InChI 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)
InChI Key WVVXBPKOIZGVNS-UHFFFAOYSA-N
References
1. Audinot V, Mailliet F, Lahaye-Brasseur C, Bonnaud A, Le Gall A, Amossé C, Dromaint S, Rodriguez M, Nagel N, Galizzi JP et al.. (2003)
New selective ligands of human cloned melatonin MT1 and MT2 receptors.
Naunyn Schmiedebergs Arch Pharmacol, 367 (6): 553-61. [PMID:12764576]
2. Browning C, Beresford I, Fraser N, Giles H. (2000)
Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors.
Br J Pharmacol, 129 (5): 877-86. [PMID:10696085]
3. Dubocovich ML. (1988)
Luzindole (N-0774): a novel melatonin receptor antagonist.
J Pharmacol Exp Ther, 246 (3): 902-10. [PMID:2843633]
4. Dubocovich ML, Masana MI, Iacob S, Sauri DM. (1997)
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, 355 (3): 365-75. [PMID:9089668]
5. Dubocovich ML, Yun K, Al-Ghoul WM, Benloucif S, Masana MI. (1998)
Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms.
FASEB J, 12 (12): 1211-20. [PMID:9737724]