A melatonin receptor antagonist
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Luzindole

Item No. 15998

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-[2-(phenylmethyl)-1H-indol-3-yl]ethyl]-acetamide
CAS Number
117946-91-5
Synonyms
  • N-0774
Molecular Formula
C19H20N2O
Formula Weight
292.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
226, 283 nm
SMILES
CC(NCCC1=C(CC2=CC=CC=C2)NC3=CC=CC=C31)=O
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)
InChi Key
WVVXBPKOIZGVNS-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $69

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    10 mg

    $120

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    25 mg

    $263

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    50 mg

    $525

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    Product Description

    In addition to intrinsic antioxidant activities, melatonin (Item No. 14427) evokes its effects through the G protein-coupled receptors MT1A (MT1) and MT1B (MT2).1 Luzindole is a melatonin receptor antagonist that preferentially targets MT1B over MT1A (Ki values are = 10-27 and 158-513 nM, respectively).2,3,4 Luzindole is used both in vitro and in vivo to evaluate the roles of melatonin receptor signaling in diverse pathways, including circadian rhythms, animal behavior, and melanophore response.2,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chan, K.H., and Wong, Y.H. A molecular and chemical perspective in defining melatonin receptor subtype selectivity. Int. J. Mol. Sci. 14(9), 18385-18406 (2013).

    2. Teh, M.T., and Sugden, D. Comparison of the structure-activity relationships of melatonin receptor agonists and antagonists: Lengthening the N-acyl side-chain has differing effects on potency on Xenopus melanophores. Naunyn Schmiedebergs Arch. Pharmacol. 358(5), 522-528 (1998).

    3. Dubocovich, M.L. Luzindole (N-0774): A novel melatonin receptor antagonist. J. Pharmacol. Exp. Ther. 246(3), 902-910 (1988).

    4. Dubocovich, M.L., Masana, M.I., Iacob, S., 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-Schmiedeberg's Arch. Pharmacol. 355(3), 365-375 (1997).

    5. Dubocovich, M.L., Yun, K., Al-Ghoul, W.M., et al. Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms. The FASEB Journal 12(12), 1211-1220 (1998).

    6. Laredo, S.A., Orr, V.N., McMackin, M.Z., et al. The effects of exogenous melatonin and melatonin receptor blockade on aggression and estrogen-dependent gene expression in male California mice (Peromyscus californicus). Physiol. Behav. 128, 86-91 (2014).