Luzindole

Luzindole (N-0774), (N-acetyl-2-benzyltryptamine), is a drug used in scientific research to study the role of melatonin in the body. Luzindole acts as a selective melatonin receptor antagonist,[1] with approximately 11- to 25-fold greater affinity for the MT₂ over the MT₁ receptor.[2][3] In animal studies, it has been observed to disrupt the circadian rhythm as well as produce antidepressant effects.[2][4]

Luzindole

Clinical data
ATC code	None
Legal status
Legal status	In general: non-regulated
Identifiers
IUPAC name N-[2-(2-benzyl-1H-indol-3-yl)ethyl]acetamide
CAS Number	117946-91-5
PubChem CID	122162
ChemSpider	108959
ChEBI	CHEBI:131788^Y
CompTox Dashboard (EPA)	DTXSID40151969
Chemical and physical data
Formula	C19H20N2O
Molar mass	292.382 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(NCCc2c1ccccc1[nH]c2Cc3ccccc3)C
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) Key:WVVXBPKOIZGVNS-UHFFFAOYSA-N

References

1. Dubocovich ML (September 1988). "Luzindole (N-0774): a novel melatonin receptor antagonist". The Journal of Pharmacology and Experimental Therapeutics. 246 (3): 902–10. PMID 2843633.
2. Dubocovich ML, Yun K, Al-Ghoul WM, Benloucif S, Masana MI (September 1998). "Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms". The FASEB Journal. 12 (12): 1211–20. doi:10.1096/fasebj.12.12.1211. PMID 9737724.
3. Browning C, Beresford I, Fraser N, Giles H (March 2000). "Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors". British Journal of Pharmacology. 129 (5): 877–86. doi:10.1038/sj.bjp.0703130. PMC 1571913. PMID 10696085.
4. Dubocovich ML, Mogilnicka E, Areso PM (July 1990). "Antidepressant-like activity of the melatonin receptor antagonist, luzindole (N-0774), in the mouse behavioral despair test". European Journal of Pharmacology. 182 (2): 313–25. doi:10.1016/0014-2999(90)90290-M. PMID 2168835.