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Luzindole

Chemical compound

Luzindole

Chemical compound

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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, with approximately 11- to 25-fold greater affinity for the MT2 over the MT1 receptor. In animal studies, it has been observed to disrupt the circadian rhythm as well as produce antidepressant effects.

Synthesis

Although the "hydrogen bomb" method was reported as 54% yield by Dubococvich, Boehringer Sohn achieved 96% for this step. The difference is that B.I. conducted their hydrogenation under normal pressure at 50°C for 5 hours, whereas Dubocovich conducted theirs at 100 lbs/in2 hydrogen heated to 35°C. This proves that the hydrogenation step proceeds favorably under milder conditions.

5283343}} (1994 to Discovery Therapeutics Inc).</ref><ref>Schroeder Dr Hans-D, et al. DE1445516 (1968 to CH Boehringer Sohn AG and Co KG).</ref>

The Pictet–Spengler reaction between tryptamine [61-54-1] (1) and benzaldehyde gives 1-Phenyl-tetrahydrocarboline [3790-45-2] (2). Catalytic hydrogenation leads to 2-Benzyltryptamine [22294-23-1] (3). Acylation with acetic anhydride only gave 21% yield of Luzindole (4).

Luzindole synthesis 2:<ref>Tsotinis, Andrew; Afroudakis, Pandelis (2008). &quot;Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis&quot;. Letters in Organic Chemistry. 5 (6): 507–509. doi:10.2174/157017808785740561. ISSN 1570-1786.</ref>

2-iodoaniline [615-43-0] (1) Propargylbenzene [10147-11-2] (2) 2-(3-phenylprop-1-ynyl)aniline, PC85868179 (3) 2-benzylindole [3377-72-8] (4) 1-Dimethylamino-2-nitroethylene [1190-92-7] (5) (6)

One pot Luzindole synthesis:

References

References

  1. Dubocovich ML. (September 1988). "Luzindole (N-0774): a novel melatonin receptor antagonist". The Journal of Pharmacology and Experimental Therapeutics.
  2. (September 1998). "Selective MT2 melatonin receptor antagonists block melatonin-mediated phase advances of circadian rhythms". The FASEB Journal.
  3. (March 2000). "Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors". [[British Journal of Pharmacology]].
  4. (July 1990). "Antidepressant-like activity of the melatonin receptor antagonist, luzindole (N-0774), in the mouse behavioral despair test". European Journal of Pharmacology.
  5. Margarita L. Dubocovich, et al. WO1989001472A1 ().
  6. Margarita L. Dubocovich, et al., {{US patent. 5283343 (1994 to Discovery Therapeutics Inc).
  7. Schroeder Dr Hans-D, et al. DE1445516 (1968 to CH Boehringer Sohn AG and Co KG).
  8. Tsotinis, Andrew; Afroudakis, Pandelis (2008). "Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis". Letters in Organic Chemistry. 5 (6): 507–509. doi:10.2174/157017808785740561. ISSN 1570-1786.
  9. Righi, Marika; Topi, Francesca; Bartolucci, Silvia; Bedini, Annalida; Piersanti, Giovanni; Spadoni, Gilberto (2012). "Synthesis of Tryptamine Derivatives via a Direct, One-Pot Reductive Alkylation of Indoles". The Journal of Organic Chemistry. 77 (14): 6351–6357. doi:10.1021/jo3010028.
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acetamides n-acyltryptamines melatonin-receptor-antagonists
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