CAS Registry Number: 73-31-4
CAS Name: N-[2-(5-Methoxy-1H-indol-3-yl)ethyl]acetamide
Additional Names: N-acetyl-5-methoxytryptamine
Trademarks: Regulin (Young)
Molecular Formula: C13H16N2O2
Molecular Weight: 232.28
Percent Composition: C 67.22%, H 6.94%, N 12.06%, O 13.78%
Literature References: A hormone of the pineal gland, also produced by extra-pineal tissues, that lightens skin color in amphibians by reversing the darkening effect of MSH, q.v. Melatonin has been postulated as the mediator of photic-induced antigonadotrophic activity in photoperiodic mammals and has also been shown to be involved in thermoregulation in some ectotherms and in affecting locomotor activity rhythms in sparrows. Isoln from the pineal glands of beef cattle: Lerner et al., J. Am. Chem. Soc. 80, 2587 (1958); Wurtman et al., Science 141, 277 (1963). Structure: Lerner et al., J. Am. Chem. Soc. 81, 6084 (1959). Crystal and molecular structure: A. Wakahara, Chem. Lett. 1972, 1139. Synthesis from 5-methoxyindole as starting material by two different routes: Szmuszkovicz et al., J. Org. Chem. 25, 857 (1960). Biochemical role of melatonin: Chem. Eng. News 45, 40 (May 1, 1967). Pharmacological studies: Barchas et al., Nature 214, 919 (1967). Identification of antigonadal action sites in mouse brain: J. D. Glass, G. R. Lynch, Science 214, 821 (1981). Binding studies in human hypothalamus: S. M. Reppert et al., Science 242, 78 (1988). Efficacy in control of estrus in red deer: G. W. Asher, Anim. Reprod. Sci. 22, 145 (1990). Reviews: M. K. Vaughn, Int. J. Rev. Physiol. 24, 41-95 (1981); D. C.Klein et al., Life Sci. 28, 1975-1986 (1981). Book: Advan. Biosci. vol. 29, N. Birau, W. Schlott, Eds. (Pergamon Press, New York, 1981) 420 pp. Review of etiological role in clinical disease: A. Miles, D. Philbrick, Crit. Rev. Clin. Lab. Sci. 25, 231-253 (1987); in psychiatric disorders: eidem, Biol. Psychiatry 23, 405-425 (1988).
Properties: Pale yellow leaflets from benzene, mp 116-118°. uv max: 223, 278 nm (e 27550, 6300).
Melting point: mp 116-118°
Absorption maximum: uv max: 223, 278 nm (e 27550, 6300)
Therap-Cat-Vet: Control of estrus.