MYOSMINE

Description

The alkaloids found in tobacco smoke may be separated into those which are volatile in steam and those which are non-volatile. Myosmine occurs in the former group and, although only present in small quantities, is the most fully investigated of these bases. The alkaloid is normally obtained as an oily liquid which may be crystallized. It is optically inactive and readily soluble in light petroleum or Et20. It forms a hydrochloride as a microcrystalline powder which, on sublimation yields colourless rods, m.p. ISS-8°C. The dihydrochloride, also a microcrystalline powder, yields colourless needles on sublimation, m.p. 1S0- 17 Soc. The base also furnishes a dipicrate, m.p. 182-3°C (dec.) and a dipi_x0002_crolonate, m.p. 204°C (dec.). On dehydrogenation it gives 2-(3'-pyridyl)-pyrrole (picrate, m.p. 200°C) identical with that obtained in a similar manner from nornicotine. According to Woodward and his colleagues, the alkaloid is one of several products formed when nicotine is dehydrogenated over prepared quartz at S70°C. It is readily hydrolyzed in H20 to yield 3-pyridyl-r-aminopropyl ketone, forming a crystalline phenylhydrazone, m.p. 20l-2°C.

Chemical properties

Light Yellow Powder

The Uses of MYOSMINE

Myosmine is an alkaloid found in tobacco. Myosmine has been suspected to be a tobacco-independent carcinogenic source.

The Uses of MYOSMINE

mitogen

The Uses of MYOSMINE

Tobacco alkaloid

Reactant for:
Nitrosation reactions
Peroxidation reaction with hydrogen peroxide

What are the applications of Application

Myosmine is a specific tobacco alkaloid

Definition

ChEBI: Myosmine is a member of the class of pyridines that is pyridine substituted by a 3,4-dihydro-2H-pyrrol-5-yl group at position 3. It is an alkaloid found in tobacco plants and exhibits genotoxic effects. It has a role as a plant metabolite, an EC 1.14.14.14 (aromatase) inhibitor and a mutagen. It is a pyrroline and a pyridine alkaloid.

Synthesis Reference(s)

Canadian Journal of Chemistry, 35, p. 651, 1957 DOI: 10.1139/v57-094
The Journal of Organic Chemistry, 37, p. 1635, 1972
Tetrahedron Letters, 8, p. 5185, 1967

References

Spath, Wenusch, Zajic., Ber., 69, 393 (1936)
Woodward, Eisner, Haines., ibid, 69, 7S7 (1936)
Spath, Wibaut, Kesztler., ibid, 71, 100 (1938)