MYOSMINE Chemical Properties

Melting point:

42-44°C

Boiling point:

82-83°C 0,5mm

Density 

1.12±0.1 g/cm3(Predicted)

Flash point:

82-83°C/0.5mm

storage temp. 

2-8°C

solubility 

Methanol (Slightly), Water (Sparingly)

pka

pK1:5.26 (25°C)

form 

Solid

color 

Light Beige to Dark Yellow

BRN 

119254

Stability:

Moisture, Temperature Sensitive

LogP

0.730 (est)

CAS DataBase Reference

532-12-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UT7660000

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

29399990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

MYOSMINE Usage And Synthesis

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

Uses

mitogen

Uses

Tobacco alkaloid

Reactant for:
Nitrosation reactions
Peroxidation reaction with hydrogen peroxide

Uses

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

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)

MYOSMINE(532-12-7)Related Product Information

• O-MYOSMINE
• NICOTINE IMP. D (EP): 3-(4,5-DIHYDRO-3H-PYRROL-2-YL)-PYRIDINE (MYOSMINE)
• MYOSMINE-D4
• MYOSMINE(REAGENT / STANDARD GRADE)
• MYOSMINE, [PYRIDINE-5-3H]- 5-30 CI(0.185-1.11 TBQ)/MMOL, DELIVERED >= 96% PURE WITH HPLC RADIOCHROMATOGRAM
• MYOSMINE
• MYOSMINE-2,4,5,6-D4 (PYRIDINE-D4),MYOSMINE-2,4,5,6-D4
• 6-Methyl Myosmine
• MYOSMINE, [PYRIDINE-5-3H]-
• 3-(4,5-DIHYDRO-3H-PYRROL-2-YL)-QUINOLINE
• 2-Methyl Myosmine
• 5-METHYLMYOSMINE