Myosmine

Myosmine
Skeletal formula of myosmine
Ball-and-stick model of the myosmine molecule
Names
Preferred IUPAC name
3-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine
Other names
3-(1-Pyrrolin-2-yl)pyridine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.165.015 Edit this at Wikidata
EC Number
  • 637-297-7
KEGG
UNII
  • InChI=1S/C9H10N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7H,2,4,6H2
    Key: DPNGWXJMIILTBS-UHFFFAOYSA-N
  • n1cccc(c1)/C2=N/CCC2
Properties
C9H10N2
Molar mass 146.193 g·mol−1
Appearance colorless solid
Melting point 44 °C (111 °F; 317 K)
Boiling point 77 °C (171 °F; 350 K) 0.15 mm Hg
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Related compounds
Related compounds
 Isomyosamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Myosmine is an alkaloid with the formula NC5H4−C4H6N. It is structurally and biosynthetically related to nicotine, being also found in tobacco and several other plants. Chemically, it is closely related to nicotine. It inhibits aromatase sevenfold more potently than nicotine. It also releases dopamine in adult but not adolescent rats.

Myosmine is a precursor to nicotinic acid.

Chemical synthesis

Myosmin can be prepared in the laboratory from 3-lithiopyridine via condensation with cyclobutanone to give the pyridyl-cyclobutanol. Reaction of the latter tertiary alcohol with hydrazoic acid under conditions for the Schmidt reaction gives myosmine. Reduction of the imine group in myosmin with sodium cyanoborohydride affords nornicotine.

See also

References

  1. ↑ "Myosmine". pubchem.ncbi.nlm.nih.gov. Retrieved 14 August 2023.
  2. ↑ Tyroller, Stefan; Zwickenpflug, Wolfgang; Richter, Elmar (2002). "New Sources of Dietary Myosmine Uptake from Cereals, Fruits, Vegetables, and Milk". Journal of Agricultural and Food Chemistry. 50 (17): 4909–15. doi:10.1021/jf020281p. PMID 12166981.
  3. ↑ Doering IL, Richter E (April 2009). "Inhibition of human aromatase by myosmine". Drug Metabolism Letters. 3 (2): 83–6. doi:10.2174/187231209788654045. PMID 19601869.
  4. ↑ Marusich JA, Darna M, Wilson AG, Denehy ED, Ebben A, Deaciuc AG, Dwoskin LP, Bardo MT, Lefever TW, Wiley JL, Reissig CJ, Jackson KJ (November 2017). "Tobacco's minor alkaloids: Effects on place conditioning and nucleus accumbens dopamine release in adult and adolescent rats". European Journal of Pharmacology. 814: 196–206. doi:10.1016/j.ejphar.2017.08.029. PMC 6563910. PMID 28844873.
  5. ↑ Zwickenpflug, Wolfgang; Hornung, Florian; Hollaus, Alexandra; Oswald, Michaela S.; Chioato, Zoé; Gudermann, Thomas; Högg, Christof (2024). "Biosynthesis of vitamin B3 and NAD+: Incubating HepG2 cells with the alkaloid myosmine". Journal of the Science of Food and Agriculture. 104 (11): 6844–6854. doi:10.1002/jsfa.13513. PMID 38578648.
  6. ↑ Alberici, Gilles F.; Andrieux, Jean; Adam, Gérard; Plat, Michel M. (1983). "Synthesis of tobacco alkaloids via tertiary azides". Tetrahedron Letters. 24 (18): 1937–1940. doi:10.1016/S0040-4039(00)81810-9.