Myosmine
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| Names | |
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| Preferred IUPAC name
3-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine | |
| Other names
3-(1-Pyrrolin-2-yl)pyridine | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.165.015 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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:[1] | |
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| 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).
Infobox references | |
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.[2] Chemically, it is closely related to nicotine. It inhibits aromatase sevenfold more potently than nicotine.[3] It also releases dopamine in adult but not adolescent rats.[4]
Myosmine is a precursor to nicotinic acid.[5]
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.[6]
See also
References
- ↑ "Myosmine". pubchem.ncbi.nlm.nih.gov. Retrieved 14 August 2023.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.