Myosmine

Myosmine is an alkaloid found in tobacco[2] and other plants.[3] Chemically, it is closely related to nicotine. It inhibits aromatase sevenfold more potently than nicotine.[4] It also releases dopamine in adult but not adolescent rats.[5]

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
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
Hazards
GHS labelling:[1]
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).
Infobox references

See also

References
  1. "Myosmine". pubchem.ncbi.nlm.nih.gov. Retrieved 14 August 2023.
  2. C. Laszlo, K. Kaminski, H. Guan, M. Fatarova, J. Wei, A. Bergounioux, W. K. Schlage, S. Schorderet-Weber, P. A. Guy, N. V. Ivanov, K. Lamottke and J. Hoeng (Nov 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species", Molecules 2022, 27(22), 8105.
  3. 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.
  4. 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.
  5. 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.


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