Myosmine

Myosmine
Names
	Preferred IUPAC name 3-(3,4-Dihydro-2H-pyrrol-5-yl)pyridine
	Other names 3-(1-Pyrrolin-2-yl)pyridine
Identifiers
CAS Number	532-12-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:7051;
ChEMBL	ChEMBL423429;
ChemSpider	391011;
ECHA InfoCard	100.165.015
EC Number	637-297-7;
KEGG	C10160;
PubChem CID	442649;
UNII	9O0A545W4L ;
CompTox Dashboard (EPA)	DTXSID70891866 ;
	InChI 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;
	SMILES n1cccc(c1)/C2=N/CCC2;
Properties
Chemical formula	C9H10N2
Molar mass	146.193 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	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 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]

References

^ "Myosmine". pubchem.ncbi.nlm.nih.gov. Retrieved 14 August 2023.
^ Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, Schlage WK, Schorderet-Weber S, Guy PA, Ivanov NV, Lamottke K, Hoeng J (November 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species". Molecules. 27 (22): 8105. doi:10.3390/molecules27228105. PMC 9694777. PMID 36432206.
^ 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.

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[1] "Myosmine". pubchem.ncbi.nlm.nih.gov. Retrieved 14 August 2023.

[2] Laszlo C, Kaminski K, Guan H, Fatarova M, Wei J, Bergounioux A, Schlage WK, Schorderet-Weber S, Guy PA, Ivanov NV, Lamottke K, Hoeng J (November 2022). "Fractionation and Extraction Optimization of Potentially Valuable Compounds and Their Profiling in Six Varieties of Two Nicotiana Species". Molecules. 27 (22): 8105. doi:10.3390/molecules27228105. PMC 9694777. PMID 36432206.

[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.

[pmid19601869-4] 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.

[pmid28844873-5] 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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See also

References