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

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 Y
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 Y
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:[1]
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

See also

• Catharanthine
• Nicotelline
• Pozanicline
• PHA-543,613

References

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.
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.