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
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:
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 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]

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.

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[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.

[pmid19601869-3] 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.

[pmid28844873-4] 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.

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Myosmine

Chemical synthesis

See also

References