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Myosmine

In stock
Catalog No.
C5707
agonist at neuronal nicotinic acetylcholine receptors
Grouped product items
SizePriceStock Qty
100mg
$64.00
In stock
250mg
$148.00
In stock
500mg
$252.00
In stock

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Background

Myosmine is a minor tobacco alkaloid that is structurally related to nicotine [1][3][4].

Myosmine is a specific tobacco alkaloid. It is found in a variety of other plants such as maize, rice, wheat flour, millet, potato, and milk and also cocoa, popcorn, tomato, carrot, pineapple, kiwi, and apples. Myosmine is easily nitrosated, yielding 4-hy-droxy-1-(3-pyridyl)-1-butanone (HPB) and a DNA adduct identical to the esophageal tobacco carcinogen N-nitrosonornicotine [2][4].

Myosmine is a minor tobacco alkaloid that is structurally related to nicotine. Nicotine is the addictive active ingredient in tobacco smoke that acts as an agonist at neuronal nicotinic acetylcholine receptors with Ki values of 480.69 and 11.13 nM for α3β4 and α4β2 subtypes, respectively [2]. Myosmine weakly binds to a4β2 nACh receptors with Ki value of 3.3 μM [3].

In rats treated with combinations of myosmine and NaNO2, no evidence showed the production of HPB-releasing Hb and DNA adducts, suggesting that exposure to dietary myosmine couldn’t lead to HPB-releasing DNA or Hb adducts in humans [5].

References:
[1].  Tyroller S, Zwickenpflug W, Richter E. New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. J Agric Food Chem. 2002 Aug 14;50(17):4909-15.
[2].  Zaveri N, Jiang F, Olsen C, et al. Novel α3β4 nicotinic acetylcholine receptor-selective ligands. Discovery, structure-activity studies, and pharmacological evaluation. J Med Chem. 2010 Nov 25;53(22):8187-91.
[3].  Ferretti G1, Dukat M, Giannella M, et al. Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors. Bioorg Med Chem Lett. 2003 Feb 24;13(4):733-5.
[4].  Zwickenpflug W, Tyroller S, Richter E. Metabolism of myosmine in Wistar rats. Drug Metab Dispos. 2005 Nov;33(11):1648-56.
[5].  Hecht SS, Han S, Kenney PM, et al. Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats. Chem Res Toxicol. 2007 Mar;20(3):543-9.

Chemical Properties

StorageStore at -20°C
M.Wt146.2
Cas No.532-12-7
FormulaC9H10N2
Solubility≥8.5mg/mL in DMSO
Chemical Name3-(3,4-dihydro-2H-pyrrol-5-yl)-pyridine
SDFDownload SDF
Canonical SMILESC1(C2=NCCC2)=CC=CN=C1
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

Myosmine