Solanidine is a poisonous steroidal alkaloid chemical compound that occurs in plants of the family Solanaceae, such as potato and Solanum americanum.
[4] Solanidine is the hydrolyzed form[4] of several naturally occurring compounds all found in the Solanaceae family, such as glycoalkaloids, α-solanine and α-chaconine.
The theorized biosynthetic route for the creation of Solanidine proposed in 1977 within the Solanaceae family was thought to be derived from cholesterol to the SA aglycone.
[10][11] Symptoms of cholinesterase inhibition include insomnia, nausea and vomiting, accidental injury, headache, dizziness, bradycardia, hypotension, ecchymosis, and sleep disturbance.
Since consumption of potatoes is so common, solanidine can be used as a biomarker when studying CYP2D6 drug-drug interactions and improve CYP2D6 activity prediction.
The advantage of this reagent and solvent system was the ease of use and the selective formation of iminium salt 2, which spontaneously isomerized to enamine 3 (94%).
[18][19] Only in case of acetylated solanidine the von Braun reaction gave the E ring-opened product in 78% yield.
Treatment of α-bromine with KOAc gave in good yield the β-diacetate, which could be reduced with red-Al in benzene.