This forms a potaasic derivative which with methyliodide yields 



CH . CH 

 11 11 



CH 



CH 3 



NCH 3 I 

 and this, when distilled with lime, gives 



CH - CH 



' 



N(CH 3 ) . CH 



^-pyridyl-N -methyl pyrrol, which can be converted into ^-pyridyl-N-methyl 

 pyrolidine (i-nicotine) by the addition of hydrogen. The racemic alkaloid thus 

 obtained may be resolved into its optically active components by the aid of 

 O^-tartaric acid when, ] -nicotine-d-tartrate chrystallizes out first. 



OCCURENCE 



In leaves of tobacco (Nicotiana Tabacum) and in the leaves of Macrophy|la 

 rustica and N. glutinusa. Occurs also in Pituri. According to Zeise and 

 Vohl and Eulenberg it is not present in tobacco smoke, but Heubel obtained 

 evidence of its presence therein. 



PREPARATION 



Tobacco leaves (10 parts) are soaked in water 24 hours, and the mixture 

 heated to 100 by steam. The aqueous extract is mixed with lime (1 part) 

 and distilled. The distillate is neutralized by oxalic acid and evaporated to a 

 thin syrup. Addition of concentrated KOH now separates the base, which is 

 rectified in a current of hydrogen. 



PROPERTIES 



Colorless liquid, not frozen at -IQo . Smells like tobacco, unless it is quite 

 pure. It is very hygroscopic. Mixes with water, developing heat, and is very 

 soluble. It has a disagreeable odor and burning taste. A very violent poison. 

 Leavorotatory. Optical activity of its aqueous solution varies greatly with 

 concentration in a 4 percent, solution, [d] D = -77 at 20 : in a .88 percent. 

 solution [d] D = -79. Solutions of salts of nicotine are dextrorotatary. Nic- 

 otine turns brown on exposure to air and light. Its solutions are strongly al- 

 kaline. Its very soluble in water, alcohol, ether, terpenes and fatty oils. At 

 100 it dissolves 10 percent, of sulphur, but on cooling it separates again 

 Ether extracts it from aqueous solutions. KOH separates it from aqueous so- 

 lutions. 



