- 4 - 
Analyses indicated tl^e formula C-jQH^^Ng. It formed a picrate, 
C-Lo2T^4N2;2CgH2(OH)(w02)3, melting point 205-207°, and a picrolonate, 
melting point 235-237'^.. Silicot'ongstic abid gave a ^hite amorpho'-is 
precipitate with even ver;;-- dilute solutions of the base. 
Orekhov and I'enshikov (98) in 1931 published the first of a series 
of papers on the alkaloids of Ana.basi s aphylla L. 
Percolation of the dried plant with 2 percent of ammonia in 95- 
percei.t alcohol, evaporation to dryness, e:?traction with 10-percent liydro- 
chloric acid, precipitation with 50-percent scdi-um hydroxide, extraction 
with . ether, drying with potassium carbonate, and evaporation yielded 
2.33 ; 'ercent of a thick oil, separated by vacuum distillation (12 mni. 
pressure) into 85 percent of a fraction boiling at 13.5-6.5° and 15 percent 
arouni. 200°. The lower-boiling fraction could be separated by benzoyla- 
tion, by the action of nitric acid, or by vacuum distillation into a 
tertiary amine, C]lo^'^19^-^» ^^a-ving all the properties of the lupinine 
obtaii ed from Lupinus luteus , and a secondary amine, CiQHi4iJ2» designated 
anabasLne, which with potassrom permanganate gave nicotinic acid in good 
yield, and on dehydrogenation, either bj'- heating with silver acetate or 
by ref -uxing with zinc dust, lost 5 hydrogen atoms, forming a bipyridyl, 
boilini point 293-4° (picrate, melting point 151-2°), thought to be iden- 
tiiJBl wl th the alpha, beta' -bipyridyl of Slcraup and Yortmann , boiling point 
295-6° '^picrate, melting point 149.5^). Anabasine is, therefore, very 
probably' alpha-piperidyl-beta-pyridine, which, however, is certainly dif- 
ferent from Pictet's nicotimine for which he suggested the same structure. 
Anabasine, prepared from the benzoyl derivative (m. 82-33) and 
hydJTOchloric acid (d. 1.19) in sealed tubes at 100° was reported to have 
the following properties: ^^qq21So, d|g 1.0455, n^^ 1.5430, alpha^]§^= 
-82.20*-'. Anabasine reacts strongly al.caline , is quite difficultly 
volatile with steam, stable for nours towards potassium permanganate in 
sulphuric acid; the hydrochloride salt immediately deliquesces in the air, 
and is dextrorotary. 
-he chemistry of anabasine has been studied by the Russian chemists 
Crekhov and associates (79, 80, 81, 82, 88, 90, 91, 92, 93,94, 95, 96, 97, 
98, 99, 100, 101, 102, 103, 104, 105, 106), Katznel'son and associates 
(47, 48, 49, 50, 53, 54, 55, 55), and ilenshikov (78); and by the German 
chemists Bhrenstein (22) and 17enusch (158, 159); and the reader is re- 
ferred to their publications for detailed information on this subject. 
Other alkaloids of Anabasis aphylla 
Orekhov and iienshikov (99) in 1931 reported isolating additional 
alkaloids from Anabasis aphylla , called aphylline and aphyllidine. In 
1937 Orkhov (95) proposed a structure for aphyllidine, '^i^^'^'^^-2'^ , melt- 
ing point 112-13°, alphan 5.5, and also for aphylline, ^\^^2^2'^ ^ melting 
point 162-4°, alpha^ 54.5, which is the corresponding saturated compound. 
Synthesis of Anabasine 
Anabasine was s^aithesized before it was found in nature, a reversal 
