TRANSACTIONS OF SECTION B. 583 



although they ascribe to it a different structure from the a- and /3-compounds it 

 may for the sake of uniformity be called y-methylmorphimethine. 



Working under the direction of Professor Knorr, of Jena, the author has 

 obtained a fourth isomer — 5-methylmorphimethine — by boiling the y-derivative 

 for some time with alcoholic potash, a method analogous to that used in preparing 

 the /3- from the n-form. 5-methylmorphimethine forms ■well-defined prismatic 

 crystals : it is sparingly soluble in ether, but easily in methyl and ethyl alcohols, 

 chloroform, benzene, ethyl acetate, and acetone. It melts at about 112° C, and 

 in methyl alcohol it gives a specific rotation of +256°. 



The methiodide of S-methylmorphimethine crystallises from water in rect- 

 angular plates, melting at 282° C. and giving the specific rotation + 151°. It 

 can also be prepared directly from the y-methiodide by boiling the latter for 

 some time with dilute caustic potash. A similar transformation of a- into 

 0-methiodide was eflfected by Hesse. 



The benzoate of the new base crystallises in fine needles, and in 99 per cent, 

 alcohol has a specific rotation of + 181°, as against + 41° for the y-derivative. 



The research is not yet finished, but the results already obtained support the 

 theory as to the existence of two asymmetric carbon atoms in the molecule of 

 morphine and its immediate derivatives. 



4. The Alkylation of Stigars. 

 By Thos. Purdie, F.E.S., and James C, Irvine, £,Sc., Ph.J). 



The method of alkylating hydroxyl groups by means of a mixture of silver 

 oxide and alkyl iodides does not appear directly applicable to aldoses or ketoses, 

 and results in oxidation and subsequent changes of some complexity. By means of 

 this reaction, however, the authors have succeeded in alkylating methyl glucoside 

 with the formation of tri-methylic and tetra-methylic methyl glucoside ethers, com- 

 pounds from which alkylated aldoses can presumably be obtained on hydrolysis. 



Tri-methylic methyl glucoside ether. — The methyl glucoside used in the pre- 

 paration was obtained by heating glucose in CII^OH solution with HCl for fifty 

 hours at 100°. The glucoside (melting-point 165°-167°) was dissolved in boiling 

 methyl alcohol, and a large excess of the alkylating mixture, in the proportion of 

 two molecules iodide to one of oxide, gradually added. After all action ceased, the 

 mixture was boiled under a condenser for over an hour, and filtered. 



On removal of the alcohol, the filtrate was extracted with ether, and after 

 drying' and evaporation, the neutral syrupy extract was distilled in vacuum from a 

 graphite bath. Au extremely thick colourless liquid passed over between 

 155°-157° under 13 mm. pressure, and after refractionation a sample gave on 

 analysis figures in close agreement with the calculated numbers for tri-methylic 

 methyl glucoside ether : 



CHOOIL . CHOOH, , CHOCH„ . CH . CHOCH, . CH.,OH. 



A molecular weight determination showed that no rupture of the molecule had 

 occurred, and the methoxyl content of the compound was confirmed by Zeisel 

 determinations. 



The higher fractions obtained in the vacuum distillation were extremely thick, 

 and the results of analyses showed these to consist of incompletely methylated 

 glucoside. 



Tri-methylic methyl glucoside is optically active, a o per cent, solution ia 

 alcohol showing a specific rotation of -t- 126'75° at 20°, whilst for the pure sub- 

 stance {a)-[)^^= + 129"27°. The compound is soluble in water, alcohol, ether, and 

 methyl iodide, and the aqueous solution has no action on Fehling's solution until 

 hydrolised with HCl, when the aldose produced in the reaction efl^eets ready 

 reduction. 



Tetra-methylic methyl glucoside. — Thjs compound was prepared by adding 



