TRANSACTIONS OF SECTION B. 849 



Acetic acid dissolves the brown substance, carbon dioxide being evolved. The 

 product on evaporation leaves a clear, glassy substance. 



In some later experiments the end of the ammonia action was considered to be 

 reached when the brown mass ceased to gain weight after exposing to dry 

 ammonia gas (nearly three months). 



Nitrogen determinations in this sample gave 21-2 per cent, and 21-46 per cent. 

 Some earlier samples contained only about 20 per cent. 



The carbon and hydrogen determinations are very unsatisfactory. Mean of 

 several carbon 21-5, hydrogen 3-5. They show a slight loss of carbon and gain of 

 hydrogen compared to the original gun-cotton. There is evidently an increase 

 of about 7 per cent, in the nitrogen. Possibly a further study of the acetyl com- 

 pound of this product may throw some light on the reaction. 



The nitrates from starch, mannitol, sugars, are also affected in a similar manner 

 by ammonia. Glycerol nitrate (nitro-glycerine) is not affected eitlier by gaseous 

 ammonia at 100° or by standing under strong ammonia solution for twelve 

 months. 



Methyl and ethyl, amine, and aniline act upon gun-cotton in a similar but less 

 energetic manner than ammonia. 



The subject is being continued. 



10. On Nitroso-pinene. By J. A. Smythe. 



By the reduction of nitroso-pinene (CjoHj^NO) with zinc in acetic acid 

 solution, there is formed, besides pinylamine, a new isomeric camphor (CigHj^O) 

 called pinocamphone. 



The boiling-point of pinocamphone is 211°-21.3°. Pinocamphone oxime melts 

 at 86°-87°. Pinocamphone semicarbazone melts at 208°. Reduction of ketoue 

 with sodium gives an isomeric borneol, OjoHi^O (pinocampheole), which boils at 

 218°-219°. The phenylurethane of pinocampheole melts at 98°. Pinocampheole 

 and zinc chloride yield cymene. Pinocamphone is the first synthetic camphor, the 

 oxime of which in treatment with dehydrating agents gives a nitrile. Oxidation of 

 pinocamphone yields a mixture of fatty acids. The reduction of bromnitroso-pinene 

 (CjoHijNOBrj) with zinc in acetic acid solution yields, not pinylamine and 

 pinocamphone, but an unknown base and bihydrocarvone. 



These results can only be satisfactorily explained on the assumption of 

 Wagner's formula for pinene. 



11. The Constitution of O.njcannahin. By T. B. Wood, M.A., W. T. IS". 

 Spivey, AI.A., and T H. Easterfield, M.A., Ph.D. 



Oxycannahin is a yellowish-white crystalline compound obtained by Bolas and 

 Francis in 1871 by the oxidation of pharmaceutical extract of hemp with nitric 

 acid. It has hitherto possessed little interest, since it was not known from what 

 naturally occurring compound the oxycannabin was derived, or what its chemical 

 xelationships were. 



The authors have found that that portion of hemp resin which boils at about 

 400* 0. contains two compounds ; one of these yields a crystalline acetvl derivative, 

 and has the formula C._,iH„uO.,. Cold fuming nitric acid converts" this into a 

 crystalline trinitro compound <^'nHo3(N0„)A. which yields characteristic salts, 

 and which, by the action of hot fuming nitric acid, yields ' Oxycannabin,' together 

 with caproic, valeric, and butyric acids. 



The formula ascribed by Bolas and Francis to oxycannabin was CoH.oN^O^ ; 

 in reality it has the formula OjJIjjNOj, which has 'nearly the same 'percentage 

 composition. It is a lactone, and yields salts of the type O^HioNOsM'. Upon 

 reduction it yields an amido-lactone C,iH„CNn.,)0,, from which, by Sandmeyer's 

 reaction, a crystalline iodo-lactone, CnHnIO^, has been obtained. The iodo-lactone, 

 when treated in alkaline solution with sodium amalgam, is reduced to the parent 

 cannabino-lactone, CiiH,.,0._,, a colourless liquid boiling at 290° C. 



1898. " 3l 



