WHERRY AND YANOVSKY: MORPHINE) DERIVATIVES 507 



The alkaloid liberated from a commercial sample of the hydro- 

 chloride was recrystallized from absolute methyl alcohol until 

 its specific rotation remained the same in two consecutive crys- 

 tallizations. The final value for a i% solution in methyl alco- 

 hol was [af^° = — i3i-7°- The usually recommended recrys- 

 tallization from amyl alcohol was found to be less satisfactory. 



The crystals finally obtained from methyl alcohol, which at- 

 tained a diameter of about i mm., were measured on a Gold- 

 schmidt two-circle goniometer, with the results presented in 

 table I. The orientation adopted is that of Schabus, but the 

 steeper dome is taken as the unit form, giving a value dift'erent 

 from his for axis c. 



The essential agreement between the measurements of pre- 

 ceding authors and those here reported indicates that morphine 

 normally crystallizes, as monohydrate, in a single form, there 

 being no evidence of polymorphism. 



Partial optical descriptions of this substance have been pub- 

 lished by Lang,- by Kley'' and by Wright^ but there are con- 

 siderable discrepancies among their results. On examining our 

 material by the immersion method, using liquids made up 

 chiefly of a petroleum oil, in which the alkaloid is but slightly 

 soluble, the data of Lang and of Wright were confirmed for the 

 most part, and Kley's value for one refractive index could be 

 explained as a mean between the largest and smallest indices, 

 while his axial angle must be 2 V. The data obtained were: 



Refractive indices [ d ] « = 1-580, — 1.625, T = 1-645, 

 7 — <x = 0.065, a-11 =^ 0-005. Index i3 is usually shown length- 

 wise of the rods, and one of the other, or intermediate, values, 

 crosswise; the optic axial plane is perpendicular to the elongation 

 of the crystals; axial angle 2E is very large, approximately 125°; 

 sign — ; dispersion strong with 2Er>2Ev- 



CODEINE, morphine; methyl ester, Ci8H2iN03 



This alkaloid crystallizes in both anhydrous and hydrous forms. 

 The former was obtained from carbon disulfide solution and 



* Loc. cit. 



' Zeitschr. anal. Chem. 43: 164. 1904. 



^ Journ. Amer. Chem. Soc. 38: 1655. 1916. 



