34 LECTURE II. 



other change. This is, for example, the case with substances containing 

 an hydroxyl group. Thus, trimethyl carbinol introduced into the system 

 is eliminated in the urine as a conjugated glucuronic acid: 1 



(CH 3 ) 3 . COH + C 6 H 10 7 = (CH 3 ) 3 . CO.C 6 H 9 O 6 + H 2 



Many compounds, however, are not chemically suitable for coupling 

 with glucuronic acid. They are prepared for combination by the action 

 of the animal body either by reduction, by oxidation, by hydration, or by 

 the two last-named processes acting together. Thus, for example, chloral 

 hydrate 2 and butylchloral hydrate 3 are reduced. The former is changed 

 into trichlorethyl alcohol, and this combines with glucuronic acid, the 

 conjugated acid being eliminated in the urine. The compound formed is 

 known as urochloralic acid: 



C1 3 C . CH + 2 H = C1 3 C . CH 2 OH + H 2 O, 



N OH 

 C1 3 C . CH 2 OH + C 6 H 10 7 = C1 3 C . CH 2 O . C 6 H 9 O 6 + H 2 O. 



A preliminary oxidation takes place in the case of o-nitrotoluol 4 it being 

 changed in the organism of the dog to nitrobenzyl alcohol: 



NO 2 . C 6 H 4 . CH 3 + O = NO 2 . C 6 H 4 . CH 2 OH, 

 NO 2 . C 6 H 4 CH 2 OH + C 6 Hi 7 = NO 2 . C 6 H 4 . CH 2 O . C 6 H 9 6 + H 2 O. 



Many camphor varieties undergo a similar preliminary oxidation. 



In other cases the animal organism causes the poisonous substance to 

 take on water, and oxidation may take place simultaneously. An example 

 of this is found in the transformation of thujone into thujone hydrate, 5 

 which then unites with glucuronic acid: 



OCi Hi 7 OH + C 6 H 10 O 7 = OCi H 17 . C 6 H 9 O 6 + H 2 0. 

 Camphene 6 is changed into camphene glycol: 



Ci H 16 + O + H 2 = HO . C 10 H 16 . OH. 



As the above equations show, the fundamental principle of the coupling 

 is in all cases the same, except that sometimes the poison can unite directly 

 with the glucuronic acid (or glucose see above) , while otherwise this 



Thierfelder and von Mering: Z. physiol. Chem. 9, 511 (1885). 



von Mering: ibid. 6, 480 (1882). von Mering and Musculus: Ber. 8, 662 (1875). 



Kiilz: Pfliiger's Arch. 28, 506 (1882); 33, 221 (1883). 



Jaff6: Z. physiol. Chem. 2, 47 (1878-79), and Ber. 12, 1092 (1878). 



Emil Fromm and Hermann Hildebrandt: Z physiol. Chem. 33, 579 (1901). 



Fromm, Hildebrandt, and Clemens: ibid. 37, 189 (1902-03). 



