BETAINE, TRIMETHYLAMINE 265 



Considerations of space will not permit more than the very 

 briefest reference to the chemistry of these substances. 



The compounds choline, muscarine, betaine, and neurine 

 are closely related, as may be seen from their formulae : — 



N(CH3)30H N(CH3)30H N(CH3)3. N(CH3)30H 



I I I >o I 



CHoCHgOH CH3CHO CH2CO/ CH=CH2 



Choline Muscarine Betaine Neurine 



the relationship to each other of the first three being that of 

 alcohol, aldehyde and acid anhydride.* 



Choline and muscarine occur in the toad-stool, Amanita 

 muscaria. Betaine and choline frequently occur together, as 

 for example in the germ of Hordeum sativum, Triticum sati- 

 vum, Vicia sativa, Lathyrus sativus, Gossypium kerbaceum, and 

 several other plants. Betaine alone occurs in the juice of the 

 beet f and in tubers of Helianthus tuberosus. Choline is far 

 more widely distributed, and occurs in seeds and fruits of a 

 very large number of plants, such as Pinus cembra, Areca 

 Catechu (nut), Cocos nucifera (endosperm"), Acorus calamus 

 (root), Fagus silvatica, Cannabis sativa and C. indica, Humulus 

 Lupulus, etc. 



Neurine does not occur in plants, but is produced in putre- 

 fying fish and meat. Muscarine and neurine are both very 

 poisonous, whereas choline is comparatively innocuous. 



All these substances are strong bases, and answer the gen- 

 eral reactions for alkaloids (which see). 



A few other bases of comparatively simple constitution 

 which occur in plants may here be mentioned. 



Trimethylamine, (CH3)3N, is a very volatile substance which 

 occurs in the seeds of Mercurialis annua and in the flowers of 

 CratcBgus Oxyacantha, Pyrus Aucuparia, and many other plants, 



* The name betaine is derived from the fact that this substance was first 

 obtained from the beetroot {Beta vulgaris). It is the anhydride of hydroxytri- 

 methylamino-acetic acid. 



N(CH3)3V 



-^ H.,0 I )0 



CH,CO/ 



N(CH3)3 oh; 



CHjCOOiH : 



The alkaloid stachydrine (see p. 257) is a derivative of this substance, 

 t For the preparation of betaine from this source, see " Ber. deut. chem. 

 Gesells.," 1912, 45, 2411. 



