BETAINES 47 



thiolglyoxalines are intermediate products in the chief method for 

 synthesising glyoxalines, due to Gabriel. The sulphur of ergothioneine 

 behaves very differently from that in cystine ; it is not removed by 

 alkalies and ergothioneine, therefore does not blacken lead hydroxide 

 solution on boiling. . On the other hand the sulphur atom is much 

 more readily attacked by weak oxidising agents such as ferric chloride. 



Bearing this in mind we may perhaps hope to isolate ergothioneine 

 or similar sulphur compounds from sources other than ergot. 



The physiological activity of ergothioneine is slight and it does 

 not make any significant contribution to the action of ergot. 



Hypaphorine, Trimethyltryptophane, C 14 H 18 O 2 N 3 . 



Hypaphorine is the betaine of tryptophane and has the constitution 



CH 

 CH f ^ - C CH, . CH . CO 



CH L "cH 



\/C\/ N(CH.)..O 



CH NH 



It was discovered by Greshoff [1898] in the seeds of Erythrina 

 Hypaphorus, Boerl., a tree grown for the sake of its shade in the coffee 

 plantations of Eastern Java, and known locally as " dadap minjak ". 

 The constitution of hypaphorine has been investigated by Van Rom- 

 burgh [1911]. On heating with concentrated aqueous potassium 

 hydroxide indole and trimethylamine result. The constitution was, 

 however, determined by the synthesis from tryptophane (Van Rom- 

 burgh and Barger [1911]). On heating tryptophane in methyl 

 alcoholic solution with sodium hydroxide and methyl iodide the quater- 

 nary iodide of methyl-a-trimethylamino--indolepropionate is formed 



CH 

 CH ^ - C-^CH, . CH . COOCH, 



CH \A/ CH N(CH 8 ),I 



CH NH 



and this, on warming with dilute alkali, yields a substance identical 

 with the naturally occurring hypaphorine. 



Physiological Action of Hypaphorine. The substance has hardly any 

 action on rodents and pigeons; thus intravenous doses of 0-5-1 grm. 

 do not affect rabbits and the unchanged substance is rapidly secreted 

 in the urine. In frogs, however, doses of 12-1 5 mg. produce increased 

 reflex irritability and tetanus, lasting for days in non-fatal cases. 



Trigonelline, C 7 H 7 O 2 N. 



This substance, the betaine of nicotinic acid, is not derived from a 

 protein fission product ; it contains a pyridine nucleus and is there- 



