468 POISONS : THEIR EFFECTS AND DETECTION. [§ 598. 
Barger and Dale isolated it from the commercial dialysed extract 
of commerce, using Kutscher’s elaborate method for the isolation of 
bases from meat extract (Barger and Dale, J.C.S., T., 1910). It is 
of intense physiological activity. The synthetic base is in commerce 
under the name of ergamine. The picrate forms dark yellow rhombic 
plates, m.p. 234°-235°; the picrolonate melts at 261°. 
Amino-butylene-guanidine (Agmatine), NH 2 CNH.NH.(CH 2 ) 4 NH 2 , 
which differs from arginine only by C0 2 , was discovered by Albrecht 
Kossel ( Text. Phys. Chem., 1910) by treating herring spawn with sulphuric 
acid at four atmospheres pressure. The same chemist has found it in 
ergot. It can be synthetised by the direct action of an aqueous solution 
of cyanamide on tetra-methylene-diamine. This base has also an action 
on the uterus, but is not in commerce. 
Acetylcholine has been added to the active principles of ergot 
(A. J. Ewins, Biochem. Journ,. 1914). 
§ 598. Ergothioneine, C 9 H 15 0 2 N 3 S,2H 2 0, is a base discovered in 
ergot by C. Tauret (Compt. Rend., 1909), and investigated since by 
Barger and Ewins ( J.C.S ., T., 1911) ; it is a betaine related to his¬ 
tidine. On oxidation by ferric chloride it is transformed into trimethyl 
histidine. It occurs in ergot to the extent of 0-1 per cent. It crystallises 
in colourless clinorhombic lamellse, m.p. 290°. Rotation [a] D +110°. 
Barger and Ewins have identified it as /3-2-thiolglyoxaline-4 (or 5)- 
propiobetaine 
CH.NH 
II ^C.SH 
C - N 
ch 2 
CH.N.Me 3 
CO-O 
On boiling with strong potash (50 per cent.), trimethylamine is evolved. 
The residue in the distilling flask, acidified by a mineral acid, precipitates 
yellow amorphous /3-2-thiolglyoxaline-4-acrylic acid. This substance 
is moderately soluble in pyridine, but almost insoluble in other ordinary 
organic solvents. On crystallising the acid from a solution in dilute soda 
and acidifying, the m.p. is above 275°. 
On oxidising this acid with nitric acid, the sulphur atom is removed 
and /3-glyoxaline-4 (or 5)-acrylic acid is formed, which may be reduced 
by sodium and alcohol to j3-glyoxaline-4 (or 5)-propionic acid. 
Ergothioneine forms a remarkable compound with iodine—steel- 
blue, grey, or black crystals mixed with iodine. Ergothioneine is 
