ERGOT OF RYE. 
595 "597-1 
Ergotinine melts at 229° and gives a sublimate (ergotoxine also) 
of isobutyril - formamide, (CH 3 ) 2 CH.CO.CO.NH. One part at 10° 
dissolves in 26 parts acetone; in boiling alcohol, 1 part dissolves 
in 52 parts ; in boiling benzene, 1 in 77 ; at 18°, 1 part dissolves in 91 
parts of ethyl acetate, in 292 parts of ethyl alcohol, and in 1020 parts of 
absolute ether. The rotation in acetone is [a] D +367°; in ethyl 
acetate, +363°; in chloroform, +396°. Ergotinine contains a molecule 
of water less than ergotoxine, and is the lactone of ergotoxine (Barger 
and Ewins, J.C.S., T., 1910). 
§ 595. Ergotoxine, C 35 H 41 0 6 N 5 .—This substance is not crystallisable, 
but forms crystallisable salts, the phosphate being the easiest to obtain 
in this form. The base is a light white powder, softening at 155° and 
melting at 162°-164°. Barger and Carr found the rotation in alcoholic 
solution to vary much, [«] D +0 # 6° to + 44*5°, possibly from racemisation. 
Both ergotinine and ergotoxine are precipitated by general alkaloidal 
reagents : potassium mercuric iodide precipitates 1 part ergotinine in 
1 million parts of water, ergotoxine in 2 million parts of the solvent. 
Ergotoxine can be transformed into ergotinine by boiling for some 
time with methyl alcohol, or by treatment with acetic anhydride. 
§ 596. Hydroxy-phenyl-ethyl-amine, OH.C 6 H 4 .CH 2 .CH 2 NH 2 (Tyra- 
mine), was isolated from putrid meat by Barger and Walpole ( Journ . 
Physiol., 1909), and is one of the products of the action of bacteria on 
tyrosine. Barger isolated the same substance from ergot by taking ad¬ 
vantage of its slight solubility in ether; the amount in ergot appears 
to be small—from *01 to 1 per cent. Barger ( J.C.S. , T., 1909) 
synthetised the base by the reduction of p-hydroxy-phenyl-aceto-nitrile; 
but it is obtained in better yield by the action of nitromethane on 
anisaldehyde forming CH 3 O.C 6 H 4 .CH.CH.N0 2 . This is reduced to the 
amine and the process completed by demethylation of the methoxy 
group, p-hydroxy-phenyl-amine occurs in hexagonal leaflets, m.p. 161°. 
It forms a N-monobenzoyl derivative, m.p. 162°; a dibenzoyl derivative, 
m.p. 170°; and a picrate (short prisms), m.p.200°. The base gives Millons’s 
and Morner’s reaction for tyrosine. It is soluble in 95 parts of water at 
15°, in 10 parts of boiling alcohol, and very slightly in ether. 
§ 597. 4-/3-Amino-ethyl-glyoxaline (/3-imino-azolyl-ethyl-amine) 
(Ergamine).—This base is closely related to histidine, and has been 
made synthetically thus :— 
N - C.CH 2 .CH 2 
S 
CH 
\ 
NH-CH NH 2 
4 -^-amino-ethy] -glyoxaline. 
N - C.CH 2 .CH.COOH 
s 
CH 
\ 
NH-CH NH 2 
Histidine. 
CH.COOH of histidine, replaced by CH 2 , gives the base. 
