174 



SCIENCE 



[N. S. Vol. XLII. No. 1075 



sonous depressor base, /?-iinino-azolyletliyl- 

 amine may be isolated from the intestinal 

 mucosa, and Bertbelot and Bertrand^" have 

 demonstrated that it is in all probability 

 formed in the intestinal canal from histidine 

 by the decarboxylating action of a bacillus 

 newly discovered by them which they have 

 named Bacillus aminopliilus intestinalis. 

 These investigators have shown that their ba- 

 cillus produces the base from histidine even 

 in the presence of 0.3 per cent, lactic acid, 

 unless, indeed, an excess of glucose be pres- 

 ent, in which ease only this is attacked, and 

 they have also made the interesting obser- 

 vation that rats, fed on a milk diet, are not 

 affected by either Proteus vulgaris or Ba- 

 cillus aminopliilus intestinalis when these 

 organisms are given separately, but that 

 when they are given simultaneously the 

 rats succumb to a diarrhea in from four to 

 eight days. 



Investigations on the pharmacological 

 behavior of j3-imino-azolylethylamine have 

 shown that it acts very powerfully on plain 

 muscle, stimulating the isolated uterus, for 

 example, to contraction in the almost un- 

 believable dilution of 1 : 250,000,000.*" The 

 muscular coats of the guinea-pig's bron- 

 chioles are so sensitive to its action that 

 large pigs are killed in a few minutes by 

 the intravenous injection of a half a milli- 

 gram. The death of the animal is due to 

 asphyxia produced by a spasm of the bron- 



tidme is submitted to the aetion of putrefactive 

 bacteria a considerable yield of |8-uiiiiio-azoly- 

 lethylamine is produced. Ztschr. f. physiol. Chem. 

 Vol. 64, p. 504, 1910. 



SB Compt. rend, de I'Acad. des Sciences, Vol. 

 154, pp. 1,643 and 1,826. See also Mallenby and 

 Twort, "On the Presence of j3-imino-azolyIethyla- 

 mine in the Intestinal Wall, with a Method of Iso- 

 lating a Bacillus from the Alimentary Canal which 

 Converts Histidine into this Substance," Jour, of 

 Physiol., 45, p. 53. 



40 See FriJhlich and Pick, Arch. f. Exp. Fatlwl. 

 u. Fharmakol., Vol. 71, p. 23, and Sugimoto, ibid., 

 Vol. 74, p. 27. 



chioles. Eecently investigators have been 

 much occupied in studying similar features 

 in the symptoms of the poisoning by large 

 doses of the base and those observed in ana- 

 phylactic shock (aetion on the circulation, 

 body temperature, respiration, etc.) and 

 some do not hesitate to affirm that the poi- 

 sons of anaphylactic shock must be put 

 into the same pharmacological class with 

 the proteinogenous bases that we have been 

 considering. 



We may now give the chemical formulas 

 that illustrate the various relationships 

 that have been discussed. 

 OH 



/\ OH 

 1. 



\/ 

 CH.OH.CH2NH.CH3 



Epinephrin, adrenaline, suprarenin, possibly de- 

 rived by decarboxylation from a still unknown 

 amino acid, dioxyphenyl-a-m6thylamino-|3-oxypro- 

 pionic acid, as suggested by M. Guggenheim. 

 Therap. Monatsh., XXVII., p. 508, 1913. 



OH OH 



,/\. OH ,-^\ OH 



~* I + CO2 



V \/ 



CH.0H.CH.NH.CH3 CH.OH.CH2NH.CH3 



I Epinephrin 



COOH 

 (Unknown amino-acid) 

 OH 



^- I I 



\/ 

 CHj.CHj.NH, 



p-hydroxyphenylethylamine, derived from p-hy- 

 droxyphenyl-o-amino-propionic acid, or tyrosine, as 

 follows : 

 OH OH 



/\ /\ 



II -* I I 



CHj. CH. NHjCOOH CHj. CHj. NH^ 



Tyrosine p-hydroxyphenylethylamine 



(Tyramine) 



/\ 



I I 



3. I I 



\y 



CH,.CH,NH, 



+ CO, 



