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ADRENALIN. 379
The synthetically prepared adrenalin is optically inactive r/-/-adrcnalin,
while that from the adrenals is optically active /-adrenalin. FLACHEB has
divided the racemic adrenalin into the two optically active components,
and the identity of the so-obtained synthetical adrenalin with the natural
has been shown by Abderhalden and Fr. Muller.1
These last inves-
tigators also found that the /-adrenalin had at least 15 times as strong
an action upon the blood-pressure as the (/-adrenalin, and later Abder-
halden with Thies and Slavu found that the /-adrenalin had also in
other respects a much stronger action than d-adrenalin.
Adrenalin crystallizes in masses of needles or rhombic leaves. It is
soluble in water, and can be precipitated from its solution by ammonia
as a crystalline substance. Its aqueous solution containing hydrochloric
acid is levorotatory : (c*) D = —50.72° (Abderhalden and Guggenheim 2
).
On heating adrenalin it turns yellowish-brown at about 205° and decom-
poses at about 218° C. Its solution turns emerald green with ferric chlor-
ide in acid solution and carmine red in alkaline solution. Adrenalin
reduces Fehling’s solution and ammoniacal silver solution.
Among the reactions for adrenalin in solution we must especially
mention the red coloration which is obtained on the addition of an oxidizing
medium such as iodine or bi-iodate and dilute phosphoric acid and warm-
ing (Frankel and Allers), or of mercuric chloride in the presence of a
catalyst such as the lime salts in tap-water (Comesatti). These reactions
are extremely delicate, 1 : 1000000-2000000. A still more delicate reaction
(1:5000000) is the one suggested by Ewins,3
namely a characteristic
red coloration is obtained on adding a 0.1 per cent solution of potassium
persulphate and wr
arming gently in a boiling water-bath.
As above stated, it has been considered for some time that the color
of the skin in Addison’s disease was connected with the adrenals or their
chromogen. We know nothing positive in regard to this relation,
but it is nevertheless of interest that pigments, and finally melanins or
at least dark-brown substances, can be produced from adrenalin by the
action of enzymes. Neuberg has brought about such melanin forma-
tion by the extract from the metastases of a melanoma of the adrenals
and also with the extract of the ink-sac of the sepia, and Abderhalden
and Guggenheim 4
with tyrosinase. This would indicate a close relation
1
Flacher, Zeitschr. f. physiol. Chem., 58; Abderhalden and Franz Muller, ibid.
58; with Thies, ibid., 59; with Slavu, ibid., 59; with Kautsch and Muller, ibid., 61 and
62; see also Frohlich, Centralbl. f. physiol., 23 and Waterman, Zeitschr. f. physiol.
Chem., 63.
2
Zeitschr. f. physiol. Chem., 57.
* Frankel and Allers, Bioch. Zeitschr., 18; Comesatti, Munch, med. Wochenschr.
1908 and Physiol. Centralbl., 23; Ewins, Journ. of Physiol., 40.
4
Neuberg, Bioch. Zeitschr., 8; Abderhalden and Guggenheim, Zeitschr. f. physiol.
Chem., 57.
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