The infrared spectra of a number of secor~dary bases and of their salts have been examined. 'l'he spectra of the salts differ from those of the corresponding bases in containing several absorption bands that are absent fro111 the latter.

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Some diarylpropanoid (bis-C6-C,) type compounds have been isolated during the course of a search for the psychoactive components present in the seed (nutmeg) and aril (mace) of the fruit of Myristica fragrans Houtt. The presence of two different structural types, analogous to the p -0 -4 ether and 2.3-dihydrobenzofuran types of dilignols, has been established. Six examples (1)-( 111) and (V)-(VIII) of the former type and two of the latter, dehydrodi-isoeugenol (IX) and 5-methoxydehydrodi-isoeugenol (X) have been isolated and their structures established. Compounds (I), (11). and (V), have been synthesised and the relative configuration of the p -0 -4 ethers has been established as erythro.

The preparation of adre~iochrorne in a pure stable crystalline form has been carried out b y the silvcr oxide osiclation of adrenaline in ~nethanol with the use of an anion-exchange resin (Dowes-l(C1-)) to remove heavy metal ions from the reaction l n i s t~~r e prior to the isolation of the product. Its paper chromatographic behavior together with that of three derivatives (adrenolutin, adrcnochrome n~onoremicarbazone, and adrenochrome monoisonicotinic acid hydrazide) in six different solvent systems has been examined. \Water was found to be the best paper chromatographic solvent so far esamined for this series of COIII~OLIII~S.Adre~lochrome (I), the substa~lce mainly responsible for the red colors produced during the mild oxidation of adrenaline (11), was hrst isolated from the products of an enzymatic oxidation by Green and Richter ( I ) . Subsequently, inorganic oxidizing agents, particularly silver oxide, were successfully employed and i t was observed that adrenochrome could be crystallized from methanol (containing a little formic acid) a t -80" (cf. Veer (2); MacCarthy (3) ; Harley-Mason (4) ; Sobotka and Austin (5)). Green and Richter reported t h a t adrenochrome was unstable both in the solid state and in solutio~l (1) ; however, Sobotka and Austin claim that the dry crystalline nlaterial can be liept indefinitely a t 0" (5).The stability of aqueous solutions of adrenochrome has been shown to bemarliedly affected by pH (cf. Zambotti and i\Joret (7)); under alkaline conditions and in the presence of certain metallic cations, particularll. zinc, adrenochrome readily rearranges into adrenolutin (N-n1ethyl-3,5,G-i11doletriol, 111) (cf. Lund (8) ; Fischer, Derouaux, Lainbot, and Lecomte (9); Harley-h11ason and Bu'Locli (10) ; Fischer and Lecomte (11)). Manz~script received Decernber

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