R. A. Heacock

Identification of the major components of the essential oil of mace

Abstract Gas chromatographic and combined gas chromatographic-mass spectrometric analysis of the essential oil of mace has shown that it consists of a mixture of approximately 87.5% monoterpenes, 5.5% monoterpene alcohols, 6.5% aromatic ethers, together with 0.5% other components. Nine-monoterpene hydrocarbons, six monoterpene alcohols, two aromatic hydrocarbons, one sesquiterpene and six aromatic ethers have been identified.

Diarylpropanoids from nutmeg and mace (Myristica fragrans Houtt.).

Some diarylpropanoid (bis-C6–C3) 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 β-O-4 ether and 2,3-dihydrobenzofuran types of dilignols, has been established. Six examples (I)–(III) 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), (II), and (V), have been synthesised and the relative configuration of the β-O-4 ethers has been established as erythro.

A chromatographic comparison of the constituents of nutmeg and mace (Myristica fragrans Houtt.) with those of marihuana and hashish (Cannabis Sativa L.)

Abstract : In all the solvent systems utilized, the cannabinoids can readily be distinguished from the nutmeg and mace phenolics, which cannot be demonstrated by the preliminary field test. The cannabidiol, cannabinol and tetrahydrocannabinol have high RF values in the systems used, whilst the cannabinoids having an acid function in the molecule tend to migrate more slowly. These studies have shown that with the chromatographic systems used for the Fast Blue salt B (FBB) positive substances extractable from nutmeg and mace with cold light petroleum tend to be in the lower half of the chromatogram in the cannabinoid acid region.

The oxidation of 6-hydroxydopamine

The oxidation of 6‐hydroxydopamine (I) with molecular oxygen or potassium ferricyanide in aqueous solution has been shown to lead mainly to the formation of the uncyclized quinone 2‐(β‐aminoethyl)‐5‐hydroxy‐p‐benzoquinone (VII). However this quinone cyclized slowly, presumably to norepinochrome (i.e. indoline‐5,6‐quinone, XII), since 5,6‐dihydroxyindole (II), known to be readily formed by rearrangement of norepinochrome (XII), can be isolated from these solutions. 5,6‐Dihydroxyindolines (cf. XIII) can also be isolated (as their acetyl derivatives) from the products obtained by the addition of reducing agents to solutions containing 6‐hydroxydopamine oxidation products. No evidence was found to suggest that the possible alternative cyclization of the quinone VII to the p‐quinonoid aminochrome 6‐hydroxyindoline‐4,7‐quinone (III) occurred to any significant extent.

The Chemistry of the Aminochromes. XIX. The Reactions of Adrenochrome, Adrenolutin and 5,6-Dihydroxy-l-Methylindole with Some Silylating Agents,

Abstract Adrenolutin ( i.e. 5,6-dihydroxyl-1-methylindoxyl) and 5,6-dihydroxyl-1-methylindole reacted with the following silylating agents: hexamethyldisilazane (HMDS)—pyridine, N,O-bis(trimethylsilyl)acetamide (BSA) and trimethylsilyldiethylamine (TMSDEA) to give 3,5,6-tri(trimethylsilyloxy)-1-methylindole and 5,6-di(trimethylsilyloxy)-1-methylindole, respectively. Adrenochrome reacted with these three silylating agents to give the trimethylsilyl derivatives of adrenolutin and 5,6-dihydroxy-1-methylindole mentioned above together with other unidentified by-products.

Nuclear magnetic resonance spectroscopy of the trimethylsilyl ethers of some hydroxyphenylalkylamines

A number of hydroxyphenylalkylamines have been converted into their trimethylsilyl ethers by the action of hexamethyldisilazane in pyridine. The derivatives are completely soluble in carbon tetrachloride and these solutions are suitable for nuclear magnetic resonance spectroscopy. The nmr spectra of 16 potentially biologically active phenylalkylamines have been obtained in this way. The spectral data are presented and the significance of the results discussed.

Interaction of tetracyanoethylene with indoles on silica gel and cellulose thin-layer plates

Abstract Tetracyanoethylene and indoles readily form dark coloured π-complexes in solution. In most instances the components of such complexes formed from indoles unsubstituted in the 3-position, interact on standing with the formation of 3-tricyanovinylindole derivatives. However the use of tetracyanoethylene as a spray reagent for detecting indoles on thin-layer plates leads exclusively to the formation of these 3-tricyanovinyl substituted products. The structures of some of these compounds have been confirmed using physical and chemical methods.

The use of electron-acceptor reagents for the non-destructive detection of some phenothiazine derivatives on thin layers.

Abstract : During the past quarter of a century phenothiazines have become increasingly important in medicine due to their antihistaminic and psychotherapeutic activity. Numerous methods for the qualitative and quantitative analysis of these compounds, which have been described in the literature, have involved the use of colorimetry and many of these methods have been adapted for use in thin-layer and paper chromatography. Recent work carried out in these laboratories on the use of electron-acceptor reagents for the chromatographic detection of indoles has led to an evaluation being made of their possible use as chromogenic reagents for other compounds of pharmacological interest. The communication reports the results obtained by studying the interaction of nine different electron-acceptor reagents with thirteen common phenothiazine derivatives, several of which are widely used clinically. (Author Modified Abstract)

The thin-layer chromatography of the hydroxyindole-3-carboxylic acids.

Abstract : Two of the main problems that are often encountered in the use of paper and thin-layer chromatographic procedures for the detection and identification of hydroxyindoles are the lack of suitable standard compounds and reliable data on their R(F) values. The chromatographic behaviour of all four isomeric hydroxyindoles (hydroxylated in the benzene ring) has only been studied in a relatively few cases including indole, skatole, tryptamine, tryptophan, acetyltryptophan and oxindole. The 4-, 5-, 6- and 7-hydroxyindole-3-carboxylic acids have recently all been synthesized by unambiguous routes in these laboratories and the article reports the results of some investigations into the TLC properties of this group of hydroxyindoles. (Author)

Chromatography of some indoles on formamide-treated paper☆

Abstract The radial chromatography of a wide range of indole compounds on formamide-treated paper has been studied. The RF values and suitable methods for the detection of approximately 150 indole derivatives are reported. In general, the procedure gives excellent results with most indoles, particularly with relatively non-polar compounds.