Konstitution und Synthese des Salsolins

Späth, Ernst; Orechoff, A.; Kuffner, Friedrich

doi:10.1002/cber.19340670718

Cited by 22 publications

(9 citation statements)

References 6 publications

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“…Vanillin benzyl ether (60g) (Spith, Orechoff & Kuffner, 1934), nitroethane (25g), piperidine (1.9ml) and butylamine (1.25ml) in benzene (125ml) were refluxed for 40h, a Dean-Stark trap being used to remove the water formed. The mixture was washed with M-HCI (2 x 200ml) and then water (3 x 200ml).…”

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confidence: 99%

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The metabolic fate of amphetamine in man and other species

Dring

Smith

Williams

1970

Biochemical Journal

247

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1. The fate of [(14)C]amphetamine in man, rhesus monkey, greyhound, rat, rabbit, mouse and guinea pig has been studied. 2. In three men receiving orally 5mg each (about 0.07mg/kg), about 90% of the (14)C was excreted in the urine in 3-4 days. About 60-65% of the (14)C was excreted in 1 day, 30% as unchanged drug, 21% as total benzoic acid and 3% as 4-hydroxyamphetamine. 3. In two rhesus monkeys (dose 0.66mg/kg), the metabolites excreted in 24h were similar to those in man except that there was little 4-hydroxyamphetamine. 4. In greyhounds receiving 5mg/kg intraperitoneally the metabolites were similar in amount to those in man. 5. Rabbits receiving 10mg/kg orally differed from all other species. They excreted little unchanged amphetamine (4% of dose) and 4-hydroxyamphetamine (6%). They excreted in 24h mainly benzoic acid (total 25%), an acid-labile precursor of 1-phenylpropan-2-one (benzyl methyl ketone) (22%) and conjugated 1-phenylpropan-2-ol (benzylmethylcarbinol) (7%). 6. Rats receiving 10mg/kg orally also differed from other species. The main metabolite (60% of dose) was conjugated 4-hydroxyamphetamine. Minor metabolites were amphetamine (13%), N-acetylamphetamine (2%), norephedrine (0.3%) and 4-hydroxynorephedrine (0.3%). 7. The guinea pig receiving 5mg/kg excreted only benzoic acid and its conjugates (62%) and amphetamine (22%). 8. The mouse receiving 10mg/kg excreted amphetamine (33%), 4-hydroxyamphetamine (14%) and benzoic acid and its conjugates (31%). 9. Experiments on the precursor of 1-phenylpropan-2-one occurring in rabbit urine suggest that it might be the enol sulphate of the ketone. A very small amount of the ketone (1-3%) was also found in human and greyhound urine after acid hydrolysis.

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“…( +)-2-Amino-1-(4'-hydroxyphenyl)propan-1-ol. To a solution of p-benzyloxypropiophenone (48g; Spath et al 1934) in methylene dichloride (250ml), solid CaCO3 (25g) was added. The mixture was heated under reflux with stirring and bromine (10.25 ml) was added dropwise over 1.5 h to keep the mixture a pale yellow.…”

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The metabolic fate of amphetamine in man and other species

Dring

Smith

Williams

1970

Biochemical Journal

247

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“…(+)-(R)salsolinol hydrobromide, (−)-(S)-salsolinol hydrobromide, and rac-isosalsoline hydrochloride were synthesized in our laboratory using established synthetic routes. 31,32 The optical rotation of the salsolinols was determined with a manual Perkin-Elmer Model 141 polarimeter (Perkin-Elmer Bodenseewerk GmbH, Ü berlingen, Germany). All other reagents were from Merck (Darmstadt, Germany).…”

Section: Materials and Methods Chemicalsmentioning

confidence: 99%

O-methylation of (+)-(R)- and (?)-(S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetra-hydroisoquinoline (salsolinol) in the presence of pig brain catechol-o-methyltransferase

Hötzl

Thomas

1997

Chirality

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“…Veratraldehyde was prepared in 90% yield according to the method of Barger and Silberschmidt (5); it melted at 43-44°. o-Benzylvanillin was obtained in 95% yield by a modification of the process reported by Spáth, Orekhov, and KuEner (6) for the preparation of o-benzylisovanillin. 5-Chlorovanillin was obtained by the methods of Menke and Bentley (7).…”

Section: Wavelength A0mentioning

confidence: 99%

“…The inhibiting concentration against Aspergillus niger and Penicillium glaucum was greater than 0.21% in all cases. 6 From dilute ethanol. = The product was obtained as a colorless oil boiling at 185°/3.5 mm., " 1.5911.…”

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REACTIONS OF VANILLIN AND ITS DERIVED COMPOUNDS. XI.¹ CINNAMIC ACIDS DERIVED FROM VANILLIN AND ITS RELATED COMPOUNDS^{2, 3}

Pearl¹,

Beyer²

1951

J. Org. Chem.

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In continuing our studies on the toxicities and ultraviolet absorption characteristics of esters of vanillic and related acids, it was desired to investigate the substituted cinnamic acids related to vanillin. These cinnamic acids are easilyprepared by condensation of the desired aldehyde with malonic acid in the presence of a trace of piperidine with pyridine as a solvent, in accordance with the Doebner modification of the Perkin reaction. The actual procedure employed in this study is an adaptation of the above reaction made by Vorsatz (1) for the preparation of cinnamic acids having a free phenolic group, and is recommended by Johnson (2) for the preparation of ferulic acid. The Vorsatz adaptation employs long standing at room temperature instead of the short boiling originally used by Doebner (3). We have found this modification to be equally satisfactory for the preparation of nonphenolic cinnamic acids. In this study cinnamic acids were prepared from the following aldehydes: vanillin, veratraldehyde, 5-nitrovaniIlin, 5-chlorovanilIin, o-benzylvanillin, piperonal, and orthovanillin. Only in the case of the 5-nitrovanillin was heating necessary to obtain reaction. The reaction of orthovanillin with malonic acid in the Vorsatz procedure yielded a crystalline compound melting at 119-120°, the structure of which was not ascertained, but which yielded orthoferulic acid when boiled with alkali or when allowed to stand for an extended period. No trace of a coumarin or coumarincarboxylic acid was obtained.These acids were esterified with anhydrous ethanol in the presence of sulfuric acid to give good yields of the ethyl esters. Data for the acid and the ester preparations are found in Table I (references to earlier preparations are included). The inhibiting concentrations of the esters were determined for the four representative aerobic microorganisms-namely, non-sporeforming-(Aerobacter aerogenes) and sporeforming-(Bacillus mycoides) bacteria and molds (Aspergillus

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Konstitution und Synthese des Salsolins

Cited by 22 publications

References 6 publications

The metabolic fate of amphetamine in man and other species

The metabolic fate of amphetamine in man and other species

O-methylation of (+)-(R)- and (?)-(S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetra-hydroisoquinoline (salsolinol) in the presence of pig brain catechol-o-methyltransferase

REACTIONS OF VANILLIN AND ITS DERIVED COMPOUNDS. XI.¹ CINNAMIC ACIDS DERIVED FROM VANILLIN AND ITS RELATED COMPOUNDS^{2, 3}

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Konstitution und Synthese des Salsolins

Cited by 22 publications

References 6 publications

The metabolic fate of amphetamine in man and other species

The metabolic fate of amphetamine in man and other species

O-methylation of (+)-(R)- and (?)-(S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetra-hydroisoquinoline (salsolinol) in the presence of pig brain catechol-o-methyltransferase

REACTIONS OF VANILLIN AND ITS DERIVED COMPOUNDS. XI.1 CINNAMIC ACIDS DERIVED FROM VANILLIN AND ITS RELATED COMPOUNDS2, 3

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REACTIONS OF VANILLIN AND ITS DERIVED COMPOUNDS. XI.¹ CINNAMIC ACIDS DERIVED FROM VANILLIN AND ITS RELATED COMPOUNDS^{2, 3}