Lysergic acid amides

The compounds 12,14 and 15 can be prepared from parent lysergic acid amides by bromination with NBS or PHT, but not the compounds of the type 12. The latter structure is very sensitive and under these circumstances only degradation products were obtained. Besides it was necessary to use much milder reagent, e.g. bromine bonded onto polymeric matrix with polyvinylpyrrolidone or polyvinylpyridine structure (29) ... 

Scheme 13. Metabolism of lysergic acid amide congeners by Streptomyces roseochromogenes. 

Extraction of Lysergic Acid Amides from Woodrose Seeds or Powdered Ergot... 

The lysergic acid to lysergic acid amide reaction has been designed to utilize minimal quantities of solvents in order to squeeze as much material as possible into ordinary laboratory glassware. 

The mother liquors and the two washes containing methanol are collected and combined. A one normal solution of potassium hydroxide in methanol is added in approximately equal volume to the combined washes and mother liquors. The solution is then filtered and the filter washed with a few ml of methanol. The filtrates are allowed to stand at room temperature for two to three hours to reequilibrate the iso-lysergic acid amides from the mother liquors. About 500 ml of water is then added and the mixture extracted with 2.5 liters of methylene chloride in divided portions in a separatory funnel. The combined extracts are shaken with 25 grams of anhydrous magnesium sulfate and filtered. The filtrate is taken to dryness on the rotary vacuum evaporator, care taken not to heat above 55° C. The material is purified in the same manner as that from the original reaction mixture using approximately one fourth the quantities of solvents and alumina as for the original. 

Ololiuqui Turbina corymbosa Flowering Lysergic acid amide... 

Plant derived indoleamines, resembling 5-HT, include 5-methoxydimethyl tryptamine [bufotenine], psilocin, psilocybine, lysergic acid amides and dime-thyltryptamine (DMT), one of the most powerful hallucinogens. DMT and bufotenine occur for in example seeds from the Anadenanthera tree, used as a snuff called Yopo by South American Indians. 

There is no evidence that lysergic acid amide (ergine) is formed by simple amidation in ergot. From young cultures of Claviceps purpurea a partly purified enzyme could be isolated (90) which is capable of... 

It would also be conceivable to regard d-lysergic acid amide as an intermediate for peptide alkaloids. Groger et al. (98) however showed this hypothesis to be improbable. In the same paper attention is drawn to another interesting fact. Some experiments were performed in which [14C,15N valine was introduced into C. purpurea strain Pepty 695, a fungus known to produce ergokryptine and ergocornine as the major alkaloids. 

K. W. Crawford, The identification of lysergic acid amide in baby hawaiian woodrose by mass spectrometry, J. Forens. Sci., 75 588 (1970). 

Active constituents D-lysergic acid amide and ergometrine. 

Active Constituents D-lysergic acid amide, lysergol, and turbicoryn (a crystalline glucoside). 

Effects LSD-like experience lasting about 6 hours, with relaxed feelings afterwards. Nausea may be experience during first hour. D-lysergic acid amide is a hallucinogen. Turbicoryn stimulates the CNS and has anti-tension properties. 

Contraindications Persons with a history of liver disorders should not take lysergic acid amides. 

Botanical Sources of Lysergic Acid Amides, 89-99 Rye and Other Grasses, 89 Morning Glories, 95 Hawaiian Woodroses, 98... 

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