Isolysergic acid amide

The principle agent in this plant was found to be -lysergic acid amide, which had already been synthesized and was known as both ergine and LA-111. Other alkaloids of lesser importance found to be psychoactively influential in Turbina corymbosa were d-isolysergic acid amide (isoergine), chanodavine, elymoclavine and lysergol. 

A. Simple lysergic acid and isolysergic acid amides... 

Ergotaminine 1.18 Aci-ergotamine 0.77 Aci-ergotaminine 0.98 Lysergic acid amide 0.45 Isolysergic acid amide 0.61 Lysergic acid 0.08 Isolysergic acid 0.18... 

The usual procedures of extraction with suitable organic solvents, such as benzene, chloroform, methylene chloride and the like, or absorption with the known absorbent means, such as charcoal, bentonite and the like, under alkaline conditions, may be used for the separation and isolation of the mixture or the obtained alkaloids. The mixture, in which lysergic acid amide and isolysergic acid amide are prevalently present, can then be hydrolyzed with alkali, in known manner, to lysergic and isolysergic acid (J. Chem. Society, 1934, p. 674, and 1936, p. 1440). 

Niwaguchi, T. Inoue, T. Chromatographic Separation of Lysergic Acid Amide and Isolysergic Acid Amide in Morning Glory Seeds Journal of Chromatography (1969) 43 510-512... 

It has been shown that anion-exchange resins can sometimes be useful for the epimerisation at C(8) of isolysergic acid amides to give compounds in the more useful lysergic acid series. 

The seeds of this so-called wood rose were shown to contain lysergic and isolysergic acid amides 21). 

Genest, K. A Direct Densitometric Method on Thin-layer Plates for the Determinatin of Lysergic Acid Amide, Isolysergic Acid Amide and Clavine Alkaloids in Morning Glory Seeds ... 

Isolation of ergot alkaloids. Preparative TLC of countercurrent fractions was carried out on silica gel 60 F-254 plates (E. Merck) developed with CH2Cl2/MeOH (4 1). values were 0.42, 0.50, and 0.68 for lysergic acid amide, ergonovine, and isolysergic acid amide, respectively. Fluorescent bands on TLC plates were separately scraped from the plates, transferred to disposable Pasteur pipettes, and ergot alkaloids were then eluted with the same solvent system. Mass spectra were obtained with a Finnigan MAT 4535/TSQ instrument equipped with a DEP probe. 

Identified peaks 1, lysergic acid amide (670 /ig) plus isolysergic acid amide (520 fig) 2, N-methylloline (61 mg) 3, N-acetylloline (305 mg) 4, ergonovine (55 /ig) 5, N-formylloline (601 mg) 6, loline (31 mg) plus N-acetylnorloline (28 mg). Loline-type alkaloids determined by GC. Ergot-type alkaloids determined by HPLC with fluorescence detection and expressed as /ig ergotamine tartrate. 

Infected individuals of several grass species are more resistant to a number of insect herbivores (Clay, 1988). Further, seeds of infected species are more resistant to herbivore attack (Cheplick and Clay, 1988). Lysergic acid amide (10), isolysergic acid amide, 8-hydroxylysergic acid (15), ergonovine, chanoclavine I (7), and A(-formylloline all were isolated from Stipa robusta infected with an Acremonium endophyte (Petroski et al., 1992 Powell and Petroski, 1992). 

The basic studies on the isolation of ergolines from the seeds of Turbina corymbosa and Ipomoea tricolor, respectively, already show that ergine (lysergic acid amide) including the 8-epimeric artefact erginine (isolysergic acid amide) represents the major alkaloid of both species with about 65% of the alkaloid fraction (Hofmann and Tscherter 1960 Hofmann, 1961). 

Miller MD (1970) Isolation and identification of lysergic acid amide and isolysergic acid amide as the principal ergoline alkaloids in Argyreia nervosa, a tropical wood rose. J Ass Offic Agric Chem 53 123-127... 

Agurell, S. (1966c) Biosynthesis of ergot alkaloids in Claviceps paspali. II. Incorporation experiments with lysergic acid amide- H, isolysergic acid amide- H and ethylamine- (3. Acta Pharm. Suec., 3, 65-70. 

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