Lysergic acid and derivatives

Since both acids yield dihydro-derivatives there must be a readily reducible ethylenic linkage, the position of which must be conjugate with the indole nucleus to satisfy the character of the absorption spectra (Jacobs, Craig and Rothen ) and must account for the fact that lysergic acid is a weaker base than its isomeride, implying that in the former the ethylenic linkage is nearer the NMe group, which is met by placing it at C -C for lysergic acid and at C -C for wolysergic acid.  [c.529]

The Cg building block, mevalonic acid (30), has been shown again and again to lose CO2 and then serve as the pregenitor of C, C q, C2Q, and C Q systems via the isomeric pair 3,3-dimethylallyl pyrophosphate (32)-isopentenyl pyrophosphate (31) (Table 3). This explains the genesis of a variety of bases containing the pattern defined by the five-carbon branched chain common to them and to the derivatives of mevalonic acid. Included among these are that small group of alkaloids which correspond to a joining of a tryptophan (26) and a unit to produce bases such as the potent uterine stimulant agroclavine (18) and its relatives, among which are the peptide amides of lysergic acid (100, R = OH).  [c.549]

Depressant symptoms, which include burning abdominal pain, decreased excitabiUty, convulsions, nausea, and coma, become the general syndrome for all oral alkaloid poisoning. Discorine [3329-91-7] (15), a y-unsaturated lactone found in yams, is an alkaloid having the empirical formula C23H22O2N it has been isolated from Nigerian yams, thus estabUshing the discorine-type alkaloids as representative of the Dioscorea genus of plants (56). Seeds of Senecio contain alkaloids belonging to the pyrrolizidine group and, in addition to producing characteristic signs of alkaloid toxicity, these are suspected of being hepatic carcinogens. Ergotism is the disease caused by intoxication by one of at least twelve alkaloid derivatives of lysergic acid produced by a parasitic fungus (ergot) on grains. Myristicin (7), found in both nutmeg and mace, is a psychoactive agent that may be fatal in infants who consume as Httle as two whole nutmegs. Its toxicity resembles alcohol intoxication.  [c.478]

The largest single class of naturally occurring iadoles are the plant alkaloids. These occur with a wide range of stmctural diversity and are typically derived from tryptophan and terpenoid stmctural units. Several of these compounds are pharmacologically significant. Reserpiae [50-55-5] (15) acts as a tranquilizer and hypotensive agent. Although not widely used at present, it was one of the first dmgs to be iatroduced for the treatment of mental illness (38). The dimeric vinca alkaloids vincristine [57-22-7] and vinblastine [865-21-4] are used ia the treatment of Hodgkia s disease, leukemia, and other forms of cancer (39). Derivatives of the ergot alkaloid lysergic acid are used ia the treatment of migraine (40) and the diethylamide is lysergic acid diethylamide (LSD) (see Alkaloids).  [c.88]

Recently Hofmann has found that when the azide hydrochlorides of the lysergic and fsolysergic acids, or of their dihydro-derivatives, are boiled in dilute hydrochloric acid, a Curtius reaction occiys and the carboxyl is replaced by an amino-group. In this way he has prepared the following amines. They melt with decornposition and the specific rotations are for pyridine as solvent —  [c.531]

The second type, dihydro-bases (II), hydrolyses with alkali or with hydrazine to (+)-dihydro-d-wolysergic acid (II), which is probably identical with the y-dihydrolysergic acid of Jacobs and Craig. The principal characters of the dihydro-lysergic and isolysergic acids and their derivatives are summarised in the following table —  [c.533]

See pages that mention the term Lysergic acid and derivatives : [c.549]    [c.534]    [c.552]    [c.520]    [c.525]    [c.526]    [c.528]    [c.530]    [c.531]    [c.532]    [c.532]   
Thin-layer chromatography Reagents and detection methods (1990) -- [ c.98 , c.340 ]