 | |
| Names | |
|---|---|
| IUPAC name (6-Methyl-8,9-didehydroergolin-8-yl)methanol | |
| Systematic IUPAC name [(6aR,10aR)-7-Methyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methanol | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.008.136 |
| UNII | |
| |
| |
| Properties | |
| C16H18N2O | |
| Molar mass | 254.327 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Elymoclavine is anergot alkaloid (ergoline alkaloid). It can be produced fromC. fusiformis fromPennisetum typhoideum. It is a precursor in the biosynthesis ofD-(+)-lysergic acid. Ergot alkaloids are natural products derived fromL-tryptophan. They are often toxic for humans and animals. Despite that they are also well known for their pharmacological activities.[1][2]
The compound is described as being non-hallucinogenic in humans, instead producing mainlysedative effects, and as not contributing to thepsychoactive or hallucinogenic effects of morning glory seeds.[3][4][5] The doses employed were not provided.[3][5]
The main building blocks for biosynthesis of elymoclavine aretryptophan (Trp) andDMAPP. DMATrp is obtained after electrophilic substitution followed by addition (Step A below). Then an amine is methylated by an N-methyltransfersase (Step B). Next, the allyl alcohol is oxidized to the diene (Step C). After 1,4-elimination, thediene undergoes anepoxidation (Step D). Thendecarboxylation is followed by the 6-member ring formation and epoxide opened to form terminal alcohol (Step E). Obtainedchanoclavine gets oxidized to chanoclavine aldehyde (Step F). Then the second 6-member ring forms andagroclavine is obtained after additional reductase (Steps G and H). Finally elymoclavine is generated after an oxidation (Step I). The last step isNADPH-dependent, and it is suggested thatcytochrome P450 is the catalyst.[6][7]
Elymoclavine (No.6) produces mainly sedation (ISBELL and GORODETZKY,1966). [...] In the ergolene derivatives, lysergol and elymoclavine are devoid of psychotomimetic properties. [...] Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]
{{cite book}}: CS1 maint: bot: original URL status unknown (link)d-Lysergic acid amide (ergine) is the major constituent of the seeds of both Rivea corymbosa and Ipomoea violacea, together with smaller amounts of d-isolysergic acid amide (isoergine), chanoclavine, elymoclavine, and the N-(1-hydroxyethyl)amides of lysergic and isolysergic acids. [...] It is clear that the pharmacologically active constituents of ololiuqui are the isomeric lysergic acid amides. [...] Heim and his colleagues suggest that the overall effects of ololiuqui are due to these two compounds, the d-lysergic acid amide giving intoxication with strong autonomic side-effects and the d-isolysergic acid amide producing some euphoria, synaesthesia, and altered time experience. Certainly elymoclavine, lysergol, chanoclavine, and ergometrine produce no psychic changes in man (Isbell and Gorodetzky, 1966; Hofmann, 1968), though the first two do produce central excitation in animals (Yui and Takeo, 1958).
He also found that in addition to d-lysergic acid amide, d-iso-lysergic acid amide, and chanoclavine, the seeds of both plants contained elymoclavine. [...] Elymoclavine elicits excitation and central stimulation in animals (Yui 1958), but ISBELL found that elymoclavine caused chiefly sedative effects in former addicts. [...] The results also agree with the sedative effects reported after d-lysergic aeide amide (HOFMAN 1963; ISBELL; SOLMS 1956), d-iso-lysergic acid amide (HOFMANN 1963), and elymoclavine (ISBELL). [...] ISBELL, H. : Unpublished observations.
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