Ergot: Difference between revisions
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==D-lysergic acid== | ==D-lysergic acid== | ||
[[File:Lysergamide.png|right|thumb|Functional diagram of substituted ergines (see table).]] | |||
Lysergic: discovered via hydro''lys''is of ''erg''otamine. A Table I precursor under the [https://en.wikisource.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances UN Convention Against Psychotropic Substances] and a Schedule III controlled substance. About 15 tons of DLA (also seen as (+)-lysergic acid) are legitimately manufactured each year, primarily from submerged fermentation of special strains of Calviceps purpurea but also from field harvests. | Lysergic: discovered via hydro''lys''is of ''erg''otamine. A Table I precursor under the [https://en.wikisource.org/wiki/United_Nations_Convention_Against_Illicit_Traffic_in_Narcotic_Drugs_and_Psychotropic_Substances UN Convention Against Psychotropic Substances] and a Schedule III controlled substance. About 15 tons of DLA (also seen as (+)-lysergic acid) are legitimately manufactured each year, primarily from submerged fermentation of special strains of Calviceps purpurea but also from field harvests. | ||
{| class="wikitable" style="float:right" | |||
!Name !! R<sup>1</sup> !! R<sup>2</sup> !! R<sup>3</sup> | |||
|- | |||
| Ergine || H || H || H | |||
|- | |||
| Ergonovine || H || CH(CH<sub>3</sub>)CH<sub>2</sub>OH || H | |||
|- | |||
| Methergine || H || CH(CH<sub>2</sub>CH<sub>3</sub>)CH<sub>2</sub>OH || H | |||
|- | |||
| Methysergide || CH<sub>3</sub> (methyl) || CH(CH<sub>2</sub>CH<sub>3</sub>)CH<sub>2</sub>OH || H | |||
|- | |||
| LSD || H || CH<sub>2</sub>CH<sub>3</sub> (ethyl group) || CH<sub>2</sub>CH<sub>3</sub> | |||
|} | |||
'''The ergopeptides are biosynthetic derivatives of DLA, but DLA is a synthetic derivative of the ergopeptides.''' DLA was first isolated by hydrolysis of ergot alkaloids in the 1930s (Jacobs & Craig, [https://www.sciencedirect.com/science/article/pii/S0021925818757293 "The Ergot Alkaloids: II. The Degradation of Ergotinine with Alkali. Lysergic Acid"], ''Journal of Biological Chemistry'' 1934). It was first synthesized by Woodward's team in 1956 starting from 3ß-carboxyethylindole (Kornfield et al, [https://pubs.acs.org/doi/pdf/10.1021/ja01594a039 "The Total Synthesis of Lysergic Acid"], ''Journal of the American Chemical Society'' 1956-07), and numerous processes have been published since: see [https://www.mdpi.com/1420-3049/27/21/7322 this 2022 review] for full details. The manufacture of LSD requires DLA, which has been historically hydrolyzed from bulk ergot alkaloids due to the difficulty of other syntheses. Controlled biosynthesis ought cease at DLA; should you have the opportunity to acquire DLA, you're ready to go to town and/or prison. | '''The ergopeptides are biosynthetic derivatives of DLA, but DLA is a synthetic derivative of the ergopeptides.''' DLA was first isolated by hydrolysis of ergot alkaloids in the 1930s (Jacobs & Craig, [https://www.sciencedirect.com/science/article/pii/S0021925818757293 "The Ergot Alkaloids: II. The Degradation of Ergotinine with Alkali. Lysergic Acid"], ''Journal of Biological Chemistry'' 1934). It was first synthesized by Woodward's team in 1956 starting from 3ß-carboxyethylindole (Kornfield et al, [https://pubs.acs.org/doi/pdf/10.1021/ja01594a039 "The Total Synthesis of Lysergic Acid"], ''Journal of the American Chemical Society'' 1956-07), and numerous processes have been published since: see [https://www.mdpi.com/1420-3049/27/21/7322 this 2022 review] for full details. The manufacture of LSD requires DLA, which has been historically hydrolyzed from bulk ergot alkaloids due to the difficulty of other syntheses. Controlled biosynthesis ought cease at DLA; should you have the opportunity to acquire DLA, you're ready to go to town and/or prison. | ||