Ergot: Difference between revisions
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[[File:Ergoline.png|right|thumb|The ergoline skeleton looks not entirely unlike a cock-n-balls.]] | [[File:Ergoline.png|right|thumb|The ergoline skeleton looks not entirely unlike a cock-n-balls.]] | ||
Ergot is pronounced ur-git, '''not''' er-go. Highly toxic, it ought not be consumed. Properly modified, it has many uses, primarily due to fortuitous similarity between the ergoline skeleton and the monoamide neurotransmitters (e.g. serotonin, dopamine, | Ergot is pronounced ur-git, '''not''' er-go. Highly toxic, it ought not be consumed. Properly modified, it has many uses, primarily due to fortuitous similarity between the ergoline skeleton and the monoamide neurotransmitters (e.g. serotonin, dopamine, noradrenaline)... | ||
Ergot alkaloids ergonovine and ergotamine (and their salts) are both original List I controlled precursors under the [https://en.wikipedia.org/wiki/Controlled_Substances_Act 1970 Controlled Substances Act]. Ergocristine was added to List I in 2010 (see the DEA's 2010-03 ''[https://www.erowid.org/library/periodicals/microgram/microgram_2010-03.pdf Microgram Journal]''). Derivatives lysergic acid and its amide ("ergine") are Schedule III controlled substances under the CSA, and ergine is a Class A precursor in the United Kingdom. Subsequent derivative lysergic acid diethylamide is an original Schedule I controlled substance, and its functional analogues (any chemical "substantially similar", as if that had any kind of precise meaning) are treated as Schedule I due to the [https://en.wikipedia.org/wiki/Federal_Analogue_Act 1986 Federal Analogue Act]. Ergotamine, lysergic acid, and ergometrine (ergonovine) are all on Table I of the INCB Red List, and are thus EU Category 1 precursors. So there's clearly something worth knowing about ergot! | Ergot alkaloids ergonovine and ergotamine (and their salts) are both original List I controlled precursors under the [https://en.wikipedia.org/wiki/Controlled_Substances_Act 1970 Controlled Substances Act]. Ergocristine was added to List I in 2010 (see the DEA's 2010-03 ''[https://www.erowid.org/library/periodicals/microgram/microgram_2010-03.pdf Microgram Journal]''). Derivatives lysergic acid and its amide ("ergine") are Schedule III controlled substances under the CSA, and ergine is a Class A precursor in the United Kingdom. Subsequent derivative lysergic acid diethylamide is an original Schedule I controlled substance, and its functional analogues (any chemical "substantially similar", as if that had any kind of precise meaning) are treated as Schedule I due to the [https://en.wikipedia.org/wiki/Federal_Analogue_Act 1986 Federal Analogue Act]. Ergotamine, lysergic acid, and ergometrine (ergonovine) are all on Table I of the INCB Red List, and are thus EU Category 1 precursors. So there's clearly something worth knowing about ergot! | ||
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===Paspalic acid=== | ===Paspalic acid=== | ||
Paspalic acid is an isomer of lysergic acid, and will spontaneously convert. Jean-Claude Gaullier's 2000 [https://patents.google.com/patent/US6242603B1/en patent] specifies a high-yield (81.6% RRi, 2.8% iso-LA) isomerization using a tetra(C1-C6)alkylammonium hydroxide. In that same patent, he cites previous isomerizations using 2N sodium hydroxide or 0.5N potassium hydroxide, reporting 59.3% RRi with NaOH (6.8% iso-LA) and 49.8% RRi with KOH (1% iso-LA), described in the Swiss journal Helvetica Chimica Acta in 1981 and 1964, respectively. [https://patents.google.com/patent/WO2005082902A1/en Cvac + Mojczek claimed] to do even better purity-wise in 2005 by following the metallic hydroxide with a methanol wash. | Paspalic acid is an isomer of lysergic acid, and will spontaneously convert. Jean-Claude Gaullier's 2000 [https://patents.google.com/patent/US6242603B1/en patent] specifies a high-yield (81.6% RRi, 2.8% iso-LA) isomerization using a tetra(C1-C6)alkylammonium hydroxide. In that same patent, he cites previous isomerizations using 2N sodium hydroxide or 0.5N potassium hydroxide, reporting 59.3% RRi with NaOH (6.8% iso-LA) and 49.8% RRi with KOH (1% iso-LA), described in the Swiss journal <i>Helvetica Chimica Acta</i> in 1981 and 1964, respectively. [https://patents.google.com/patent/WO2005082902A1/en Cvac + Mojczek claimed] to do even better purity-wise in 2005 by following the metallic hydroxide with a methanol wash. | ||
===Extraction of ergopeptines from ergot broth=== | ===Extraction of ergopeptines from ergot broth=== | ||
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Lysergic: discovered via hydro''lys''is of ''erg''otamine (-ic: a suffix meaning "characterized by"). | Lysergic: discovered via hydro''lys''is of ''erg''otamine (-ic: a suffix meaning "characterized by"). | ||
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 wherever eastern europeans can be convinced to tromp around filling their baskets with | 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 wherever eastern europeans can be convinced to tromp around filling their baskets with mycotoxic jizz. | ||
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(6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide is a guaranteed cure for boredom. | (6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide is a guaranteed cure for boredom. | ||
Hoffman first synthesized LSD ("Lysergsäurediethylamid", C<sub>20</sub>H<sub>25</sub>N<sub>3</sub>O) 1938-11-16 at Sandoz Pharmaceuticals. It was the twenty-fifth substance synthesized in a program of systematically exploring the ergot alkaloids, hence the name LSD-25. On 1943-04-19, he accidentally ingested about 250 micrograms, and discovered its potent effects. Some claim this to be | Hoffman first synthesized LSD ("Lysergsäurediethylamid", C<sub>20</sub>H<sub>25</sub>N<sub>3</sub>O) 1938-11-16 at Sandoz Pharmaceuticals. It was the twenty-fifth substance synthesized in a program of systematically exploring the ergot alkaloids, hence the name LSD-25. On 1943-04-19, he accidentally ingested about 250 micrograms, and discovered its potent effects. Some claim this to be evidence of God's direct intervention in human affairs, but I am unconvinced. | ||
===Production from DLA=== | ===Production from DLA=== | ||