Ergot: Difference between revisions

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, adrenaline)...

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 thus EU Category 1 precursors. So there's clearly something worth knowing about ergot!

** '''Tryptophan''': An essential amino acid (one which cannot be biosynthesized in humans), and a precursor in humans of serotonin, melatonin, and vitamin B3. Clostridium sporogenes in the human gut metabolizes tryptophan into indole.

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.

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 balls of mycotoxic jizz.

Hoffman first synthesized LSD ("Lysergsäurediethylamid", C₂₀H₂₅N₃O) 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 direct evidence of God's intervention in human affairs, but I am unconvinced.

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Diversion-o-clock! Remember those 15 tons of legitimately-produced lysergic acid? That's ''in addition to'' about ten tons of ergotamine alkaloids; i.e. your Cafergot (ergotamine tartrate + caffeine) and Syntometrine (ergometrine + oxytocin) aren't counting against that total. So there's about 25 tons of pharmaceutical precursor being generated each year. Where is it all going? Is it going anywhere where we can get it back?

My opinion is that modern LSD manufacture, barring connections to the Chinese or Indian underworlds or a few acres of toxified rye, is best accomplished via controlled biosynthesis of DLA in yeasts followed by DLA conversion in a microreactor array. Extraction and hydrolysis of alkaloids from a broth of petri-grown ergot is also completely feasible, and easily scaled to kilograms (you do not need a megagram of LSD). Either way, the chemistry is not complex, but it does require precision, patience, and a significant investment in equipment. Making effective use of precursors requires multiple rounds, as does purification of the single psychoactive stereoisomer. Performing these tedious rounds while avoiding accidental exposure is perhaps the most difficult practical aspect of manufacture.

Isolsd and lumalsd are not psychoactive, but seem to put equal stress on the body otherwise. Raising the dosage of an impure product will deliver more of these undesirable contaminants. Good product '''requires repeated conversion of stereoisomers'''.

* "Lysergamides Revisited". Nichols et al. ''Hallucinogens: An Update''. National Institute on Drug Abuse Research Monograph Series #146 1994.