Ergine
[16][17][18][19][20] Lysergic acid hydroxyethylamide is very vulnerable to this hydrolysis,[21][22] and many analyses of ergoline-containing fungi show little to no LAH and substantial amounts of ergine.[23][24] Methylergonovine and methylmethylergonovine (methysergide) have also been found in a natural product in only one study;[25] these are documented as semisynthetic chemicals, so the findings need to be repeated for certainty.Albert Hofmann stated that ergine induces a "psychotomimetic" effect with "a marked narcotic component": "Tired, dreamy, incapable of clear thoughts."a feeling of sinking into nothing" Heim 1968 also noted "paraesthesia", "synesthesia" and an "overestimation of the time that had passed" (isoergine), but also concluded, "our experiments with ᴅ-lysergic acid amide also confirm the results that Sᴏʟᴍꜱ had made with this substance, namely a predominantly sedative intoxication."Hofmann emphasized this sedative effect: "Furthermore there is not only a quantitative difference between the principles of Ipomoea [tricolor] and Turbina corymbosa and LSD; there is likewise a qualitative one, LSD being a very specific hallucinogen, whereas the psychic effects of lysergic acid amide and the total alkaloids of these two plants are characterized by a pronounced narcotic component (Hofmann, 1968)."[64] Ergine interacts with serotonin, dopamine, and adrenergic receptors similarly to but with lower affinity than lysergic acid diethylamide (LSD).A three strep mechanism is proposed to form 4-L-DMAT: the formation of an allylic carbocation, a nucleophilic attack of the indole nucleus to the cation, followed by deprotonation to restore aromaticity and to generate 4-L-DMAT.[69] 4-Dimethylallyltyptophan N-methyltransferase (EasF) catalyzes the N-methylation of 4-L-DMAT at the amino of the tryptophan backbone, using S-Adenosyl methionine (SAM) as the methyl source, to form 4-dimethylallyl-L-abrine (4-DMA-L-abrine).[69] The conversion of 4-DMA-L-abrine to chanoclavine-I is thought to occur through a decarboxylation and two oxidation steps, catalyzed by the FAD dependent oxidoreductase, EasE, and the catalase, EasC.The biosynthesis of ergine in Claviceps purpurea will be exemplified, in which agroclavine is produced following the formation of chanoclavine-l-aldehyde, catalyzed by EasA through a keto-enol tautomerization to facilitate rotation about the C-C bond, followed by tautomerization back to the aldehyde and condensation with the proximal secondary amine to form an iminium species, which is subsequently reduced to the tertiary amine and yielding argoclavine.[74] Similarly, ingestion of morning glory seeds by Mazatec tribes to "commune with their gods" was reported by Richard Schultes in 1941 and is still practiced today.[87] Many people desire purified seed extracts, but the efficacy of this is questionable, as even pure ergine and ergonovine have shown toxic effects.However, possession of the pure compound without a prescription or a DEA license would be prosecuted, as ergine, under the name "lysergic acid amide", is listed under Schedule III of the Controlled Substances Act.[99] In New Zealand, ergine is a controlled drug, however the plants and seeds of the morning glory species are legal to possess, cultivate, buy, and distribute.
PregnancycategoryRoutes ofadministrationintramuscular injectionATC codeLegal statusPharmacokineticMetabolismExcretionIUPAC nameCAS NumberChemSpiderChEMBLCompTox DashboardECHA InfoCardFormulaMolar massMelting pointSMILESergolinealkaloidConvolvulaceaeIpomoea tricolorIpomoea corymbosaArgyreia nervosalysergic acid propanolamidelysergic acid hydroxyethylamide (LAH)lysergic acid hydroxymethylethylamide (ergonovine)methysergideergoamidesClaviceps purpureaPeriglandulasleepy grassAlbert Hofmann5-HT1Aserotonindopamineadrenergic receptorsaffinitylysergic acid diethylamide5-HT2A receptorsprenylationdimethylallyl diphosphatemevalonic acidcarbocationindoleN-methyltransferaseS-Adenosyl methioninechanoclavine-IFAD dependent oxidoreductasecatalaseshort-chain dehydrogenase/reductaseagroclavinetautomerizationCytochrome P450 monooxygenaseselymoclavineisomerizationD-lysergic acidnonribosomal peptide synthasemorning gloryMazatecRichard SchultesR. Gordon WassonZapotecOaxacaRivea corymbosaCentral Intelligence AgencyMKULTRASedationhallucinationsEuphoriaNauseaVasoconstrictionDelusionAnxietyParanoiaIrregular heartbeatdeathspharmacologicalself-harmimpaired judgementdrug interactionssuicideingestionfalling offbuildingHawaiian baby woodrosealcoholA. nervosaControlled Substances ActControlled Drugs and Substances ActList of entheogenic/hallucinogenic speciesList of psychoactive plantsTlitliltzinAnvisaDiário Oficial da UniãoBibcodePowell WThe Anarchist CookbookJ. Chem. Soc.ErowidErgolinesLysergic acid2-Bromo-LSD (BOL-148)AmesergideBromerguride (2-bromolisuride)BromocriptineCabergolineDihydroergocornineDihydroergocristineDihydroergocryptineDihydroergotamineEpicriptineErgocornineErgocristineErgocryptineErgoloidErgometrineErgometrinineErgostineErgotamineErgotoxineErgovalineLisurideLY-215,840Lysergic acid methyl esterLysergine