Lysergic acid hydroxyethylamide
Lysergic acid hydroxyethylamide, also known as lysergic acid N-amide or as lysergic acid methyl carbinolamide, is a lysergamide alkaloid related to the psychedelic drug lysergic acid diethylamide. It is found in ergot species such as Claviceps paspali and Claviceps purpurea and in the seeds of morning glory species which contain the Symbiotic fungi species Periglandula ipomoeae.
Use and effects
According to Albert Hofmann, Alexander Shulgin, and other researchers, LSH might be a psychedelic drug and might contribute to or be substantially responsible for the hallucinogenic effects of morning glory seeds. Relatedly, per Shulgin in his 1997 book TiHKAL, both ergine and isoergine are "probably correctly dismissed" as not contributing to the effects of morning glory seeds. However, LSH has not been studied in humans and this hypothesis has not been tested or confirmed. LSH is said to be extremely chemically unstable, and rapidly degrades into ergine, which has made its investigation difficult.Pharmacology
Pharmacodynamics
The pharmacology of LSH has been very limitedly studied. It has about 30 to 50% of the potency as ergometrine as an oxytocic in the isolated guinea pig and rabbit uterus, produces sympathomimetic effects very similar to those of ergine in mice and rabbits, and has weak ergotamine-like sympatholytic or antiadrenergic effects. These effects are potentially indicative of LSH having LSD-like activity. However, LSH is not known to have been tested in humans. LSH may simply function as a prodrug of ergine.Chemistry
The structure of LSH is similar to that of LSD, with the N,''N-diethylamide group replaced by an N''-amide in -lysergic acid α-hydroxyethylamide. LSH is also very similar in structure to ergonovine, which is also known as lysergic acid hydroxyisopropylamide.Natural occurrence
C. paspali and C. purpurea are ergot-spreading fungi. Periglandula, Clavicipitacepus fungi, are permanently symbiotically connected to an estimated 450species of Convolvulaceae and thus generate LAH in some of them. The most well-known ones are Ipomoea tricolor, Turbina corymbosa, and Argyreia nervosa. LAH is structurally similar to ergonovine, which is also known as lysergic acid hydroxymethylethylamide.The more well-known analogue, ergine, is more prominent in analytical results because LAH easily decomposes to ergine. Ergine is only present because of the decomposition of LAH ; it is not generated. Indeed, a 2016 analysis found that fresher I. tricolor seeds contained more LAH than the other two batches analyzed