LSH

LSH, or lysergic acid α-hydroxyethylamide, is a naturally occurring ergoline alkaloid reported in some fungi and plants associated with the Convolvulaceae family. It is structurally related to lysergic acid amide (LSA), but carries a hydroxyethyl group on the amide nitrogen. Despite recurring claims that it may contribute to the effects of morning glory seeds, its activity in humans has not been established.

Chemistry and natural occurrence

LSH is also called lysergic acid hydroxyethylamide, lysergic acid methylcarbinolamide or LAH. Its structure is similar to LSA, with a hydroxyethyl group attached to the amide nitrogen. PubChem records the compound under lysergic acid α-hydroxyethylamide and notes its occurrence in natural-product databases (PubChem compound record: LSH).

A 2024 study of ergot-alkaloid biosynthesis described an enzymatic pathway in which lysergic acid is converted to the α-hydroxyethylamide before further transformation to ergine. This documents LSH’s role in a biosynthetic sequence, without establishing how much is present in any particular plant material (Ergot alkaloid biosynthesis in Metarhizium brunneum, 2024).

Stability and chemical behaviour

The hydroxyethyl side chain has a hemiacetal-like character, which makes the compound chemically unusual. A 1967 study examined lysergic and dihydrolysergic acid α-hydroxyethylamides and described acid-catalysed changes at the asymmetric carbon in the side chain. These observations are relevant to its chemical stability and analytical identification (Studies concerning lysergic and dihydrolysergic acid α-hydroxyethylamides, 1967).

Pharmacology and proposed effects

LSH is sometimes discussed as a possible contributor to the psychoactive effects of morning glory seeds. That hypothesis has not been confirmed in controlled human research. The limited pharmacological information comes from older experiments. It does not reliably define the receptor profile or establish whether LSH itself produces a distinct psychedelic effect.

It is also unclear how much intact LSH survives in plant material and during analysis. Detection of ergine in a sample does not by itself establish whether ergine was originally present or formed through transformation of other alkaloids.

Research limitations

No controlled human study has established LSH’s subjective effects, pharmacokinetics, acute toxic range or long-term safety. The main evidence concerns natural occurrence, biosynthesis and chemical behaviour. Claims that it is responsible for the effects of particular seed preparations remain speculative.

Related lysergamides

LSH is related to LSA, LAE-32 and other lysergic acid amides. Its hydroxyethyl substituent distinguishes it from the primary amide and monoethylamide structures.