Lysergic acid hydroxyethylamide
-Lysergic acid α-hydroxyethylamide (LSH, LAH), also known as -lysergic acid methyl carbinolamide, is a is a Lysergamide and alkaloid of the Ergoline family, it is present in higher concentrations in the parasitic fungi species "Claviceps", mainly the Claviceps Paspali, also in Claviceps Purpurea. This fungi grows in various species in the Convolvulaceae family like the Ipomoea violacea (Heavenly Blue Morning Glory), the Rivea corymbosa (Ololiuhqui), and the Argyreia nervosa (Hawaiian Baby Woodrose). Heavenly Blue Morning Glory and Hawaiian Baby Woodrose especially contain high amounts of LSH, with content varying between species and by how fresh the seeds are. LSH is a psychoactive Ergoline and has effects similar to LSD due to similarity in the structure and is the main psychoactive compound found in Claviceps Paspali and in (fresh) Heavenly Blue Morning Glory Seeds. LSH is unstable and breaks down into LSA quickly, so old seeds often only contains LSA and iso-LSA. When the seeds are fresh, they contain significantly higher amounts of LSH. Chemistry 

The structure is similar to LSD, with the N,N- diethylamide group replaced by an N- (1- hydroxyethyl)amide in -lysergic acid α-hydroxyethylamide. Pharmacology 
LSH has an affinity for several dopamine and serotonin recetors Mainly the 5-HT2a Receptor like most psychedelics in the human brain. LSD is a partial agonist on many dopamine and serotonin receptors, so it is highly likely that LSH is also an agonist at dopamine and serotonin receptors. Effects 

One of the  alkaloids in the seeds of Rivea corymbosa (Ololiuhqui), Argyreia nervosa (Hawaiian Baby Woodrose), and Ipomoea violacea (Tlitliltzin)  are ergine (LSA) and isoergine (its epimer).-lysergic acid α-hydroxyethylamide is very limited/undocumented in human studies. LSH side effects include sedation, nausea, stimulation, hallucinations (similar to LSD), and euphoria. The headspace is described by many as feeling drunk. Legality 

-lysergic acid α-hydroxyethylamide is unscheduled and uncontrolled in the United States, but possession and sales of it for human consumption could potentially be prosecuted under the Federal Analog Act because of its structural similarities to LSD. Although doubtful as breaks down into LSA which is a Schedule 3 drug and therefore not applicable to the Federal Analog Act

See also 

 Ergoline
 Lysergic acid
 LSA
 LSD
 Ergot
 Hawaiian baby woodrose (Argyreia nervosa)
 Ololiuhqui (Rivea corymbosa)
 Tlitliltzin (Ipomoea violacea)

References

External links 
 Ergot - A Rich Source of Pharmacologically Active Substances by Albert Hofmann

Lysergamides
Secondary alcohols
Ergot alkaloids