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Isoergine, also known as isolysergic acid amide ( iso-LSA or iso-LA-819), isolysergamide, or erginine, is a serotonergic psychedelic of the ergoline and lysergamide families related to ergine (lysergic acid amide; LSA) and lysergic acid diethylamide (LSD). (1978). 9783642667770, Springer Berlin Heidelberg. ISBN 9783642667770 (1976). 9780122905599, Academic Press. ISBN 9780122905599 It is the epimer of ergine inverted at the 8 position. Along with ergine and other ergolines, isoergine occurs natural product in morning glories. It is thought to be primarily responsible for the effects of morning glory seeds.
Albert Hofmann, the discoverer of LSD's psychedelic effects, tried 2mg isoergine orally and experienced derealization, detachment from the outside world, feelings of mental emptiness, tiredness, and apathy, though no specific sensory distortions were mentioned. He described its effects as similar to those of ergine, which he had tested at doses of up to 2mg. Subsequently Heim and colleagues assessed ergine at higher doses of 3 to 6mg orally and observed toxic-like effects, while isoergine at 2 to 5mg orally produced notable hallucinogenic effects. The psychedelic effects of isoergine observed in this study included some euphoria, synaesthesia, and time dilation. However, although hallucinogenic, isoergine's effects have been described as not LSD-like. The presence of hallucinogenic effects of isoergine have also been described as quite unusual for an isolysergamide derivative.
It is thought that ergine and isoergine together may account for most or all of the effects of morning glory seeds, with ergine producing intoxication, sedation, and autonomic and isoergine producing hallucinogenic effects. Conversely, other notable constituents, including elymoclavine, lysergol, and chanoclavine, produced no psychoactive or hallucinogenic effects in humans. Ergometrine, which is a minor constituent representing up to 8% of total alkaloids, is known to produce psychedelic effects only in higher amounts (2–10mg) than those in typical doses of morning glory seeds and hence is thought to not contribute to the effects of the seeds either. Moreover, ergometrine is present in Ipomoea tricolor and Argyreia nervosa but not in Ipomoea corymbosa. Isoergine being responsible for the hallucinogenic effects of morning glory seeds is also supported by animal study. However, the poorly-stable lysergic acid hydroxyethylamides (LSHs) might still alternatively be involved in the psychedelic effects of morning glory seeds per Alexander Shulgin.
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