Isoergine
Isoergine, also known as isolysergic acid amide, isolysergamide, or erginine, is a serotonergic psychedelic of the ergoline and lysergamide families related to ergine and lysergic acid diethylamide. It is the epimer of ergine inverted at the 8 position. Along with ergine and other ergolines, isoergine occurs naturally in morning glories. It is thought to be primarily responsible for the hallucinogenic effects of morning glory seeds.
Use and effects
Isoergine occurs naturally in morning glory species, including Ipomoea tricolor, Ipomoea corymbosa, and Argyreia nervosa. It has been found to constitute 8 to 35% of total alkaloid content relative to 5 to 58% for ergine.Albert Hofmann, the discoverer of LSD's psychedelic effects, tried 2mg isoergine orally and experienced feelings of unreality, 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 altered time perception. However, although hallucinogenic, isoergine's effects have been described as not LSD-like. The presence of hallucinogenic effects of isoergine has 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 side effects 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 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 studies.
According to Alexander Shulgin in his 1997 book TiHKAL however, both ergine and isoergine are "probably correctly dismissed" as not contributing to the effects of morning glory seeds. The poorly-stable lysergic acid hydroxyethylamides might alternatively be involved in the psychedelic effects of morning glory seeds per Shulgin.