ergoline

Ergoline is a chemical class of indole alkaloids that share a common ergoline nucleus. The core skeleton is a tetracyclic, nitrogen-containing indole alkaloid framework, which can bear various substituents to yield a wide range of pharmacological activities.

Naturally, ergoline alkaloids are produced by certain fungi, most notably the ergot-producing Claviceps species, such as Claviceps purpurea, which colonize flowering grasses and cereals. Ergot alkaloids accumulate in ergot sclerotia and have historically caused ergotism in humans and livestock. Endophytic fungi that live inside grasses can also synthesize ergoline alkaloids, contributing to plant defense and animal exposure.

Important ergoline derivatives include ergometrine (ergonovine) and ergotamine, which have vasoconstrictive properties and are used to prevent or treat postpartum hemorrhage and migraines, respectively. Dihydroergotamine is another migraine therapy derived from the same class. Several ergoline derivatives act as dopamine or serotonin receptor agonists, including bromocriptine, cabergoline, and pergolide, used for Parkinson's disease and prolactin-related disorders. Lysergic acid diethylamide (LSD) is a well-known semi-synthetic ergoline derivative with hallucinogenic effects.

Because of their potent vascular and central nervous system effects, ergoline alkaloids can cause serious adverse effects and were historically associated with outbreaks of ergotism. Modern medical uses rely on controlled formulations and dosing, and many ergoline compounds are regulated as pharmaceuticals or controlled substances depending on jurisdiction.

Chemically, ergoline refers to the tetracyclic nucleus derived from tryptophan and lysergic acid, with the ergoline core serving as the common scaffold for natural ergot alkaloids and their synthetic derivatives. The biosynthesis involves the ergot alkaloid pathway in fungi, producing lysergic acid and related amide derivatives.