page_title: Indole alkaloid
section_title: Applications
hierarchical_section_title: Indole alkaloid / Applications
caption_attribution_description: LSD blotter with match for size comparison.
context_page_description: Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
context_section_description: Plants and fungi that contain indole alkaloids have a long history of use in traditional medicine. Rauvolfia serpentina, which contains reserpine as the active substance, was used for over 3000 years in India to treat snake bites and insanity. In medieval Europe, extracts of ergot were used in medical abortion.
  Later, the plants were joined by pure preparations of indole alkaloids. Reserpine was the second (after chlorpromazine) antipsychotic drug; however, it showed relatively weak action and strong side effects, and is not used for this purpose any longer. Instead, it is prescribed as an antihypertensive drug, often in combination with other substances.
  Other drugs that affect the cardiovascular system include ajmaline, which is a Class I antiarrhythmic agents, and ajmalicine, which is used in Europe as an antihypertensive drug. Physostigmine – an inhibitor of acetylcholinesterase – and its synthetic analogs are used in the treatment of glaucoma, Alzheimer's disease (rivastigmine) and myasthenia (neostigmine, pyridostigmine, distigmine). Ergot alkaloids ergometrine (ergobazin, ergonovine), ergotamine and their synthetic derivatives (methylergometrine) are applied against uterine bleeding, and bisindole alkaloids vinblastine and vincristine are antitumor agents.
  Animal studies have shown that ibogaine has a potential in treating heroin, cocaine, and alcohol addictions, which is associated with the ibogaine antagonism to NMDA-receptors. Medical use of ibogaine is hindered by its legal status, as it is banned in many countries as a powerful psychedelic drug with dangerous implications of overdose. However, illegal network in Europe and United States provide ibogaine for treating drug addiction.
  Since ancient times, plants containing indole alkaloids have been used as psychedelic drugs. The Aztecs used and the Mazatec people continue to use psilocybin mushrooms and the psychoactive seeds of morning glory species like Ipomoea tricolor. Amazonian tribes use the psychedelic infusion, ayahuasca, made from Psychotria viridis and Banisteriopsis caapi. Psychotria viridis contains the psychedelic drug DMT, while Banisteriopsis caapi contains  harmala alkaloids, which act as monoamine oxidase inhibitors. It is believed that the main function of the harmala alkaloids in ayahuasca is to prevent the metabolization of DMT in the digestive tract and liver, so it can cross the blood–brain barrier, whereas the direct effect of harmala alkaloids on the central nervous system is minimal. The venom of the Colorado River toad, Bufo alvarius, may have used as a psychedelic drug, its active constituents being 5-MeO-DMT and bufotenin. One of the most common recreational psychedelic drugs, LSD, is a semi-synthetic ergoline (which contains the indole moiety).
caption: LSD blotters
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