Substituted β-carboline

A substituted β-carboline, also known as a substituted 9H-pyrido[3,4-b]indole, is a chemical compound featuring a β-carboline moiety with one or more substitutions. β-Carbolines include more than one hundred alkaloids and synthetic compounds. The effects of these substances depend on their respective substituent. Natural β-carbolines primarily influence brain functions but can also exhibit antioxidant[1] effects. Synthetically designed β-carboline derivatives have recently been shown to have neuroprotective,[2] cognitive enhancing and anti-cancer properties.[3]

β-Carbolines are indole alkaloids featuring a fused pyridine and indole ring structure similar to tryptamine, forming a three-ringed system with variable saturation in the third ring. β-Carboline alkaloids naturally occur widely in prokaryotes, plants, animals, certain marine tunicates, and foods like coffee and smoked meats, and are also responsible for the fluorescence of scorpion cuticles under ultraviolet light. β-Carbolines occurring naturally in Peganum harmala (Syrian rue) are known as harmala alkaloids.[4]

Some β-carbolines, like harmaline, are hallucinogenic.[5][6][7] According to Alexander Shulgin, harmaline is the only β-carboline that has been extensively studied and well-established as a hallucinogen.[5][6][7] β-Carbolines are known to act as monoamine oxidase inhibitors (MAOIs), among possessing other activities.[4][8] They are an essential component of ayahuasca, by inhibiting the metabolism of the psychedelic dimethyltryptamine (DMT).[8][4]

  1. ^ Francik R, Kazek G, Cegła M, Stepniewski M (March 2011). "Antioxidant activity of beta-carboline derivatives". Acta Poloniae Pharmaceutica. 68 (2): 185–189. PMID 21485291.
  2. ^ Gulyaeva N, Aniol V (June 2012). "Good guys from a shady family". Journal of Neurochemistry. 121 (6): 841–842. doi:10.1111/j.1471-4159.2012.07708.x. PMID 22372749. S2CID 205624339.
  3. ^ Aaghaz S, Sharma K, Jain R, Kamal A (April 2021). "β-Carbolines as potential anticancer agents". European Journal of Medicinal Chemistry. 216 113321. doi:10.1016/j.ejmech.2021.113321. PMID 33684825. S2CID 232159513.
  4. ^ a b c Egger K, Aicher HD, Cumming P, Scheidegger M (September 2024). "Neurobiological research on N,N-dimethyltryptamine (DMT) and its potentiation by monoamine oxidase (MAO) inhibition: from ayahuasca to synthetic combinations of DMT and MAO inhibitors". Cell Mol Life Sci. 81 (1) 395. doi:10.1007/s00018-024-05353-6. PMC 11387584. PMID 39254764.
  5. ^ a b Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
  6. ^ a b Shulgin AT (1977). "Profiles of Psychedelic Drugs: 4. Harmaline". Journal of Psychedelic Drugs. 9 (1): 79–80. doi:10.1080/02791072.1977.10472029. ISSN 0022-393X. Retrieved 11 April 2025. Close biosynthetic relatives of harmaline (harmine and tetrahydroharmine) are known components of plants of several other genera which have medical use but no reputation as hallucinogens [...] The effective dose range of harmaline in man is 70-100 mg i.v., or 300-400 mg orally. The initial effects are noted about one hour following oral administration and persist for about 6 hours [...] The indicators of physical toxicity are common and often severe. Paresthesias of hands, feet, or face are almost always present with the onset of effects, and are usually followed by the sensation of numbness. There can be isolated symptoms such as pressure in the head or chest, nausea and distressful vomiting, dizziness, and general malaise. Mydriasis and pressor effects are never seen. The anxiety and general discomfort encourages a withdrawal from social contact, and a quiet dark environment is preferred by most subjects. The modality most consistently affected by harmaline is the visual sense. There can be vivid images generated, often in the form of meaningful dream-like sequences, and frequently containing subject matter such as wild animals or jungle scenes. Other reported visual syntheses are limited to the generation of geometric patterns which are entertaining but not felt to be of any intrinsic significance.
  7. ^ a b Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023. An additional family of compounds should be mentioned here, the β-carbolines. [...] In nature, they usually are found in one of three degrees of hydrogenation: harmine, harmaline, and tetrahydroharmine. [...] Only harmaline, one of the principal components of Ayahuasca, has a reputation for being intrinsically an active hallucinogen. The aromatic analog, harmine, has little if any psychotropic activity.
  8. ^ a b Cao R, Peng W, Wang Z, Xu A (2007). "beta-Carboline alkaloids: biochemical and pharmacological functions". Curr Med Chem. 14 (4): 479–500. doi:10.2174/092986707779940998. PMID 17305548.
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