Gigantine

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title: "Gigantine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["methyl-compounds", "norsalsolinol-ethers", "phenols", "tetrahydroisoquinoline-alkaloids"] topic_path: "general/methyl-compounds" source: "https://en.wikipedia.org/wiki/Gigantine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| ImageFile = Gigantine v2.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageAlt = | IUPACName = 6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinolin-5-ol | OtherNames = 1,2-Dimethyl-5-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline | Section1 = {{Chembox Identifiers | CASNo1 = 32829-58-6 | ChemSpiderID = 533407 | KEGG1 = C09445 | PubChem = 613653 | UNII1 = 5QO2DDT36D | StdInChI=1S/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3 | StdInChIKey = HRJQUAXWKYISJC-UHFFFAOYSA-N | InChI1=1S/C13H19NO3/c1-8-10-7-11(16-3)13(17-4)12(15)9(10)5-6-14(8)2/h7-8,15H,5-6H2,1-4H3/t8-/m0/s1 | InChIKey1 = HRJQUAXWKYISJC-QMMMGPOBSA-N | SMILES = CC1C2=CC(=C(C(=C2CCN1C)O)OC)OC | SMILES1 = C[C@H]1C=2C(=C(O)C(OC)=C(OC)C2)CCN1C | Section2 = {{Chembox Properties | C=13 | H=19 | N=1 | O=3 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Gigantine is a tetrahydroisoquinoline alkaloid found in Carnegiea gigantea and other related cactus species. It was first discovered along with macromerine in 1967. Gigantine is found in significant quantities in many mescaline-containing cactus species, but it is unclear whether it contributes to their psychoactive effects. The compound has been suspected to be hallucinogenic based on animal studies in cats and monkeys, but has not been evaluated in humans.

References

References

  1. (2002). "The Simple Plant Isoquinolines". [[Transform Press]].
  2. Bruhn JG, Lundström J. (1976). "Alkaloids of Carnegiea gigantea. Arizonine, a new tetrahydroisoquinoline alkaloid". Lloydia.
  3. [[Keeper Trout & friends]]. (2013). "Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1)". Mydriatic Productions/Better Days Publishing.
  4. (April 1967). "Two new alkaloids in cacti". Tetrahedron Lett.

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methyl-compoundsnorsalsolinol-ethersphenolstetrahydroisoquinoline-alkaloids