Tropane

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title: "Tropane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["tropanes"] topic_path: "general/tropanes" source: "https://en.wikipedia.org/wiki/Tropane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470617919 | Reference = | ImageFileL1 = Tropane 2.svg | ImageFileR1 = Tropane-3D-sticks.png | IUPACName = N-Methyl-8-azabicyclo[3.2.1]octane | OtherNames = 2,3-Dihydro-8-methylnortropidine |Section1={{Chembox Identifiers | Abbreviations = | Beilstein = 6379695 | ChemSpiderID_Ref = | ChemSpiderID = 553556 | EINECS = 628-350-5 | InChI = 1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+ | InChIKey = XLRPYZSEQKXZAA-OCAPTIKFBA | StdInChI_Ref = | StdInChI = 1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+ | StdInChIKey_Ref = | StdInChIKey = XLRPYZSEQKXZAA-OCAPTIKFSA-N | InChIKey1 = XLRPYZSEQKXZAA-OCAPTIKFSA-N | CASNo_Ref = | CASNo = 529-17-9 | UNII_Ref = | UNII = 62QFG0728A | PubChem = 637986 | SMILES = N1(C)[C@H]2CC[C@@H]1CCC2 | RTECS = | MeSHName = | ChEBI_Ref = | ChEBI = 35615 | KEGG_Ref = | KEGG = |Section2={{Chembox Properties | Formula = C8H15N | MolarMass = 125.211 g/mol | Appearance = | Density = 0.9259 at 15 °C | MeltingPt = | MeltingPt_notes = | BoilingPtC = 163 to 169 | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = }} |Section7={{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | HPhrases = | PPhrases = | GHS_ref = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = |Section6={{Chembox Pharmacology | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental =

Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane, deadly nightshade, datura, potato, tomato).

Structurally, tropane is cycloheptane with a nitrogen bridge between carbons 1 and 5 and an additional methyl group attached to the nitrogen. While carbons 1 and 5 are asymmetric carbons, tropane itself is optically inactive due to mirror symmetry.

8-Azabicyclo[3.2.1]octane (tropane without the N-methyl group) is known as nortropane or nor-tropane.

References

References

  1. ''Merck Index'', 11th Edition, '''9689'''.
  2. "Atropine content of plants". USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. [Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland.
  3. "Cocaine content of plants". USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. [Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland.
  4. (October 2021). "The ethnopharmacology, phytochemistry, pharmacology and toxicology of the genus Erycibe (Convolvulaceae)". Journal of Ethnopharmacology.

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tropanes