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Tropane

From Wikipedia, the free encyclopedia
Tropane[1]
Names
IUPAC name
N-Methyl-8-azabicyclo[3.2.1]octane
Other names
2,3-Dihydro-8-methylnortropidine
Identifiers
3D model (JSmol)
6379695
ChEBI
ChemSpider
ECHA InfoCard100.156.627Edit this at Wikidata
EC Number
  • 628-350-5
UNII
  • InChI=1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+ checkY
    Key: XLRPYZSEQKXZAA-OCAPTIKFSA-N checkY
  • InChI=1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+
    Key: XLRPYZSEQKXZAA-OCAPTIKFBA
  • Key: XLRPYZSEQKXZAA-OCAPTIKFSA-N
  • N1(C)[C@H]2CC[C@@H]1CCC2
Properties
C8H15N
Molar mass125.211 g/mol
Density0.9259 at 15 °C
Boiling point163 to 169 °C (325 to 336 °F; 436 to 442 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Tropane is anitrogenousbicyclicorganic compound. It is mainly known for the otheralkaloids derived from it, which includeatropine andcocaine, among others.Tropane alkaloids occur inplants of the familiesErythroxylaceae (includingcoca) andSolanaceae (includingmandrake,henbane,deadly nightshade,datura,potato,tomato).[2][3]

Structurally, tropane iscycloheptane with a nitrogen bridge between carbons 1 and 5 and an additionalmethyl group attached to the nitrogen. While carbons 1 and 5 areasymmetric carbons, tropane itself is optically inactive due to mirror symmetry.

8-Azabicyclo[3.2.1]octane (tropane without theN-methyl group) is known asnortropane ornor-tropane.[4]

See also

[edit]

References

[edit]
  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. Archived fromthe original on November 7, 2004. RetrievedJuly 25, 2005.
  3. ^"Cocaine content of plants".USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. [Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland. Archived fromthe original on November 7, 2004. RetrievedJuly 25, 2005.
  4. ^Fan, Long; Wu, Lei; Yu, Xu-Hua; Chen, Yuan-Bin; Lin, Lin; Li, Shuo-Guo (October 2021). "The ethnopharmacology, phytochemistry, pharmacology and toxicology of the genus Erycibe (Convolvulaceae)".Journal of Ethnopharmacology.278 114312.doi:10.1016/j.jep.2021.114312.PMID 34107330.
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