Tropane

Last updated
Tropane [1]
Tropane 2.svg
Tropane-3D-sticks.png
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 InfoCard 100.156.627 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 628-350-5
PubChem CID
UNII
  • InChI=1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+ Yes check.svgY
    Key: XLRPYZSEQKXZAA-OCAPTIKFSA-N Yes check.svgY
  • 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 mass 125.211 g/mol
Density 0.9259 at 15 °C
Boiling point 163 to 169 °C (325 to 336 °F; 436 to 442 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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). [2] [3]

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.

See also

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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. Archived from the original on November 7, 2004. Retrieved July 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 from the original on November 7, 2004. Retrieved July 25, 2005.
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