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Tropane





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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]

Tropane[1]
Names
IUPAC name

N-Methyl-8-azabicyclo[3.2.1]octane

Other names

2,3-Dihydro-8-methylnortropidine

Identifiers

CAS Number

3D model (JSmol)

Beilstein Reference

 6379695
ChEBI
ChemSpider
ECHA InfoCard 100.156.627 Edit this at Wikidata
EC Number
  • 628-350-5

PubChem CID
UNII

CompTox Dashboard (EPA)

  • 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

Chemical formula

 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).

☒N verify (what is checkY☒N ?)

Infobox references

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

edit

References

edit
  1. ^ Merck Index, 11th Edition, 9689.
  • ^ "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.
  • ^ "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.

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Tropane&oldid=1209892944"
      



    Last edited on 24 February 2024, at 01:22  





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    ●This page was last edited on 24 February 2024, at 01:22 (UTC).
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