Tropane
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| Names | |||
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| IUPAC name
8-Methyl-8-azabicyclo[3.2.1]octane
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| Other names
2,3-Dihydro-8-methylnortropidine
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| Identifiers | |||
3D model (JSmol)
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| ECHA InfoCard | 100.156.627 | ||
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |||
| C8H15N | |||
| Molar mass | 125.211 g/mol | ||
| Density | 0.9259 at 15 °C | ||
| Boiling point | 163-169 °C | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tropane is a nitrogenous bicyclic organic compound. It is mainly known for a group of alkaloids derived from it (called tropane alkaloids), which include, among others, atropine and cocaine. Both alkaloids contain tropinone from which tropane is a derivate. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane, deadly nightshade, datura, potato, tomato) .[2][3]
The nitrogen bridge is between C-1 and C-5; two asymmetric carbons, but tropane is optically inactive due to symmetry.
8-Azabicyclo[3.2.1]octane (tropane without the 8-methyl group) is known as nortropane or nor-tropane.
Condensation piperidine and pyrrolidine produce tropane.
See also
References
- ^ 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. Retrieved July 25 2005.
{{cite web}}: Check date values in:|accessdate=(help); Unknown parameter|dateformat=ignored (help) - ^ "Cocaine content of plants". USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. [Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland. Retrieved July 25 2005.
{{cite web}}: Check date values in:|accessdate=(help); Unknown parameter|dateformat=ignored (help)
External links
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