Tropane

Tropane^[1]

Names
IUPAC name N-Methyl-8-azabicyclo[3.2.1]octane
Other names 2,3-Dihydro-8-methylnortropidine
Identifiers
CAS Number	529-17-9
ChEBI	CHEBI:35615
ChemSpider	553556
Jmol interactive 3D	Image
PubChem	637986
InChI InChI=1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+ Key: XLRPYZSEQKXZAA-OCAPTIKFSA-N 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
SMILES 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).
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Infobox references

Tropane is a nitrogenous [3.2.1] 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. 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; there are two asymmetric carbons, but tropane is optically inactive due to symmetry.

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

See also

• Phenyltropane
• Tropane alkaloid
• Tropine

References

1. Merck Index, 11th Edition, 9689.
2. "Atropine content of plants" Check |url= value (help). USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. [Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland. Retrieved July 25, 2005.
3. "Cocaine content of plants" Check |url= value (help). USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases. [Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland. Retrieved July 25, 2005.

External links

• Tropane Chemistry