Tropane

Tropane[1]
IUPAC name N-Methyl-8-azabicyclo[3.2.1]octane
Other names 2,3-Dihydro-8-methylnortropidine
Identifiers
CAS number	529-17-9
PubChem	637986
ChemSpider	553556 Y
ChEBI	CHEBI:35615 Y
Jmol-3D images	Image 1
SMILES N1(C)[C@H]2CC[C@@H]1CCC2
InChI InChI=1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+ Y Key: XLRPYZSEQKXZAA-OCAPTIKFSA-N Y
Properties
Molecular formula	C8H15N
Molar mass	125.211 g/mol
Density	0.9259 at 15 °C
Boiling point	163-169 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

See also

• Phenyltropane
• Tropane alkaloid

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. http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=ATROPINE. 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. http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=COCAINE. Retrieved July 25, 2005.