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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35615 ;
ChemSpider	553556 ;
ECHA InfoCard	100.156.627
PubChem CID	637986;
UNII	62QFG0728A ;
CompTox Dashboard (EPA)	DTXSID50879243 ;
	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).

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. 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; these two are asymmetric carbons, but tropane 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.

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. 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.