Tropane

Tropane^[1]

Names

N-Methyl-8-azabicyclo[3.2.1]octane

Other names

2,3-Dihydro-8-methylnortropidine

Identifiers

3D model (Jmol)

ECHA InfoCard

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
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

Properties

C₈H₁₅N

125.211 g/mol

0.9259 at 15 °C

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).

verify (what is ^YN ?)

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.

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.
↑ "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.

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