Tropane

Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane, deadly nightshade, datura, potato, tomato). Structurally, tropane is cycloheptane with a nitrogen bridge between carbons 1 and 5 and an additional methyl group attached to the nitrogen. While carbons 1 and 5 are asymmetric carbons, tropane itself 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.

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 Y
3D model (JSmol)	Interactive image
Beilstein Reference	6379695
ChEBI	CHEBI:35615 Y
ChemSpider	553556 Y
ECHA InfoCard	100.156.627
EC Number	628-350-5
PubChem CID	637986
UNII	62QFG0728A Y
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+ 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
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). N verify (what is YN ?) Infobox references

Chemical compound

Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) and Solanaceae (including mandrake, henbane, deadly nightshade, datura, potato, tomato).^[2][3]

Structurally, tropane is cycloheptane with a nitrogen bridge between carbons 1 and 5 and an additional methyl group attached to the nitrogen. While carbons 1 and 5 are asymmetric carbons, tropane itself 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.^[4]

See also

[edit]

• Phenyltropane
• Tropane alkaloid
• Tropine

References

[edit]

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. Archived from the original on November 7, 2004. 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. Archived from the original on November 7, 2004. Retrieved July 25, 2005.
4. ^ Fan, Long; Wu, Lei; Yu, Xu-Hua; Chen, Yuan-Bin; Lin, Lin; Li, Shuo-Guo (October 2021). "The ethnopharmacology, phytochemistry, pharmacology and toxicology of the genus Erycibe (Convolvulaceae)". Journal of Ethnopharmacology. 278 114312. doi:10.1016/j.jep.2021.114312. PMID 34107330.