Littorine

Littorine is a tropane alkaloid found in a variety of plants including Datura^[1] and Atropa belladonna.^[2] It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway.^[3][4]

Littorine

Names
Systematic IUPAC name (1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-yl (R)-2-hydroxy-3-phenylpropanoate
Identifiers
CAS Number	21956-47-8 Y
3D model (JSmol)	Interactive image
ChemSpider	391307
PubChem CID	443005
UNII	19Q4V37F3R Y
CompTox Dashboard (EPA)	DTXSID20944553
InChI InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1 Key: FNRXUEYLFZLOEZ-FXUDXRNXSA-N
SMILES CN1[C@@H]2C[C@@H](OC([C@@H](CC3=CC=CC=C3)O)=O)C[C@H]1CC2
Properties
Chemical formula	C17H23NO3
Molar mass	289.375 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

See also

• Catuabine
• Scopine

References

1. Evans, W. C.; Ghani, A.; Woolley, V. A. (1972). "Distribution of littorine and other alkaloids in the roots of Datura species". Phytochemistry. 11 (8): 2527–2529. doi:10.1016/S0031-9422(00)88530-1.
2. Nakanishi, F.; Sasaki, K.; Shimomura, K. (1998). "Isolation and identification of littorine from hairy roots of Atropa belladonna". Plant Cell Reports. 18 (3–4): 249–251. doi:10.1007/s002990050565.
3. Zabetakis, I.; Edwards, R.; Hamilton, J. T. G.; O'Hagan, D. (1998). "The biosynthetic relationship between littorine and hyoscyamine in transformed roots of Datura stramonium". Plant Cell Reports. 18 (3–4): 341–345. doi:10.1007/s002990050583.
4. Lanoue, A.; Boitel-Conti, M.; Portais, J.-C.; Laberche, J.-C.; Barbotin, J.-N.; Christen, P.; Sangwan-Norreel, B. (2002). "Kinetic Study of Littorine Rearrangement in Datura innoxia Hairy Roots by ¹³C NMR Spectroscopy". Journal of Natural Products. 65 (8): 1131–1135. doi:10.1021/np010612c. PMID 12193016.