Cuscohygrine

Cuscohygrine
IUPAC name 1,3-bis- (1-methylpyrrolidin- 2-yl) -propan- 2-one
Identifiers
CAS number	454-14-8
ChemSpider	389876
KEGG	C06521
Jmol-3D images	Image 1
SMILES O=C(CC1N(C)CCC1)CC2N(C)CCC2
InChI InChI=1/C13H24N2O/c1-14-7-3-5-11(14)9-13(16)10-12-6-4-8-15(12)2/h11-12H,3-10H2,1-2H3 Key: ZEBIACKKLGVLFZ-UHFFFAOYAQ
Properties
Molecular formula	C13H24N2O
Molar mass	224.34 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cuscohygrine is a pyrrolidine alkaloid found in coca. It can be extracted from plants of the family Solanaceae as well, including Atropa belladonna (deadly nightshade), Datura inoxia and Datura stramonium (jimson weed). Cuscohygrine usually comes with other, more potent alkaloids like atropine or cocaine.

Cuscohygrine (along with the related metabolite hygrine) was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca leaves (also known as Cusco-leaves).

Cuscohygrine is an oil, which can be distilled without decomposition only in vacuum. It is easily soluble in water and forms an optically inactive crystalline hydrate C₁₃H₂₄N₂O·3H₂O, which melts at 40-41 °C.

References

• "PubChem Substance Summary". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=8752. Retrieved July 14, 2005. 
• "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=CUSCOHYGRINE. Retrieved July 14, 2005. 
• Dr. Ame Pictet (1904). The Vegetable Alkaloids. With particular reference to their chemical constitution. London: Chapman & Hall.