Cuscohygrine

Cuscohygrine

Names
IUPAC name 1-[(2R)-1-Methyl-2-pyrrolidinyl]-3-[(2S)-1-methyl-2-pyrrolidinyl]acetone
Identifiers
CAS Number	454-14-8
ChemSpider	21864896
Jmol interactive 3D	Image
KEGG	C06521
InChI InChI=1S/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/t11-,12+ Key: ZEBIACKKLGVLFZ-TXEJJXNPSA-N
SMILES CN1CCC[C@@H]1CC(=O)C[C@@H]2CCCN2C
Properties
Chemical formula	C13H24N2O
Molar mass	224.35 g·mol^−1
Melting point	40–41 °C (104–106 °F; 313–314 K) (trihydrate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cuscohygrine is a pyrrolidine alkaloid found in coca. It can also be extracted from plants of the family Solanaceae as well, including Atropa belladonna (deadly nightshade), Datura inoxia and Datura stramonium (jimson weed). Cuscohygrine usually occurs along with other, more potent alkaloids such as 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 that can be distilled without decomposition only in vacuum. It is soluble in water. It also forms a crystalline trihydrate which melts at 40–41 °C.

See also

• Coca alkaloids
• Dihydrocuscohygrine

References

• "USDA, ARS, National Genetic Resources Program. Phytochemical and Ethnobotanical Databases.[Online Database] National Germplasm Resources Laboratory, Beltsville, Maryland.". Retrieved July 14, 2005.
• Dr. Ame Pictet (1904). The Vegetable Alkaloids. With particular reference to their chemical constitution. London: Chapman & Hall.