Cuscohygrine

Cuscohygrine
Chemical structure of cuscohygrine
Names
Preferred IUPAC name
1-[(2R)-1-Methylpyrrolidin-2-yl]-3-[(2S)-1-methylpyrrolidin-2-yl]propan-2-one
Identifiers
3D model (JSmol)
3DMet
ChemSpider
KEGG
UNII
  • 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
  • CN1CCC[C@@H]1CC(=O)C[C@@H]2CCCN2C
Properties
C13H24N2O
Molar mass 224.348 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).

Cuscohygrine is a bis N-methyl pyrrolidine alkaloid found in coca plants. It can also be extracted from plants of the family Solanaceae, including Atropa belladonna (deadly nightshade) and various Datura species. 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.