Cuscohygrine

Title: Cuscohygrine
CAS Registry Number: 454-14-8
CAS Name: 1,3-Bis(1-methyl-2-pyrrolidinyl)-2-propanone
Additional Names: cuskhygrine; bellaradine
Molecular Formula: C13H24N2O
Molecular Weight: 224.34
Percent Composition: C 69.60%, H 10.78%, N 12.49%, O 7.13%
Literature References: In coca leaves of various origin. Found in crude hygrine. Readily converted to hygrine by acids and bases. Isoln: Liebermann, Ber. 22, 679 (1898); Liebermann, Cybulski, ibid. 28, 578 (1895). Identity with bellaradine: Steinegger, Phokas, Pharm. Acta Helv. 30, 441 (1955). Structure: Hess, Fink, Ber. 53, 794 (1920); Sohl, Shriner, J. Am. Chem. Soc. 55, 3828 (1933); Rapoport, Jorgensen, J. Org. Chem. 14, 664 (1949). Synthesis: Späth, Tuppy, Monatsh. Chem. 79, 119 (1948); Galinovsky et al., ibid. 82, 551 (1951). Enzymatic synthesis: Tuppy, Faltaous, ibid. 91, 167 (1960). Stereochemistry: Galinovsky, Zuber, ibid. 84, 798 (1953). Biosynthesis: E. Leete, Chem. Commun. 1980, 1170.
Properties: Oily liquid, bp23 169-170°; bp14 152°; bp2 118-125°. d420 0.9733. nD20 1.4832. Miscible with water. Sol in alcohol, ether, benzene.
Boiling point: bp23 169-170°; bp14 152°; bp2 118-125°
Index of refraction: nD20 1.4832
Density: d420 0.9733
Derivative Type: Hemiheptahydrate
Properties: Needles, mp 40°.
Melting point: mp 40°
Derivative Type: Hydrobromide
Molecular Formula: C13H24N2O.2HBr
Molecular Weight: 386.17
Percent Composition: C 40.43%, H 6.79%, N 7.25%, O 4.14%, Br 41.38%
Properties: Prisms from alc, mp 234°.
Melting point: mp 234°
Cuspareine Cusparine Cy 3 Cy 5 Cyacetacide

Cuscohygrine
Chemical structure of cuscohygrine
Cuscohygrine ball-and-stick.png
Identifiers
CAS number 454-14-8
ChemSpider 389876
KEGG C06521
Jmol-3D images Image 1
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 (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 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 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.