8159. Retamine

Nomenclature

CAS number: 2122-29-4
Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-1-ol.
C15H26N2O; mol wt 250.38.
C 71.95%, H 10.47%, N 11.19%, O 6.39%.

Description and references

From bark and young branches of Genista sphaerocarpa Lam. (Retama sphaerocarpa (Lam.) Boiss.), Leguminosae. Isoln: Battandier, Malosse, Compt. Rend. 125, 360, 450 (1897); Ribas et al., An. Fis. Quim. 42, 516 (1946), C.A. 41, 4894c (1947). Structure: Bohlmann et al., Ber. 98, 659 (1965). Synthesis: Bohlmann et al., ibid. 653. Stereochemistry: Ribas et al., Tetrahedron Lett. 1965, 3181.

Chemical structure

Properties

Bitter crystals from alc, mp 165-166°. [α]D20 +46.2° (c = 1.017 in abs ethanol). Practically insol in water; slightly sol in ether; sol in chloroform, alcohol, methanol; very sol in benzene.

Derivative

Hydrochloride.

Properties

mp 272-273°.