654. Anhalonidine

Nomenclature

CAS number: 17627-77-9
(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-methyl-8-isoquinolinol; 6,7-dimethoxy-8-hydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline.
C12H17NO3; mol wt 223.27.
C 64.55%, H 7.67%, N 6.27%, O 21.50%.

Description and references

From mescal buttons, the buds of Lophophora williamsii (Lemaire) Coult. (Anhalonium lewinii Henn.) Cactaceae: Heffter, Ber. 27, 2975 (1894); 29, 221 (1896); Kauder, Arch. Pharm. 237, 190 (1899). Structure and synthesis from 3-acetoxy-4,5-dimethoxy-N-acetylphenethylamine: Spth, Passl, Ber. 65, 1778 (1932); from mescaline: Brossi et al., Helv. Chim. Acta 47, 2089 (1964). Biosynthesis: Kapadia et al., J. Am. Chem. Soc. 92, 6943 (1970).

Chemical structure

Properties

Small octahedra from benzene, mp 160-161°. uv max (ethanol): 270 nm (log ε 2.81). Strong base. Freely sol in water, alcohol, chlorofom, hot benzene. Sparingly sol in ether. Insol in petr ether. Solns of anhalonidine acquire a reddish color on standing.