653. Anhalamine

Nomenclature

CAS number: 643-60-7
1,2,3,4-Tetrahydro-6,7-dimethoxy-8-isoquinolinol; 6,7-dimethoxy-8-hydroxy-1,2,3,4-tetrahydroisoquinoline.
C11H15NO3; mol wt 209.24.
C 63.14%, H 7.23%, N 6.69%, O 22.94%.

Description and references

From Lophophora williamsii (Lemaire) Coutl. (Anhalonium lewinii Henn.), Cactaceae: Kauder, Arch. Pharm. 237, 190 (1899); Spth, Becke, Monatsh. Chem. 66, 327 (1935). Structure: eidem, Ber. 67, 2100 (1934). Synthesis: Spth, Roder, Monatsh. Chem. 43, 93 (1922); Brossi et al., Helv. Chim. Acta 47, 2089 (1964); 49, 403 (1966). Biosynthetic studies: Kapadia et al., J. Am. Chem. Soc. 92, 6943 (1970). Review: Manske in R. H. F. Manske, H. L. Holmes, The Alkaloids vol. IV (Academic Press, New York, 1954) pp 8-14.

Chemical structure

Properties

Crystals, mp 189-191°. uv max (ethanol): 274 nm (log ε 2.90). Almost insol in cold water, cold alcohol, ether. Sol in hot water, alcohol, acetone, dil acids.

Derivative

Hydrochloride dihydrate.
C11H15NO3.HCl.2H2O; mol wt 281.73.
C 46.90%, H 7.16%, N 4.97%, O 28.39%, Cl 12.58%.

Properties

Crystals from water, mp 258°.