4616. Harmine

Nomenclature

CAS number: 442-51-3
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole; banisterine; yageine; telepathine; leucoharmine.
C13H12N2O; mol wt 212.25.
C 73.56%, H 5.70%, N 13.20%, O 7.54%.

Description and references

CNS stimulant isolated from seeds of Peganum harmala L., Zygophyllaceae: Gbel, Ann. 38, 363 (1841); Reinhard et al., Phytochemistry 7, 503 (1968); from Banisteria caapi Spruce, Malpighiaceae: Hochstein, Paradies, J. Am. Chem. Soc. 79, 5735 (1957); from Banisteriopsis inebrians Morton, Malpighiaceae: O'Connell, Lynn, J. Am. Pharm. Assoc. 42, 753 (1953). Structure: Manske et al., J. Chem. Soc. 1927, 1, 240. Synthesis: Spth, Lederer, Ber. 63B, 120 (1930); Akaboro, Saito, ibid. 2245; Hahn et al., Ber. 67B, 2031 (1934), Ann. 520, 107, 123 (1935), Ber. 71B, 2163, 2175 (1938); Harvey, Robson, J. Chem. Soc. 1938, 97. Metabolism: Slotkin, DiStefano, J. Pharmacol. Exp. Ther. 174, 456 (1970). Toxicity study: K. K. Chen et al., J. Pharmacol. Exp. Ther. 79, 127 (1943).

Chemical structure

Properties

Slender, orthorhombic prisms from methanol, mp 261° (dec). Sublimes. pKa 7.70. uv max (methanol): 241, 301, 336 nm (log ε 4.61, 4.21, 3.69). Absorption and fluorescence spectra: O. S. Wolfbeis, E. Fürlinger, Z. Phys. Chem. 129, 171 (1982). Slightly sol in water, alcohol, chloroform, ether.

Derivative

Hydrochloride dihydrate.

Properties

Crystals, mp 262° (dec), mp 321° when anhydrous. Sol in 40 parts water, freely sol in hot water. Aq solns have blue fluorescence. LD50 i.v. in mice: 38 mg/kg (Chen).