Harmaline
Structural Formula Vector Image
Title: Harmaline
CAS Registry Number: 304-21-2
CAS Name: 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
Additional Names: 1-methyl-7-methoxy-3,4-dihydro-b-carboline; 3,4-dihydroharmine; harmidine; harmalol methyl ether; O-methylharmalol
Molecular Formula: C13H14N2O
Molecular Weight: 214.26
Percent Composition: C 72.87%, H 6.59%, N 13.07%, O 7.47%
Literature References: CNS stimulant from seeds of Peganum harmala L., Zygophyllaceae: Goebel, Ann. 38, 363 (1841); from Banisteria caapi Spruce, Malpighiaceae: Hochstein, Paradies, J. Am. Chem. Soc. 79, 5735 (1957). Structure: Manske et al., J. Chem. Soc. 1927, 1. Synthesis: Späth, Lederer, Ber. 63, 120, 2102 (1930); Spenser, Can. J. Chem. 37, 1851 (1959). Identity with harmidine: Robinson, Chem. Ind. (London) 1965, 605. Pharmacology: Fuentes, Longo, Neuropharmacology 10, 15 (1971). Metabolism: Ho et al., Biochem. Pharmacol. 20, 1313 (1971). Review of structure and synthesis work: Hofmann, Sven. Farm. Tidskr. 75, 933 (1971), C.A. 76, 149609g (1972).
Properties: Orthorhombic bipyramidal prisms, tablets from methanol, rhombic octahedra from ethanol, mp 229-231°. Solns fluoresce blue. pK 4.2. uv max (methanol): 218, 260, 376 nm (log e 4.27, 3.90, 4.02). Slightly sol in water, alcohol, ether; quite sol in hot alcohol, dil acids.
Melting point: mp 229-231°
pKa: pK 4.2
Absorption maximum: uv max (methanol): 218, 260, 376 nm (log e 4.27, 3.90, 4.02)
 
Derivative Type: Hydrochloride dihydrate
Properties: Slender, yellow needles, moderately sol in water, alcohol.
 
Derivative Type: N-Acetylharmaline
Properties: Needles, mp 204-205°.
Melting point: mp 204-205°

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