Harmaline-Synonyms Harmidine; Harmalol Methyl Ether; O-Methyl-harmalol; 3, 4-Dihydroharmine

B. Harmaline

Synonyms Harmidine; Harmalol Methyl Ether; O-Methyl-harmalol; 3, 4-Dihydroharmine;

Biological Sources It is obtained from the seeds of Peganum harmala L. (Zugophyllaceae); and Banisteria cappi Spruce (Malpighiaceae). It is also obtained from the fruit of Passiflora incarnata L. (Passifloraceae) (Passionflower, Maypop).

Chemical Structure

4, 9-Dihydro-7-methoxy-1-methyl-3H-pyridol [3, 4,-β] indole; (C₁₃H₁₄N₂O).

Characteristic Features

1. It is obtained as orthorhombic bipyramidal prisms, or tablets from methanol; and as rhombic octahedra from ethanol having the same mp 229-231°C.

2. Its solutions give a blue fluorescence.

3. Its dissociation constant pK_a 4.2.

4. It has uv_max (methanol): 218, 260, 376 nm (log ε 4.27, 3.90 and 4.02)

5. It is found to be slightly soluble in water, ethanol, ether; and very soluble in dilute acids and hot ethanol.

Identification Tests Harmaline forms definite derivatives as shown below:

1. Harmaline Hydrochloride Dihydrate (C₁₃H₁₄N₂O.HCl.2H₂O): It is obtained as slender, yellow needles that are found to be moderately soluble in ethanol and water.

2. N-Acetylharmaline: It is obtained as needles having mp 204-205°C.

Uses

1. It is recognized as a narcotic hallucinogen.

2. It is used as a CNS-stimulant.