A. Harman
Synonyms Aribine; Loturine; Passiflorin; 2-Methyl-b-carboline; 3-Methyl-4-carboline;
Biological Sources It is obtained from the bark fruit of Passiflora incarnata L. (Passifloraceae) (May pop, Passion flower); seed of Peganum harmala L. (Rutaceae) (Harmel, Syrian Rue, African Rue), bark of Sickingia rubra (Mart.) K. Schum. (Arariba rubra Mart.), (Rubiaceae); and bark of Symplocus racemosa Roxb. (Symplocaceae).
Chemical Structure
1-Methyl-9H-pyrido [3, 4, b] indole; (C12 H10 N2).
Isolation Poindexter and Carpenter* isolated this alkaloid from the cigarette smoke.
Characteristic Features
1. It is obtained as orthorhombic crystals from heptane and cyclohexane having mp 237-238°C.
2. It has a bitter taste.
3. It exhibits distinct bright blue fluorescence in uv light.
4. It pKa’s are 7.37 and 144.6.
5. It has uvmax (methanol): 234, 287, 347 nm (log ε 4.57, 4.21, 3.66).
6. It is practically insoluble in water and freely soluble in dilute acids.
Identification Test Harman Hydrochloride (C12H10N2.HCl) It is obtained as rosettes of needles from a mixture of ethanol + 20% HCl in water which sublimes at 120-130°C.
Uses It is a narcotic hallucinogen.
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* Poindexter and Corpenter, Chem. & Ind. (London), 1962, 176.
