The isolation of harmane and norharmane from tobacco and cigarette smoke

Abstract Harmane and norharmane were isolated from cured tobacco and its smoke. This establishes the presence of indole alkaloids in tobacco. Quantitative studies showed that cigarette smoke contained between 15 and 20 μg of combined harmane and norharmane per gram of tobacco smoked. The tobacco itself contained only about 1 per cent of the amount found in smoke. Thus, the pyrolytic formation of the harmane alkaloids was strongly indicated. The addition of radioactive tryptophan to the tobacco resulted in the isolation of radioactive harmane alkaloids in the smoke. Further studies indicated that enough tryptophan was present in the tobacco to account for the quantities of the harmane alkaloids found in the smoke.