The Contribution of cocoa additive to cigarette smoking addiction

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RIVM report 650270002 Page 108 of 207 Tryptamine 3.6 Tryptamine GENERAL IUPAC systematic name: 1H-Indole-3-ethanamine (1) Synonyms: 3-(2-aminoethyl)indole; 2-(3-indolyl)ethylamine (1) Molecular formula: C10H12N2 (1) Molecular structure H N NH 2 Molecular weight: 160.22 g/mol (1) Alifatic: yes, ethylamine group (1) Aromatic: yes, indole group (1) N containing: yes, indole and a primary amine group (1) Halogen containing: no CAS registry no.: 61-54-1 (1) Storage: R/S classification: R 11-23/24/25 and S16-27-45 (2) dangercode (transport): no data available Properties: melting point: 118 ºC (1, 3). boiling point: 136 ºC – 138 ºC (2) density: no data available refractive index: no data available solubility: soluble in ethanol, acetone. Practically insoluble in water, ether, benzene (1). substance description: color: orange (2) liquid/gas/powder: crystal needles (1, 2) odor/taste: no data available volatility: no data available pKa: 10.2 (3). PA: kcal/mol: no data available flammability: FP = 185 ºC (2) FL Limits = no data available IT = 491 ºC (2) decomposition temperature: no data available stability: no data available vapour pressure/ vapour tension (20 °C): 0.17 Pa at 25 ºC (4). vapour pressure (50 °C): no data available relative density: no data available
RIVM report 650270002 Page 109 of 207 Tryptamine octanol water partition coefficient, log P, log KOW: log P = 1.55 (4). conversion factor: no data available Critical assessment Tryptamine contains the characteristic heterocyclic indole structure, accounting for aromatic properties (electrophilic substitution). The hydrogen atom linked to the cyclic N-atom is sensitive for reaction. An additional characterising chemical feature is the presence of the aliphatic amino-group. Remarkable is the low solubilty of tryptamine both in water (polar solvent) as well as in benzene (aromatic solvent). Conclusion Tryptamine is a nitrogen-containing heterocyclic compound, linked to a short aliphatic chain with a free amino-group, resulting in an overall low polar compound that is practically insoluble in water and benzene. FUNCTION IN TOBACCO No data available AMOUNT IN TOBACCO PRODUCTS Tryptamine is a natural component of tobacco leaves. In a transgenic tobacco species, more than 1 mg of tryptamine/g fresh weight was reported, a 260-fold increase over controls (5). Therefore, we conclude that the estimated tryptamine amount in fresh tobacco leaves is ± 4 µg/g fresh weight. Tryptamine is also added to tobacco as a component of cocoa, which is used as a flavouring agent. A typical casing concentration of cocoa for cigarette tobacco is 1% (6). The average amount of tryptamine in cocoa varies from 0.69 - 0.83 µg/g (7). Assuming one cigarette weights approximately 1 g, the maximum tryptamine amount from cocoa in one cigarette is estimated to be ± 8 ng. The natural tryptamine amount in tobacco leaves is significantly higher compared with the tryptamine amount from added cocoa. AMOUNT IN SMOKE main stream: no data available side stream: no data available SOURCE (tobacco, combustion product or other) Tryptamine is an natural tobacco component and is also added to tobacco as a component of cocoa powder, which is used as flavouring agent (6). ENVIRONMENTAL LEVELS AND HUMAN EXPOSURE Tryptamine is found in plants such as: orange (0.1 µg/g) and in tomato (4 µg/g). In Egyptian dry sausage, tryptamine was found in 68% of the tested sausages. The average concentration was 12.7 mg/kg (8). After 75 days of ageing, typical Italian dry sausages made with nitrite contained tryptamine 23.9 mg/kg. Corresponding values for sausage manufactured without nitrite was 16.4 mg/kg (9). COMBUSTION PRODUCTS
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