The Contribution of cocoa additive to cigarette smoking addiction

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