The Contribution of cocoa additive to cigarette smoking addiction

RIVM report 650270002 Page 177 of 207
Anandamide
octanol water partition coefficient, log P, log KOW: no data available
conversion factor: not relevant
Critical assessment
The compound is a bioactive amide of a fatty acid, which was isolated and then its
structure determined by NMR and several MS-techniques and confirmed by
synthesis. Values for classical physical properties could not be found in literature.
Mass spectrometric behavior reveals that anandamide easily undergoes thermal
dehydration upon energy supply (3).
Striking structural features are: the aliphatic hydroxylgroup, the amide bond and the
multi-unsaturated carbon chain.
Conclusion
‘Pure’anandamide looks like an oil, will lose water upon heating and possesses some
active chemical sites such as an hydroxyl group, an amide group and four unsaturated
carbon-carbon bonds.
FUNCTION IN TOBACCO
No data available.
AMOUNT IN TOBACCO PRODUCTS
A source of anandamide in cigarettes is cocoa powder. A typical casing concentration
of cocoa powder for cigarette tobacco is 1% (4).
The amount of anandamide found in cocoa powder is around 0.05 µg/g (5).
Assuming one cigarette weights approximately 1 g, the anandamide amount from
cocoa powder in one cigarette is estimated to be ± 0.5 ng.
AMOUNT IN SMOKE
main stream: no data available.
side stream: no data available.
SOURCE
Anandamide is added to tobacco as a component of cocoa powder, which is used as
flavouring agent (4).
ENVIRONMENTAL LEVELS AND HUMAN EXPOSURE
Anandamide was found in small quantities in human milk (± 3 µg/l) as an
endogenous products (6).
The environmental exposure to anandamide is unknown.
COMBUSTION PRODUCTS
No data available.
CONSENSUS REPORTS
No data available.
STANDARDS AND RECOMMENDATIONS
ADI: No data available.
TWANL = MAC: No data available.