The Contribution of cocoa additive to cigarette smoking addiction

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Page 176 of 207 RIVM report 650270002 Anandamide 3.10 Anandamide GENERAL IUPAC systematic name: no data available Synonyms: Arachidonoyl ethanolamide; N-Arachidonoyl-2-hydroxyethylamide; Arachidonylethanolamide; 5,8,11,14-Eicosatetraenoylethanolamide; N-(2- Hydroxyethyl)anachidonamide; N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide (all-Z)- (1) Molecular formula: C22H37NO2 (2) Molecular structure O CH 2 N H OH Molecular weight: 347.5 g/mol (2) Alifatic: yes Aromatic: no N containing: yes Halogen containing: no CAS registry no.: 94421-68-8 (2) Storage: R/S classification: S 24/25 (2) dangercode (transport): no data available Properties: melting point: no data available boiling point: no data available density: 0.92 g/ml (2) refractive index: no data available solubility: soluble in ethanol (2) substance description: color: light yellow (2) liquid/gas/powder: liquid, oil (2) odor/taste: no data available volatility: no data available pKa: no data available PA: no data available flammability: FP = no data available FL Limits = no data available IT = no data available decomposition temperature: no data available stability: no data available vapour pressure/ vapour tension (20 °C): no data available vapour pressure (50 °C): no data available relative density: no data available
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.
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