Table 1.
Identification and Quantitation (Peak Areas) of the 0–12 h Urinary Metabolites of Arecoline and Arecaidine in the Mousea
| mass [M + H]+ | retention time (min) | deduced formula [M] | error (ppm) | identity (corresponding compound in Figure 2) | arecoline (p.o.) mean ± SD | arecoline (i.p.) mean ± SD | arecaidine (p.o.) mean ± SD | arecaidine (i.p.) mean ± SD |
|---|---|---|---|---|---|---|---|---|
| 142.087 | 0.28-0.30 | C7H11NO2 | 0 | arecaidine (II) | 36.1 ± 4.5 | 33.7 ± 17.8 | 64.8 ± 28.8 | 124.7 ± 35.3 |
| 144.102 | 0.30-0.31 | C7H13NO2 | 2.1 | N-methylnipecotic acid (V) | 384.0 ± 84.5 | 335.2 ± 142.9 | 446.3 ± 50.9 | 527.7 ± 54.7 |
| 156.104 | 0.63 | C8H13NO2 | 7.0 | arecoline (I) | 6.5 ± 3.8 | 20.3 ± 9.5 | 0 | 0 |
| 158.027 | 1.55 | n.d. | n.d. | UK-1 | 56.7 ±2.1 | 55.2 ± 10.7 | 61. 3 ±28.7 | 55.6 ± 35.4 |
| 158.083 | 0.33-0.35 | C7H11NO3 | 5.1 | arecaidine N-oxide (IV)* | 2.4 ± 1.4 | 12.7 ± 4.4 | 16.6 ±3.1 | 19.8 ±11.0 |
| 160.105 | 0.35 | n.d. | n.d. | UK-2 | 0 | 0 | 11.0 ±3.8 | 6.1 ± 3.4 |
| 166.088 | 1.58 | n.d. | n.d. | UK-3 | 0 | 76.9 ± 74.0 | 58.7 ± 43.2 | 76.1 ± 74.9 |
| 172.097 | 1.16 | C8H13NO3 | 5.2 | arecoline N-oxide (III)* | 428.6 ± 30.2 | 339.5 ± 53.6 | 0 | 0 |
| 199.108 | 0.31-0.32 | C9H14N2O3 | 1.0 | arecaidinylglycine (VII) | 9.7 ± 1.2 | 20.1 ±7.0 | 25.2 ± 6.8 | 49.6 ± 26.2 |
| 201.123 | 0.35 | C9H16N2O3 | 1.0 | N-methylnipecotylglycine (VI) | 32.2 ±4.1 | 69.9 ±27.1 | 70.4 ±12.1 | 187.9 ± 96.5 |
| 216.124 | 2.60 | C10H17NO4 | 4.2 | arecaidinylglycerol (VIII) | 15.2 ±7.1 | 30.3 ± 32.3 | 22.8 ± 0.4 | 15.8 ± 2.2 |
| 249.114 | 2.37 | n.d | n.d. | UK-4 | 2.9 ± 1.0 | 3.3 ± 1.3 | 2.8 ±3.1 | 2.9 ±1.8 |
| 263.125 | 2.35-2.44 | n.d. | n.d. | UK-5 | 14.0 ± 3.5 | 13.7 ± 6.6 | 22.4 ±11. 2 | 11.6 ±3.5 |
| 279.121 | 1.48 | n.d. | n.d. | UK-6 | 5.4 ± 5.2 | 7.4 ± 4.6 | 0 | 0 |
| 305.115 | 0.46-0.48 | C12H20N2O5S | 1.0 | arecaidine mercapturic acid (IX) | 14.8 ± 5.0 | 30.3 ± 25.6 | 45.1 ± 34.8 | 39.9 ± 9.2 |
| 319.133 | 1.22-1.23 | C13H22N2O5S | 2.5 | arecoline mercapturic acid (X) | 7.1 ±0.2 | 14.0 ± 6.1 | 0 | 0 |
| 335.128 | 1.99 | C13H22N2O6S | 2.1 | arecoline N-oxide mercapturic acid (XI)* | 7.9 ± 2.9 | 4.4 ± 2.1 | 0 | 0 |
| 343.187 | 1.17 | C20H26N2O4 | 4.6 | arecoline N-oxide (dimer) (III) | 15.0 ± 2.4 | 35.0 ± 20.6 | 0 | 0 |
| 343.296 | 5.77 | n.d. | n.d. | UK-7 | 0 | 0 | 9.4 ± 16.4 | 0 |
| 344.207 | 3.80 | n.d. | n.d. | UK-8 | 6.4 ± 2.8 | 14.5 ± 6.6 | 12.5 ± 8.6 | 14.4 ± 12.1 |
| 482.173 | 2.00 | n.d. | n.d. | UK-9 | 1.6 ±2.0 | 0 | 7.5 ± 7.9 | 37.6 ± 34.5 |
| total area | 1046 | 1116 | 876.8 | 1170 |
a
n.d., not determined; 0 area, peak not detected;
*
, peak disappears on reduction with TiCl3.