Resonance enhanced multiphoton ionization technique, used in time of flight mass spectrometry, has displayed the ability to distinguish structurally similar chemical species, including conformers of the same species. This is beneficial for identifying and characterizing molecular species that are typically difficult to analyze with other techniques. Although qualitative analysis has been demonstrated using this technique, quantitative data has been challenging to collect without internal standards. Quantitative analysis may be possible by using an internal standard, and by implementing a more controlled technique of sample preparation. We have been presented with historical artifacts, pieces of ancient vessels, hypothesized to have been used to store beverages such as coffee, tea, chocolate or wine. The ability to determine relative ratios of the chemical compounds caffeine, theophylline, and theobromine, which are xanthine derivatives, will most likely provide strong evidence to confirm, or eliminate, the hypothesized use of these vessels. Additionally, the use of internal standards could prove to be beneficial in similar analytical experiments. We attempted to synthesize deuterated caffeine, theophylline, and theobromine in order to use as an internal standards with their non-deuterated forms. Samples of each xanthine derivative along with their internal standards were coated on a sample holder using a vapor deposition chamber. The prepared samples were analyzed using a Resonance enhanced multiphoton ionization-Time of flight-Mass spectrometer (REMPI-TOF-MS). We expected to obtain data that permits adequate use of these internal standards to help in future experiments. The data we have obtained has contributed to our progress.