Caffeine and theobromine are members of the xanthine family. Coffee and soft drinks contain caffeine, whereas, in cacao, theobromine is the main ingredient. The mineral contents of the tooth which sucked the caffeine-containing dam’s milk were decreased. To determine if caffeine would affect enamel, dams were fed with a caffeine and pups were killed and first and second molars were extracted. Enamel was exposed to the acid solution and dissolved minerals from the enamel were measured. Calcium, phosphorus and magnesium from the first molars of the caffeine group were significantly dissolved. To determine why minerals were released, enamel was separated. The crystallite size of the enamel from the caffeine group showed decreased. If the pups with the same dietary regimen, but given a cariogenic diet, the caffeine group should show a higher incidence of dental caries. The caffeine group revealed higher caries scores. An in vitro experiment to grow apatite crystals was conducted, adding the various members of the xanthine. Theobromine produced larger crystal sizes than caffeine. Theobromine was added to the maternal diet. Dissolution experiments revealed that these minerals were far less dissolved. Comparative studies of the various parameters between theobromine and fluoride were conducted. Theobromine was superior to fluoride in every aspect.