Objectives: To describe microscopic figures of tooth after exposure to clove cigarette, pure eugenol and ordinary cigarette. To describe microstructure of specific caries and compared with usual caries and to analyze the smoke of clove cigarette and ordinary cigarette. Method: The laboratory study was design to evaluate tooth before and after exposure to clove cigarette, ordinary cigarette and pure eugenol with different doses (1,2,3 packs of cigarette) as well as different duration of exposure (20, 30 and 40 days). Quantitative analysis was conducted using Electron Dispersion X-Ray Microanalysis (EDX) to measure the inorganic matrix of enamel and dentin. The surface changes were examined by Scanning Electron Microscope. Smoke analysis by smoking machine of both ordinary and clove cigarettes was conducted to observe the differences in its content. Results: Microscopic figures showed that narrowing of inter prismatic space and some of the hydroxy apatite crystals were overlapped each other, however quality of binding with organic matter of tooth was unclear. Inorganic rate analysis of specimens by EDX indicated that after prolonged exposure to clove cigarettes or pure eugenol, the calcium rate increased and oxygen rate decreased. Phosphates however remained relatively stable as same as specific caries caused by habitual clove cigarette smoking. On the other hand some of hydroxy apatite crystal in usual caries were missing. Cigarette smoke analysis indicated that clove cigarette smoke, beside containing nicotine and tar found in ordinary cigarettes, also contained eugenol. Conclusion: The process of tooth decay, caused by clove cigarette and eugenol,would seem it was denaturizing of protein from organic substance of teeth. Further studies on the mechanism of binding inorganic and organic matter of the decay process using nano technology may be undertaken. The study was funded by NIHRD, Indonesia.