Background:Adolescents often experiment with drug use, which can impact on their health and well-being and increase the probability of problem drug use. Yet, not enough is known about which psychological indicators is related with the initiation of drug use among young adults and have predictive power.Materials and Methods:Participants in this study were 311 boys (school and college students) aged 15–17. Data were collected in the towns of Moscow region. A modified version of Dembo-Rubinstein test was used to assess the self-evaluation (SE). A questionnaire and detection of drugs in urine were used to identify drug users. Binary logistic regression analysis based on SE with the inclusion of interactive effects between predictors was used for prediction of drug use.Results:Drug users, compared to nondrug users, are characterized by lower actual SE of health, happiness, success in learning, mind and desired SE of appearance, and higher desired SE of relationships with friends. The developed nonlinear regression model for prediction of boys’ involvement in drug use among young boys in the towns of Moscow region has a sensitivity of 82.7% at a specificity of 79.0%.Conclusions:Dembo-Rubinstein test of SE is a sensitive measure to identify boys at risk of involvement in drug use. Application of the regression model based on SE may contribute to the useful solution in preventing any onset of early drug use.