This report described 19 female patients (M = 23.5) diagnosed as obsessive compulsive disorder (OCD; DSM-III-R) who exhibited additional symptoms of self-mutilation, dysmenorrhea, and dysorexia. A biphasic pattern related to menstruation during the course of OCD emerged: Phase 1, amenorrheic--characterized by anorexia nervosa, amenorrhea, and aggressive behavior, and Phase 2, postamenorrheic--characterized by self-mutilation following the return of the menstrual cycle, dysorexia, and aggressive behavior. All mutilative acts were reported by the patients to be painless and consisted of slashes. Seventy percent of the patients were sexually abused during childhood. All patients underwent an open trial of clomipramine (M = 200 mg/day) for 6 months, and intensive behavior therapy for 8 weeks. Based on clinical observations and self-reports, there was a decrease in self-harm and OCD symptoms. The emergence of OCD, self-mutilation, dysorexia, and dysmenorrhea in a sequential manner may suggest a specific clinical syndrome or the presence of an OCD subset. A biological working hypothesis of a hypothalamic dysfunction with serotonergic participation was suggested.