Disclosed herein are compounds which are metabolites of trans-clomiphene which have a purity of greater than 95% when measured by HPLC. Also disclosed are pharmaceutical compositions comprising these metabolites and their use in treating disorders including secondary hypogonadism, type 2 diabetes, elevated cholesterol, elevated triglycerides, wasting, lipodystrophy, female and male infertility, benign prostate hypertrophy, prostate cancer, breast cancer, ovarian cancer and endometrial cancer.