Trestolone

Trestolone was prepared as follows: Using 19-norandrost-4,6-diene-17-acetoxy-3-one, one of the conjugated steroidal enones, as a starting material, 19-norandrost-4-ene-7-methyl-17-hydroxy-3-one (Trestolone) was prepared by dissolving 62.8 g of 19-norandrost-4,6-diene-17-acetoxy-3-one and 1.0 g of CuCl in 800 g of tetrahydrofuran. The mixture was heated to 50 °C, and 8 g of trimethylaluminum was added. The mixture was stirred for 6 hours, and then 50 g of water was added to the reaction system. The mixture was stirred for 2 hours, filtered, and the filtrate was evaporated to dryness under reduced pressure. The filtrate was purified by column chromatography to obtain 42.9 g of the product Trestolone (19-norandrost-4-ene-7-methyl-17-acetoxy-3-one), with a yield of 65%.

Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in androgen replacement therapy for low testosterone levels in men but has never been marketed for medical use.

Trestolone is a synthetic androgen used as a potential hormonal male contraceptive method that induces a state of termporary infertility.

Trestolone is a potent inhibitor of the release of the luteinizing hormone (LH) and follicle stimulating hormone (FSH). As spermatogenesis requires both testosterone and FSH, it is impaired by the reduction in FSH caused by trestolone as well as the reduction in LH, and subsequent reduction in testosterone.

Side effects of trestolone include low estrogen levels and associated symptoms such as reduced sexual function and decreased bone mineral density among others.