Mibolerone
chemical compound
Mibolerone, also known as dimethylnortestosterone (DMNT) and sold under the brand names Cheque Drops and Matenon, is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was marketed by Upjohn for use as a veterinary drug. It was indicated specifically as an oral treatment for prevention of estrus (heat) in adult female dogs.
Side effects
Pharmacology
Pharmacodynamics
Mibolerone has both higher affinity and greater selectivity for the androgen receptor (AR) than does the related potent AAS metribolone (17α-methyl-19-nor-δ9,11-testosterone), although potent and significant progestogenic activity remains present. However, another study found that mibolerone and metribolone had similar affinity for the progesterone receptor (PR) but that mibolerone only had around half the affinity of metribolone for the AR.
Chemistry
Mibolerone, also known as 7α,17α-dimethyl-19-nortestosterone (DMNT) or as 7α,17α-dimethylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone). It is the 17α-methyl derivative of trestolone (7α-methyl-19-nortestosterone; MENT). Other related AAS include metribolone (17α-methyl-δ9,11-19-nortestosterone) and dimethyltrienolone (7α,17α-dimethyl-δ9,11-19-nortestosterone).
Synthesis
The original patented synthesis was revised: Precursor (also needed for Plomestane):
The reaction of Bolandione [734-32-7] (1) with triethyl orthoformate gave 3-Ethoxyestra-3,5-dien-17-one [2863-88-9] (2) in 64% yield. Organometallic reaction with methyl lithium followed by hydrolysis of the dienol ether gave Normethandrone [514-61-4] (5) in 40% yield. In an alternative synthesis, reaction of Estr-5(10)-ene-3,17-dione [3962-66-1] (3) with methanol catalyzed by malonic acid gave a near quantitivate yield of the ketal, 3,3-dimethoxyestr-5(10)-en-17-one [19257-34-2] (4). Reaction with the organometallic reagent and hydrolysis in this case afforded a much higher yield of product (86.7%) than in the first case.
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