Uterotropic 6-methoxybenzoxazolinone is an adrenergic agonist and a melatonin analog

6-Methoxybenzoxazolinone (MBOA) is a compound isolated from grasses which has gonadotropic effects in a variety of animals. The weak beta-adrenergic agonist character of MBOA is shown by its in vitro stimulation of adenylate cyclase from several tissues. Tritiated MBOA bound specifically to particulate fractions from uterus is also displaced by alpha- and beta-adrenergic compounds. The adrenergic properties of MBOA suggest it may exert diverse effects including direct actions on gonadotropin synthesis and release. The mixed adrenergic agonist ephedrine and the antidepressant imipramine were also found to be uterotropic in the vole Microtus montanus following injection protocols used with MBOA. MBOA is structurally similar to melatonin (5-methoxy-N-acetyltryptamine); [3H]melatonin which binds to uterine and pineal membranes is displaced by MBOA and by other adrenergic agents. The fact that MBOA is a beta-adrenergic agonist and a melatonin analog can account for stimulatory and inhibitory effects of this compound on sexual development.