Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a

steroid hormone A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into two classes: corticosteroids (typically made in the adrenal cortex, hence ''cortico-'') and sex steroids (typically made in the gonads or placenta). Withi ...

with weak androgenic activity. It is a

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...

testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...

and

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues includi ...

(DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and

Kurt Tscherning Kurt is a male given name of Germanic or Turkish origin. ''Kurt'' or ''Curt'' originated as short forms of the Germanic Conrad, depending on geographical usage, with meanings including counselor or advisor. In Turkish, Kurt means "Wolf" and is ...

. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline

androsterone Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of tes ...

(most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to

estrone Estrone (E1), also spelled oestrone, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estriol. Estrone, as well as the other estrogens, are synthesized ...

. Epiandrosterone has been shown to naturally occur in most mammals including pigs. Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone

DHEA Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functi ...

. Epiandrosterone can also be produced from the natural steroids

androstanediol Androstanediol may refer to: * 3α-Androstanediol (5α-androstane-3α,17β-diol) – an endogenous neurosteroid, weak androgen and estrogen, and intermediate to androsterone * 3β-Androstanediol (5α-androstane-3β,17β-diol) – an endogenous es ...

via

17β-hydroxysteroid dehydrogenase A hydroxysteroid is a molecule derived from a steroid with a hydrogen replaced with a hydroxy group. When the hydroxy group is specifically at the C3 position, hydroxysteroids are referred to as sterols, with an example being cholesterol. See ...

or from

androstanedione Androstanedione, also known as 5α-androstanedione or as 5α-androstane-3,17-dione, is a naturally occurring androstane (5α-androstane) steroid and an endogenous metabolite of androgens like testosterone, dihydrotestosterone (DHT), dehydroepian ...

via 3β-hydroxysteroid dehydrogenase.

See also

References

Further reading