Epiandrosterone is a steroid hormone

Steroid hormone

A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into five groups by the receptors to which they bind: glucocorticoids, mineralocorticoids, androgens, estrogens, and progestogens...

 with weak androgenic activity. It is a natural metabolite of dehydroepiandrosterone

Dehydroepiandrosterone

5-Dehydroepiandrosterone is a 19-carbon endogenous steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans....

 via the 5-alpha reductase

5-alpha reductase

5α-reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in 3 metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism, and prostate cancer....

 enzyme. It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone

Estrone

Estrone is an estrogenic hormone secreted by the ovary as well as adipose tissue.Estrone is one of several natural estrogens, which also include estriol and estradiol...

.

Epiandrosterone has been shown to naturally occur in most mammals including pigs.

Epiandrosterone is naturally produced by the enzyme 5-alpha reductase from the adrenal hormone dehydroepiandrosterone

Dehydroepiandrosterone

5-Dehydroepiandrosterone is a 19-carbon endogenous steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans....

 (DHEA). Epiandrosterone can also be converted from the natural steroids androstanediol

Androstanediol

3β-Androstanediol is an androstanediol derived from DHT in a reaction catalyzed by the enzyme 3-β-HSD...

 via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.

Synonyms for epiandrosterone are: 3-epiandrosterone; 3β-androsterone; 3β-hydroxyetioallocholan-17-one; 5α-androstan-17-one, 3β-hydroxy-; 5β-androstan-17-one; and 3-β-hydroxyetiollocholan-17-one

See also

• Androstadienone
  Androstadienone
  Androstadienone, also known as androsta-4,16,-dien-3-one, is a chemical compound that has been described as having strong pheromone-like activities in humans. It is a metabolite of the sex hormone testosterone: however, androstadienone does not exhibit any known androgenic or anabolic effects...
  
  
• Androstatrione
• Androstenol
  Androstenol
  Androstenol is a sex pheromone in pigs, possessing a musk-like odor.It is found in large quantities in boar saliva, but also in smaller quantities in human sweat glands. It is analogous to sex hormones yet has minimal or no androgenic activity...
  
  
• Androstenone
  Androstenone
  Androstenone is a steroid found in both male and female sweat and urine. It is also found in boar's saliva, and in celery cytoplasm. Androstenone was the first mammalian pheromone to be identified. It is found in high concentrations in the saliva of male pigs, and, when sniffed by a female pig...
  
  
• Dehydroepiandrosterone
  Dehydroepiandrosterone
  5-Dehydroepiandrosterone is a 19-carbon endogenous steroid hormone. It is the major secretory steroidal product of the adrenal glands and is also produced by the gonads and the brain. DHEA is the most abundant circulating steroid in humans....
  
  
• Estratetraenol
  Estratetraenol
  Estratetraenol, also known as estra-1,3,5,16-tetraen-3-ol, is a chemical compound produced by women that has been described as having pheromone-like activities in primates, including humans...
  
  

Further reading

1. Simons RG, Grinwich DL. Immunoreactive detection of four mammalian steroids in plants. Can J Bot 67: 288-296, 1989
2. Janeczko A, Skoczowski A. Mammalian sex hormones in plants. Folia Histochem Cytobiol. 2005;43(2):71-9.Labrie F, Bélanger A, Labrie C, Candas B, Cusan L, Gomez 4. JL. Bioavailability and metabolism of oral and percutaneous dehydroepiandrosterone in postmenopausal women. J Steroid Biochem Mol Biol. 107(1-2):57-69, 2007
3. Uralets VP, Gillette PA. Over-the-counter delta5 anabolic steroids 5-androsen-3,17-dione; 5-androsten-3beta, 17beta-diol; dehydroepiandrosterone; and 19-nor-5-androsten-3,17-dione: excretion studies in men. J Anal Toxicol. 24(3):188-93, 2000