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Androsterone (ADT) is a steroid hormone
Steroid hormone

Steroid hormones are steroids that act as hormones. Steroid hormones can be grouped into five groups by the receptor s to which they bind: glucocorticoids, mineralocorticoids, androgens, estrogens, and progestagens....
 with weak androgenic activity. It is made in the liver
Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
 from the metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
 of testosterone
Testosterone

Testosterone is a steroid hormone from the androgen group. In mammals, testosterone is primarily secreted in the testis of males and the ovaries of females, although small amounts are also secreted by the adrenal glands....
. 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, 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.Estrone is one of the three estrogens, which also include estriol and estradiol....
.

Celery
Celery

Apium graveolens is a plant species in the family Apiaceae commonly known as celery or celeriac depending on whether the petioles or roots are eaten....
 is claimed to contain androsterone however this is a mistake.






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Androsterone (ADT) is a steroid hormone
Steroid hormone

Steroid hormones are steroids that act as hormones. Steroid hormones can be grouped into five groups by the receptor s to which they bind: glucocorticoids, mineralocorticoids, androgens, estrogens, and progestagens....
 with weak androgenic activity. It is made in the liver
Liver

The liver is a vital organ present in vertebrates and some other animals; it has a wide range of functions, a few of which are detoxification, protein synthesis, and production of biochemicals necessary for digestion....
 from the metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
 of testosterone
Testosterone

Testosterone is a steroid hormone from the androgen group. In mammals, testosterone is primarily secreted in the testis of males and the ovaries of females, although small amounts are also secreted by the adrenal glands....
. 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, 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.Estrone is one of the three estrogens, which also include estriol and estradiol....
.

Celery
Celery

Apium graveolens is a plant species in the family Apiaceae commonly known as celery or celeriac depending on whether the petioles or roots are eaten....
 is claimed to contain androsterone however this is a mistake. Celery actually contains 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....
, which has a different structure to Androsterone and is otherwise unrelated. Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromone
Pheromone

A pheromone is a chemical that triggers a natural behavioral response in another member of the opposite gender of the same species. There are alarm signal pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology....
. Androsterone has been shown to naturally occur in pine
Pine

Pines are Pinophyta trees in the genus Pinus, in the family Pinaceae. They make up the monotypic subfamily Pinoideae. There are about 115 species of pine, although different authorities accept between 105 and 125 species....
 pollen
Pollen

Pollen is a fine to coarse powder consisting of Gametophyte , which produce the male gametes of spermatophyta. A hard coat covering the pollen grain protects the sperm cells during the process of their movement between the stamens of the flower to the pistil of the next flower....
 and is well known in many animal
Animal

Animals are a major group of multicellular, eukaryotic organisms of the Kingdom Animalia or Metazoa. Their body plan eventually becomes fixed as they develop, although some undergo a process of metamorphosis later on in their life....
 species
Species

In biology, a species is one of the basic units of biological classification and a taxonomic rank. A species is often defined as a group of organisms capable of interbreeding and producing fertile offspring....
. (2)

Androsterone and its 3b isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 (epiandrosterone) are naturally produced by the enzyme 5aReductase from the adrenal hormone DHEA (dehydroepiandrosterone). Androsterone can also be converted from the natural steroids 5aAndrostanediol via 17b-Hydroxysteroid dehydrogenase or from 5aAndrostanedione via 3a-Hydroxysteroid dehydrogenase.

Androsterone provides the basic skeleton describing an androgen with a 3 a/b hydroxyl group and a 17 position ketone. Descriptive modifiers can be added like "epi" to signify a 3b hydroxyl and "#-ene" to signify the double bond placement. This basic structure can be modified in mammals by dehydrogenating it via many enzymes to create DHEA compounds that include 1-ene, 4-ene, 5-ene isomers. These isomers have been shown to be naturally occurring in mammals along with several unique structures including 4-Hydroxy-4-Dehydroepiandrosterone and 6-Keto-4-Dehydroepiandrosterone. Synthetically the combinations of dehydrogenated variants are vast and can include many unique structures.

EpiAndrosterone (CAS# 481-29-8) is a direct 3b isomer and has almost all of the characteristics of Androsterone.

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....
  • Androstatrione
  • Androstenol
    Androstenol

    Androstenol is a sex pheromone, possessing a musk-like odor. It is found in large quantities in boar saliva, but also in smaller quantities in human sweat glands....
  • 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....
  • Dehydroepiandrosterone
    Dehydroepiandrosterone

    Dehydroepiandrosterone is a multi-functional steroid that has been implicated in a broad range of biological effects in humans and other mammals....
  • 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 both primates and humans....


External links

1. Experientia. 1979 Dec 15;35(12):1674-5.Links The boar-pheromone steroid identified in vegetables. Claus R, Hoppen HO.

2. FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland

3. Rao MS, Ide H, Alvares K, Subbarao V, Reddy JK, Hechter O, Yeldandi AV. Comparative effects of dehydroepiandrosterone and related steroids on peroxisome proliferation in rat liver. Life Sci. 52(21):1709-16, 1993

4.McGregor SJ, Erickson AJ. Identification of 5alpha-androst-1-ene-3beta,17beta-diol in the fat of Sus scrofa L.: a "nutritional supplement" not found previously in the food supply. J Nat Prod. 2003 Sep;66(9):1147-8.