Androstadienone, or androsta-4,16-dien-3-one, is a 16-androstene class

endogenous Endogenous substances and processes are those that originate from within a living system such as an organism, tissue, or cell. In contrast, exogenous substances and processes are those that originate from outside of an organism. For example, es ...

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...

that has been described as having potent

pheromone A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...

-like activities in humans. The compound is synthesized from

androstadienol Androstadienol, or androsta-5,16-dien-3β-ol, is a 16-androstene class endogenous steroid, pheromone, and chemical intermediate to several other pheromones that is found in the sweat of both men and women. Androstadienol and androstadienone ...

by 3β-hydroxysteroid dehydrogenase, and can be converted into

androstenone Androstenone (5α-androst-16-en-3-one) is a 16-androstene class steroidal pheromone. It is found in boar's saliva, celery cytoplasm, and truffle fungus. Androstenone was the first mammalian pheromone to be identified. It is found in high concent ...

(a more potent and odorous pheromone) by

5α-reductase 5α-Reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in three metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism. There are three isozymes of ...

, which can subsequently be converted into 3α-androstenol or 3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase. Androstadienone is related to the

androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This inc ...

sex hormone Sex hormones, also known as sex steroids, gonadocorticoids and gonadal steroids, are steroid hormones that interact with vertebrate steroid hormone receptors. The sex hormones include the androgens, estrogens, and progestogens. Their effects ar ...

s; however, androstadienone does not exhibit any

ic or

anabolic Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-do ...

effects. Though it has been reported to significantly affect the mood of heterosexual women and

homosexual men Gay men are male homosexuals. Some bisexual men, bisexual and homoromantic men may also dually identify as gay, and a number of young gay men also identify as queer. Historically, gay men have been referred to by a number of different terms, ...

, it does not alter behavior overtly, although it may have more subtle effects on attention. Androstadienone is commonly sold in male fragrances; it is purported to increase sexual attraction. Androstadienone, in picogram quantities, has been shown to have "significant reduction of nervousness, tension and other negative feeling states" in female subjects.

References

External links

* Jacob, Tim J.C. (2005) [1999
A critical review of the evidence for the existence (1) human pheromones and (2) a functional vomeronasal organ (VNO) in humans
School of Biosciences, Cardiff University {{Steroid hormones Androstanes Human pheromones Neurosteroids Mammalian pheromones Cyclopentenes

See also

References

External links