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

endogenous Endogeny, in biology, refers to the property of originating or developing from within an organism, tissue, or cell. For example, ''endogenous substances'', and ''endogenous processes'' are those that originate within a living system (e.g. an ...

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

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 (a more potent and odorous pheromone) by 5α-reductase, 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 ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...

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 a ...

s; however, androstadienone does not exhibit any

ic or

anabolic Anabolism () is the set of metabolic pathways that construct macromolecules like DNA or RNA from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catab ...

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

heterosexual Heterosexuality is romantic attraction, sexual attraction, or sexual behavior between people of the opposite sex or gender. As a sexual orientation, heterosexuality is "an enduring pattern of emotional, romantic, and/or sexual attractions ...

women and homosexual men, 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.

See also

References

Further reading