5α-Androst-2-en-17-one

5α-Androst-2-en-17-one is a naturally occurring steroid and pheromone found in humans and other animals. It is a metabolite of the most abundant adrenal androgenic steroid, DHEA, in young adult humans. It is also a precursor of the androgen and estrogen sex hormones.

Chemistry

5α-Androst-2-en-17-one, also known as 5α-androst-2-ene-17-one, is a naturally occurring androstane steroid. It is structurally related to androstenedione, with the difference being the lack of a double bond at the 4,5 position in its A ring.

Biosynthesis and metabolism

5α-Androst-2-en-17-one is synthesized from DHEA in the adrenal glands and the gonads. The conversion is catalyzed by the enzyme 5α-reductase, which reduces the Δ4,5 double bond of DHEA.

In the body, 5α-Androst-2-en-17-one can be converted into more potent androgens such as testosterone and dihydrotestosterone (DHT), or it can be converted into the estrogen estrone.

Biological activity

As a pheromone, 5α-Androst-2-en-17-one has been found to affect mood and sexual behavior in both men and women. It is also thought to play a role in the immune response.

As a steroid, it has weak androgenic activity. It can be converted in the body to more potent androgens, which can stimulate the development and maintenance of male secondary sexual characteristics.

See also

• Androstadienone
• Androstenol
• Androstenone
• Androsterone