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Androstadienone chemical structure.png
Systematic (IUPAC) name
CAS Number 4075-07-4 YesY
ATC code None
PubChem CID 92979
ChemSpider 83932 YesY
Chemical data
Formula C19H26O
Molar mass 270.408 g/mol

Androstadienone, also known as androsta-4,16,-dien-3-one, is an endogenous steroid that has been described as having potent pheromone-like activities in humans.[1] The compound is synthesized from androstadienol 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.[2] Androstadienone is related to the androgen sex hormones; however, androstadienone does not exhibit any androgenic or anabolic effects. Though it has been reported to significantly affect the mood of heterosexual women and homosexual men, it does not alter behavior overtly,[3] although it may have more subtle effects on attention.[4] Androstadienone is commonly sold in male fragrances; it is purported to increase sexual attraction.[citation needed]

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  1. ^ Wyart C, Webster WW, Chen JH, Wilson SR, McClary A, Khan RM, Sobel N (February 2007). "Smelling a single component of male sweat alters levels of cortisol in women". J Neurosci 27 (6): 1261–5. doi:10.1523/JNEUROSCI.4430-06.2007. PMID 17287500. 
  2. ^ Joseph Johannes; Agnes Maria Weusten (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina. 
  3. ^ Lundström JN, Olsson MJ (December 2005). "Subthreshold amounts of social odorant affect mood, but not behavior, in heterosexual women when tested by a male, but not a female, experimenter". Biol Psychol 70 (3): 197–204. doi:10.1016/j.biopsycho.2005.01.008. PMID 16242537. 
  4. ^ Hummer TA, McClintock MK (April 2009). "Putative human pheromone androstadienone attunes the mind specifically to emotional information". Horm Behav 55 (4): 548–59. doi:10.1016/j.yhbeh.2009.01.002. PMID 19470369. 

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