Androstadienone

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Androstadienone
Androstadienone chemical structure.png
Clinical data
ATC code none
Identifiers
IUPAC name: (8S,9S,10R,13R,14S)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one
CAS Number 4075-07-4 YesY
PubChem (CID) 92979
ChemSpider 83932 YesY
UNII ZUZ4FHD36E N
Chemical and physical data
Formula C19H26O
Molar mass 270.408 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

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][4][5][6] although it may have more subtle effects on attention.[7] Androstadienone is commonly sold in male fragrances; it is purported to increase sexual attraction, but there is no convincing evidence of its effectiveness.[8] Androstadienone, in picogram quantities, has been shown to have "significant reduction of nervousness, tension and other negative feeling states" in female subjects.[9]

See also[edit]

References[edit]

  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. ^ "Mens' Sweat Pheromone, Androstadienone, Influences Cooperation In Other Men". Retrieved March 14, 2016. 
  5. ^ "Human Pheromone Molecules". Archived from the original on March 14, 2016. Retrieved March 14, 2016. 
  6. ^ "Human Sexual Responses Boosted by Bodily Scents". Retrieved March 14, 2016. 
  7. ^ 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. 
  8. ^ Woolston, Chris (2007-07-16). "Pheromones in your cologne? Good luck". Los Angeles Times. ISSN 0458-3035. Retrieved 2016-05-27. 
  9. ^ Grosser, B. "Behavioral and electrophysiological effects of androstadienone, a human pheromone.". PubMed. US National Library of Medicine National Institutes of Health. Retrieved March 23, 2016. 

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