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Androstadienone





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Androstadienone, or androsta-4,16-dien-3-one, is a 16-androstene class endogenous steroid that has been described as having potent pheromone-like activities in humans.[1] The compound is synthesized from androstadienolby3β-hydroxysteroid dehydrogenase, and can be converted into androstenone (a more potent and odorous pheromone) by 5α-reductase, which can subsequently be converted into 3α-androstenolor3β-androstenol (also more potent and odorous pheromones) by 3-ketosteroid reductase.[2]

Androstadienone
Clinical data
ATC code
  • none
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H26O
Molar mass270.416 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C

  • InChI=1S/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3/t15-,16-,17-,18-,19-/m0/s1 checkY

  • Key:HNDHDMOSWUAEAW-VMXHOPILSA-N checkY

 ☒NcheckY (what is this?)  (verify)

Androstadienone is related to the androgen sex hormones; however, androstadienone does not exhibit any androgenicoranabolic 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. Androstadienone, in picogram quantities, has been shown to have "significant reduction of nervousness, tension and other negative feeling states" in female subjects.[8]

See also

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References

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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". The Journal of Neuroscience. 27 (6): 1261–1265. doi:10.1523/JNEUROSCI.4430-06.2007. PMC 6673596. PMID 17287500.
  • ^ Weusten AM (1989). Biochemical pathways in human testicular steroidogenesis (PDF) (Ph.D. thesis). Pressa Trajectina, Universiteit Utrecht.
  • ^ 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". Biological Psychology. 70 (3): 197–204. doi:10.1016/j.biopsycho.2005.01.008. PMID 16242537. S2CID 12401158.
  • ^ Gabrielsen P (2 June 2013). "Mens' [sic] Sweat Pheromone, Androstadienone, Influences Cooperation In Other Men". HuffPost. Retrieved March 14, 2016.
  • ^ "Human Pheromone Molecules". House of Pheromones. Archived from the original on March 27, 2016. Retrieved March 14, 2016.
  • ^ Yuhas D (1 May 2014). "Human Sexual Responses Boosted by Bodily Scents". Scientific American. Retrieved March 14, 2016.
  • ^ Hummer TA, McClintock MK (April 2009). "Putative human pheromone androstadienone attunes the mind specifically to emotional information". Hormones and Behavior. 55 (4): 548–559. doi:10.1016/j.yhbeh.2009.01.002. PMID 19470369. S2CID 17022112.
  • ^ Grosser BI, Monti-Bloch L, Jennings-White C, Berliner DL (April 2000). "Behavioral and electrophysiological effects of androstadienone, a human pheromone". Psychoneuroendocrinology. 25 (3): 289–299. doi:10.1016/s0306-4530(99)00056-6. PMID 10737699. S2CID 41960611.
  • Further reading

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    Retrieved from "https://en.wikipedia.org/w/index.php?title=Androstadienone&oldid=1192238659"
     



    Last edited on 28 December 2023, at 10:40  





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    This page was last edited on 28 December 2023, at 10:40 (UTC).

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