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Androstadienone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
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, orandrosta-4,16-dien-3-one, is a16-androstene classendogenoussteroid that has been described as having potentpheromone-like activities in humans.[1] The compound issynthesized fromandrostadienol by3β-hydroxysteroid dehydrogenase, and can be converted intoandrostenone (a more potent and odorous pheromone) by5α-reductase, which can subsequently be converted into3α-androstenol or3β-androstenol (also more potent and odorous pheromones) by3-ketosteroid reductase.[2]

Androstadienone is related to theandrogensex hormones; however, androstadienone does not exhibit anyandrogenic oranabolic effects. Though it has been reported to significantly affect the mood ofheterosexual women andhomosexual 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

[edit]

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.
  2. ^Weusten AM (1989).Biochemical pathways in human testicular steroidogenesis(PDF) (Ph.D. thesis). Pressa Trajectina, Universiteit Utrecht.
  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".Biological Psychology.70 (3):197–204.doi:10.1016/j.biopsycho.2005.01.008.PMID 16242537.S2CID 12401158.
  4. ^Gabrielsen P (2 June 2013)."Mens' [sic] Sweat Pheromone, Androstadienone, Influences Cooperation In Other Men".HuffPost. RetrievedMarch 14, 2016.
  5. ^"Human Pheromone Molecules".House of Pheromones. Archived fromthe original on March 27, 2016. RetrievedMarch 14, 2016.
  6. ^Yuhas D (1 May 2014)."Human Sexual Responses Boosted by Bodily Scents".Scientific American. RetrievedMarch 14, 2016.
  7. ^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.
  8. ^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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Pheromones
Steroids
Volatileamines
Pherines
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
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