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Androstadienone

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, 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 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. 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

References

  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. Retrieved March 14, 2016.
  5. ^ "Human Pheromone Molecules". House of Pheromones. Archived from the original on March 27, 2016. Retrieved March 14, 2016.
  6. ^ Yuhas D (1 May 2014). "Human Sexual Responses Boosted by Bodily Scents". Scientific American. Retrieved March 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.

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