Androstadienone

Androstadienone

Systematic (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
Identifiers
CAS Number	4075-07-4
ATC code	none
PubChem	CID 92979
ChemSpider	83932
Chemical data
Formula	C19H26O
Molar mass	270.408 g/mol
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CCC4=CC(=O)CC[C@]34C
InChI 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 Key:HNDHDMOSWUAEAW-VMXHOPILSA-N
(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. 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

• Androstadienol
• Androstenone
• Androstenol
• Androsterone
• Estratetraenol

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". 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. 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.

External links

• A critical review of the evidence for the existence (1) human pheromones and (2) a functional vomeronasal organ (VNO) in humans