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3α-Androstanediol

3α-Androstanediol
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IUPAC name
(3R,5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
Other names
Hombreol
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1852-53-5
ChemSpider 15039
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C19H32O2
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3α-Androstanediol (5α-androstane-3α,17β-diol; sometimes abbreviated as 3α-diol) is an endogenous inhibitory androstane neurosteroid and weak antiandrogen, and a major metabolite of dihydrotestosterone (DHT).[1][2][3] As a neurosteroid, it is a potent positive allosteric modulator of the GABAA receptor,[4] and is known to have rewarding,[5][6] anxiolytic,[7] prosexual,[8] and anticonvulsant effects.[9][10] As androgens such as testosterone and DHT are known to have many of the same effects and are metabolized into 3α-androstanediol, it is thought that this compound may in part be responsible for said effects via its neurosteroid action.[5][6][7][10]

See also

References

  1. Reddy DS (2010). "Neurosteroids: endogenous role in the human brain and therapeutic potentials". Prog. Brain Res. 186: 113–37. PMC 3139029. PMID 21094889. doi:10.1016/B978-0-444-53630-3.00008-7. 
  2. Jin Y, Penning TM (March 2001). "Steroid 5alpha-reductases and 3alpha-hydroxysteroid dehydrogenases: key enzymes in androgen metabolism". Best Pract. Res. Clin. Endocrinol. Metab. 15 (1): 79–94. PMID 11469812. doi:10.1053/beem.2001.0120. 
  3. Penning TM, Bauman DR, Jin Y, Rizner TL (February 2007). "Identification of the molecular switch that regulates access of 5alpha-DHT to the androgen receptor". Mol. Cell. Endocrinol. 265-266: 77–82. PMC 1857325. PMID 17223255. doi:10.1016/j.mce.2006.12.007. 
  4. Reddy DS, Jian K (September 2010). "The testosterone-derived neurosteroid androstanediol is a positive allosteric modulator of GABAA receptors". J. Pharmacol. Exp. Ther. 334 (3): 1031–41. PMC 2939675. PMID 20551294. doi:10.1124/jpet.110.169854. 
  5. 5.0 5.1 Frye CA (February 2007). "Some rewarding effects of androgens may be mediated by actions of its 5alpha-reduced metabolite 3alpha-androstanediol". Pharmacol. Biochem. Behav. 86 (2): 354–67. PMC 1857333. PMID 17112575. doi:10.1016/j.pbb.2006.10.003. 
  6. 6.0 6.1 Rosellini RA, Svare BB, Rhodes ME, Frye CA (November 2001). "The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference". Brain Res. Brain Res. Rev. 37 (1-3): 162–71. PMID 11744084. doi:10.1016/s0165-0173(01)00116-3. 
  7. 7.0 7.1 Fernández-Guasti A, Martínez-Mota L (September 2005). "Anxiolytic-like actions of testosterone in the burying behavior test: role of androgen and GABA-benzodiazepine receptors". Psychoneuroendocrinology 30 (8): 762–70. PMID 15919582. doi:10.1016/j.psyneuen.2005.03.006. 
  8. Sánchez Montoya EL, Hernández L, Barreto-Estrada JL, Ortiz JG, Jorge JC (November 2010). "The testosterone metabolite 3α-diol enhances female rat sexual motivation when infused in the nucleus accumbens shell". J Sex Med 7 (11): 3598–609. PMID 20646182. doi:10.1111/j.1743-6109.2010.01937.x. 
  9. Reddy DS (March 2004). "Anticonvulsant activity of the testosterone-derived neurosteroid 3alpha-androstanediol". Neuroreport 15 (3): 515–8. PMID 15094514. doi:10.1097/00001756-200403010-00026. 
  10. 10.0 10.1 Reddy DS (2004). "Testosterone modulation of seizure susceptibility is mediated by neurosteroids 3alpha-androstanediol and 17beta-estradiol". Neuroscience 129 (1): 195–207. PMID 15489042. doi:10.1016/j.neuroscience.2004.08.002.