3α-Androstanediol

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3α-Androstanediol
3alpha-androstanediol.png
Identifiers
CAS number 1852-53-5
PubChem 15818
ChemSpider 15039
Jmol-3D images Image 1
Properties
Molecular formula C19H32O2
Molar mass 292.46 g/mol
Except where noted otherwise, 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[edit]

References[edit]

  1. ^ Reddy DS (2010). "Neurosteroids: endogenous role in the human brain and therapeutic potentials". Prog. Brain Res. 186: 113–37. doi:10.1016/B978-0-444-53630-3.00008-7. PMC 3139029. PMID 21094889. 
  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. doi:10.1053/beem.2001.0120. PMID 11469812. 
  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. doi:10.1016/j.mce.2006.12.007. PMC 1857325. PMID 17223255. 
  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. doi:10.1124/jpet.110.169854. PMC 2939675. PMID 20551294. 
  5. ^ a b 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. doi:10.1016/j.pbb.2006.10.003. PMC 1857333. PMID 17112575. 
  6. ^ a b 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. 
  7. ^ a b 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. doi:10.1016/j.psyneuen.2005.03.006. PMID 15919582. 
  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. doi:10.1111/j.1743-6109.2010.01937.x. PMID 20646182. 
  9. ^ Reddy DS (March 2004). "Anticonvulsant activity of the testosterone-derived neurosteroid 3alpha-androstanediol". Neuroreport 15 (3): 515–8. PMID 15094514. 
  10. ^ a b Reddy DS (2004). "Testosterone modulation of seizure susceptibility is mediated by neurosteroids 3alpha-androstanediol and 17beta-estradiol". Neuroscience 129 (1): 195–207. doi:10.1016/j.neuroscience.2004.08.002. PMID 15489042.