3α-Androstanediol

3α-Androstanediol

3α-Androstanediol
Identifiers
CAS number
PubChem
ChemSpider
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)

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.  
  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.  
  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.  
  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.  
  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.  
  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.  
  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.  
  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.  
  9. ^ Reddy DS (March 2004). "Anticonvulsant activity of the testosterone-derived neurosteroid 3alpha-androstanediol". Neuroreport 15 (3): 515–8.  
  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.