Cannabaceae

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Not to be confused with 5α-Dihydrotestosterone.
5β-Dihydrotestosterone
Names
IUPAC name
17β-Hydroxy-5β-androstan-3-one
Systematic IUPAC name
(1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-Hydroxy-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.933 Edit this at Wikidata
UNII
  • C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
Properties
C19H30O2
Molar mass 290.447 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5β-Dihydrotestosterone (5β-DHT), also known as 5β-androstan-17β-ol-3-one or as etiocholan-17β-ol-3-one, is an etiocholane (5β-androstane) steroid as well as an inactive metabolite of testosterone formed by 5β-reductase in the liver and bone marrow[1][2] and an intermediate in the formation of 3α,5β-androstanediol and 3β,5β-androstanediol (by 3α- and 3β-hydroxysteroid dehydrogenase) and, from them, respectively, etiocholanolone and epietiocholanolone (by 17β-hydroxysteroid dehydrogenase).[3][4] Unlike its isomer 5α-dihydrotestosterone (5α-DHT or simply DHT), 5β-DHT either does not bind to or binds only very weakly to the androgen receptor.[1] 5β-DHT is notable among metabolites of testosterone in that, due to the fusion of the A and B rings in the cis orientation, it has an extremely angular molecular shape, and this could be related to its lack of androgenic activity.[5] 5β-DHT, unlike 5α-DHT, is also inactive in terms of neurosteroid activity,[6][7] although its metabolite, etiocholanolone, does possess such activity.[8][9]

See also

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References

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  1. ^ a b Hormones, Brain and Behavior Online. Academic Press. 18 June 2002. pp. 2262–. ISBN 978-0-08-088783-8.
  2. ^ H.-J. Bandmann; R. Breit; E. Perwein (6 December 2012). Klinefelter's Syndrome. Springer Science & Business Media. pp. 293–. ISBN 978-3-642-69644-2.
  3. ^ Shlomo Melmed; Kenneth S. Polonsky; P. Reed Larsen; Henry M. Kronenberg (30 November 2015). Williams Textbook of Endocrinology. Elsevier Health Sciences. pp. 711–. ISBN 978-0-323-29738-7.
  4. ^ Anita H. Payne; Matthew P. Hardy (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 186–. ISBN 978-1-59745-453-7.
  5. ^ B.A. Cooke; H.J. Van Der Molen; R.J.B. King (1 November 1988). Hormones and their Actions. Elsevier. pp. 173–. ISBN 978-0-08-086077-0.
  6. ^ Current Topics in Membranes and Transport. Academic Press. 1 February 1988. pp. 169–. ISBN 978-0-08-058502-4.
  7. ^ Abraham Weizman (1 February 2008). Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment. Springer Science & Business Media. pp. 210–. ISBN 978-1-4020-6854-6.
  8. ^ Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G (June 2007). "Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor". Mol. Pharmacol. 71 (6): 1582–90. doi:10.1124/mol.106.033407. PMC 3788649. PMID 17341652.
  9. ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA (June 2005). "Anticonvulsant activity of androsterone and etiocholanolone". Epilepsia. 46 (6): 819–27. doi:10.1111/j.1528-1167.2005.00705.x. PMC 1181535. PMID 15946323.


source: https://en.wikipedia.org/wiki/5%CE%B2-Dihydrotestosterone

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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