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ORG-20599

From Wikipedia, the free encyclopedia
ORG-20599
Names
IUPAC name
(2β,3α,5β)-21-chloro-3-hydroxy-2-morpholin-4-ylpregnan-20-one
Other names
2-chloro-1-[(2S,3S,5S,10S,13S)-3-hydroxy-10,13-dimethyl-2-morpholin-4-yl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C25H40ClNO3/c1-24-8-7-19-17(18(24)5-6-20(24)23(29)15-26)4-3-16-13-22(28)21(14-25(16,19)2)27-9-11-30-12-10-27/h16-22,28H,3-15H2,1-2H3/t16-,17-,18-,19-,20+,21-,22-,24-,25-/m0/s1
    Key: NZFNABGZEQPYBX-PMBZPZLSSA-N
  • InChI=1/C25H40ClNO3/c1-24-8-7-19-17(18(24)5-6-20(24)23(29)15-26)4-3-16-13-22(28)21(14-25(16,19)2)27-9-11-30-12-10-27/h16-22,28H,3-15H2,1-2H3/t16-,17-,18-,19-,20+,21-,22-,24-,25-/m0/s1
    Key: NZFNABGZEQPYBX-PMBZPZLSBZ
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CCl)CC[C@@H]4[C@@]3(C[C@@H]([C@H](C4)O)N5CCOCC5)C
Properties
C25H40ClNO3
Molar mass438.04 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

ORG-20599 is a syntheticneuroactive steroid, withsedative effects resulting from its action as aGABAA receptorpositive allosteric modulator and, at higher concentrations,agonist.[1][2] It was developed for use as ananaesthetic agent but was never marketed for this purpose, although it is still used in scientific research.[3][4]

Chemistry

[edit]
See also:List of neurosteroids

References

[edit]
  1. ^Hill-Venning C, Peters JA, Callachan H, Lambert JJ, Gemmell DK, Anderson A, Byford A, Hamilton N, Hill DR, Marshall RJ, Campbell AC. The anaesthetic action and modulation of GABAA receptor activity by the novel water-soluble aminosteroid Org 20599.Neuropharmacology. 1996;35(9-10):1209-22.PMID 9014136
  2. ^Anderson A, Boyd AC, Byford A, Campbell AC, Gemmell DK, Hamilton NM, Hill DR, Hill-Venning C, Lambert JJ, Maidment MS, May V, Marshall RJ, Peters JA, Rees DC, Stevenson D, Sundaram H. Anesthetic activity of novel water-soluble 2 beta-morpholinyl steroids and their modulatory effects at GABAA receptors.Journal of Medicinal Chemistry. 1997 May 23;40(11):1668-81.PMID 9171876
  3. ^Visser SA, Gladdines WW, van der Graaf PH, Peletier LA, Danhof M. Neuroactive steroids differ in potency but not in intrinsic efficacy at the GABA(A) receptor in vivo.Journal of Pharmacology and Experimental Therapeutics. 2002 Nov;303(2):616-26.PMID 12388643
  4. ^Weir CJ, Ling AT, Belelli D, Wildsmith JA, Peters JA, Lambert JJ. The interaction of anaesthetic steroids with recombinant glycine and GABAA receptors.British Journal of Anaesthesia. 2004 May;92(5):704-11.PMID 15033889


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Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
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GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
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GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
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