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ORG-20599

January 01, 1970

ORG-20599 is a synthetic neuroactive steroid, with sedative effects resulting from its action as a GABAA receptor positive allosteric modulator and, at higher concentrations, agonist.[1][2] It was developed for use as an anaesthetic agent but was never marketed for this purpose, although it is still used in scientific research.[3][4]

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
  • 156685-94-8 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8025739
  • 9850026
  • DTXSID30349651
  • 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 mass 438.04 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

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


 

This sedative-related article is a stub. You can help Wikipedia by expanding it.

January 01, 1970
20599, synthetic, neuroactive, steroid, with, sedative, effects, resulting, from, action, gabaa, receptor, positive, allosteric, modulator, higher, concentrations, agonist, developed, anaesthetic, agent, never, marketed, this, purpose, although, still, used, s. ORG 20599 is a synthetic neuroactive steroid with sedative effects resulting from its action as a GABAA receptor positive allosteric modulator and at higher concentrations agonist 1 2 It was developed for use as an anaesthetic agent but was never marketed for this purpose although it is still used in scientific research 3 4 ORG 20599 Names IUPAC name 2b 3a 5b 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 CAS Number 156685 94 8 Y 3D model JSmol Interactive image ChemSpider 8025739 PubChem CID 9850026 CompTox Dashboard EPA DTXSID30349651 InChI 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 s1Key NZFNABGZEQPYBX PMBZPZLSSA NInChI 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 s1Key NZFNABGZEQPYBX PMBZPZLSBZ SMILES 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 Chemical formula C25H40ClNO3 Molar mass 438 04 g mol Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesChemistry editSee also List of neurosteroidsReferences edit 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 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 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 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 nbsp This sedative related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title ORG 20599 amp oldid 1164683289, wikipedia, wiki, book, books, library,

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