51872-53-8

Usage

InChI:InChI=1/C20H31NO/c1-19-9-7-15(22)11-13(19)3-5-16-17-6-4-14(12-21)20(17,2)10-8-18(16)19/h13-18,22H,3-11H2,1-2H3/t13-,14+,15+,16-,17-,18-,19-,20+/m0/s1

Upstream product

• 53-41-8 cis-androsterone 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Relevant academic research and scientific papers

Neurosteroid Analogues; Structure-Activity Studies of Benzindene Modulators of GABAA Receptor Function. 1. The effect of 6-Methyl Substitution on the Electrophysiological Activity of 7-Substituted Benzindene-3-carbonitriles

The effect of 6-methyl substitution on the ability of 7-(2-hydroxyethyl)benzindene-3-carbonitriles to potentiate GABA-mediated chloride current and to directly gate a chloride current in the absence of GABA in cultured rat hippocampal neurons was investigated.Structurally analogous steroid 17-carbonitriles that either contained or did not contain a 19-methyl group were also investigated.Compounds were evaluated at 1 μM for their ability to potentiate GABA-mediated currents and at 10 μM for current activation in the absence of GABA.The benzindene 3(R)-carbonitriles and analogous steroid 17α-carbonitriles had no effects in either assay.The benzindene-3(S)-carbonitriles and analogous steroid 17β-carbonitriles were active in both assays.Relative to the 6-unsubstituted benzindene 3(S)-carbonitrile, the following effects of 6-methyl substituents were observed: a 6(a)-methyl group increased both activities; a 6(e)-methyl group decreased both activities; and 6,6-dimethyl substituents had opposing effects so that both activites remained similar to those of the 6-unsubstituted compound.The activities of the steroid 17β-carbonitriles were not affected significantly by the presence or absence of a 19-methyl group.A conformational analysis using molecular modeling methods was also performed for the benzindene 3S-carbonitriles and the steroid 17β-carbonitriles.The ability of the different 6-methyl substituents to differentially effect the conformations of the flexible benzindenes and the inability of the steroid 19-methyl group to alter the conformations of the rigid steroid 17β-carbonitriles are suggested to explain the results.

Chemical compounds

Steroids of the androstane series having a 3α-hydroxy group, a 3β-hydrogen or methyl group; a 10-hydrogen atom or methyl group, an 11-oxo group or two hydrogen atoms at the 11-position, a 17α-hydrogen atom, and a group at the 17β-position which is esterified carboxyl group, an N-mono or di-substituted carbamoyl group, a cyano group, a formyl group or an acetalised formyl group; and the 3α-esters thereof. The steroids possess anaesthetic properties.