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Compound

QH-II-66

Also called 7-ethynyl-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one

Original Wikipedia articleen.wikipedia.org/wiki/QH-II-66 revision used (24 October 2026)

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Overview

QH-II-66 (QH-ii-066) is a sedative drug which is a benzodiazepine derivative. It produces some of the same effects as other benzodiazepines, but is much more selective than most other drugs of this class and so produces somewhat less sedation and ataxia than other related drugs such as diazepam and triazolam, although it still retains anticonvulsant effects.[1][2][3] WP

QH-ii-066 is a highly subtype-selective GABAA agonist which was designed to bind selectively to the α₅ subtype of GABAA receptors.[4] WP

The α₅ subtype (and to a lesser extent the α₁ subtype) of GABAA are two of the most important targets in the brain that produce the effects of alcohol, and so one of the purposes for which QH-ii-066 was developed was to reproduce the GABAergic effects of alcohol separately from its other actions.[5][6] WP

QH-ii-066 replicates some of the effects of alcohol, such as sedation and ataxia, but does not increase appetite, as this effect seems to be produced by the α₁ subtype of GABAA rather than α₅. The inverse agonist Ro15-4513, which blocks the α₅ subtype of GABAA, reverses the effects of alcohol, suggesting that this subtype is also important in producing the subjective effects of alcohol intoxication.[7][8] WP

Chemistry

Formula
C18H14N2O PC
CAS number
183239-39-6 PC
Molar mass (g/mol)
274.3 PC
IUPAC name (computed by PubChem)
7-ethynyl-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one PC
SMILES
CN1C(=O)CN=C(C2=C1C=CC(=C2)C#C)C3=CC=CC=C3 PC
InChIKey
FESCSZDQOFYRDR-UHFFFAOYSA-N PC
PubChem CID
9838431
IUPAC name
7-ethynyl-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one WP

Harm reduction information

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Sources

  1. Other Stereospecific anxiolytic and anticonvulsant agents with reduced muscle-relaxant, sedative-hypnotic and ataxic effects
  2. Journal / agency Huang Q, He X, Ma C, Liu R, Yu S, Dayer CA, Wenger GR, McKernan R, Cook JM. Pharmacophore/receptor models for GABAA/BzR subtypes (α₁β₃γ₂, α₅β₃γ₂, and α₆β₃γ₂) via a comprehensive ligand-mapping approach. Journal of Medicinal Chemistry. January 2000. doi:10.1021/jm990341r · PMID 10633039
  3. Other Anxiolytic agents with reduced sedative and ataxic effects
  4. Journal / agency Huang Q, Zhang W, Liu R, McKernan RM, Cook JM. Benzo-fused benzodiazepines employed as topological probes for the study of benzodiazepine receptor subtypes. Medicinal Chemistry Research. 1996
  5. Journal / agency Platt DM, Duggan A, Spealman RD, Cook JM, Li X, Yin W, Rowlett JK. Contribution of alpha 1GABAA and alpha 5GABAA receptor subtypes to the discriminative stimulus effects of ethanol in squirrel monkeys. The Journal of Pharmacology and Experimental Therapeutics. May 2005. doi:10.1124/jpet.104.080275 · PMID 15650112
  6. Journal / agency Hodge CW, Grant KA, Becker HC, Besheer J, Crissman AM, Platt DM, Shannon EE, Shelton KL. Understanding how the brain perceives alcohol: neurobiological basis of ethanol discrimination. Alcoholism: Clinical and Experimental Research. February 2006. doi:10.1111/j.1530-0277.2006.00024.x · PMID 16441269 · PMC11583313
  7. Journal / agency Duke AN, Platt DM, Cook JM, Huang S, Yin W, Mattingly BA, Rowlett JK. Enhanced sucrose pellet consumption induced by benzodiazepine-type drugs in squirrel monkeys: role of GABAA receptor subtypes. Psychopharmacology. August 2006. doi:10.1007/s00213-006-0431-2 · PMID 16783540
  8. Journal / agency Wallner M, Hanchar HJ, Olsen RW. Low-dose alcohol actions on alpha4beta3delta GABAA receptors are reversed by the behavioral alcohol antagonist Ro15-4513. Proceedings of the National Academy of Sciences of the United States of America. May 2006. doi:10.1073/pnas.0600194103 · PMID 16698930 · PMC1482527

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