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KRM-II-81







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KRM-II-81[1]

Names

IUPAC name

5-(8-Ethynyl-6-pyridin-2-yl-4H-imidazo[1,5-a][1,4]benzodiazepin-3-yl)-1,3-oxazole

Identifiers

3D model (JSmol)

ChEMBL

ChemSpider

PubChem CID

  • InChI=1S/C21H13N5O/c1-2-14-6-7-17-15(9-14)20(16-5-3-4-8-23-16)24-10-18-21(25-12-26(17)18)19-11-22-13-27-19/h1,3-9,11-13H,10H2

    Key: KNCUEWYWBUIFTQ-UHFFFAOYSA-N

  • C#CC1=CC2=C(C=C1)N3C=NC(=C3CN=C2C4=CC=CC=N4)C5=CN=CO5

Properties

Chemical formula

C21H13N5O

Molar mass

351.369 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

KRM-II-81 is a positive allosteric modulator of the GABAA receptor. It is selective for the alpha2 and alpha3 subunits. KRM-II-81 displays anxiolytic, antidepressant and anticonvulsant effects. However, it has less adverse effects than some other GABAA PAMs: it has low to no sedation and no tolerance development.[2]

A study has also shown KRM-II-81 to be better at treating seizures than diazepam.[3]

References[edit]

  1. ^ "KRM-II-81".
  • ^ Witkin, Jeffrey M.; Lippa, Arnold; Smith, Jodi L.; Jin, Xiaoming; Ping, Xingjie; Biggerstaff, Andrew; Kivell, Bronwyn M.; Knutson, Daniel E.; Sharmin, Dishary; Pandey, Kamal P.; Mian, Md Yeunus; Cook, James M.; Cerne, Rok (February 2022). "The imidazodiazepine, KRM-II-81: An example of a newly emerging generation of GABAkines for neurological and psychiatric disorders". Pharmacology, Biochemistry, and Behavior. 213: 173321. doi:10.1016/j.pbb.2021.173321. ISSN 1873-5177. PMID 35041859. S2CID 245963990.
  • ^ Knutson, Daniel E.; Smith, Jodi L.; Ping, Xingjie; Jin, Xiaoming; Golani, Lalit K.; Li, Guanguan; Tiruveedhula, V. V. N. Phani Babu; Rashid, Farjana; Mian, Md Yeunus; Jahan, Rajwana; Sharmin, Dishary; Cerne, Rok; Cook, James M.; Witkin, Jeffrey M. (2020-09-02). "Imidazodiazepine Anticonvulsant, KRM-II-81, Produces Novel, Non-diazepam-like Antiseizure Effects". ACS Chemical Neuroscience. 11 (17): 2624–2637. doi:10.1021/acschemneuro.0c00295. hdl:1805/28047. ISSN 1948-7193. PMID 32786313. S2CID 221123396.
  • Alcohols

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  • Methanol
  • Methylpentynol
  • Pentanol
  • Petrichloral
  • Propanol
  • tert-Butanol (2M2P)
  • tert-Pentanol (2M2B)
  • Tribromoethanol
  • Trichloroethanol
  • Triclofos
  • Trifluoroethanol
  • Barbiturates

  • Allobarbital
  • Alphenal
  • Amobarbital
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  • Methylphenobarbital
  • Narcobarbital
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  • Phetharbital
  • Primidone
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  • Ro48-6791
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  • SH-053-R-CH3-2′F
  • Sulazepam
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  • See also: Receptor/signaling modulatorsGABA receptor modulatorsGABA metabolism/transport modulators

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