Idazoxan

Idazoxan
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (±)-2-(2,3-dihydro-1,4-benzodioxin-2-yl)-4,5-dihydro-1H-imidazole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H12N2O2
Molar mass204.229 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • C1CN=C(N1)C2COC3=CC=CC=C3O2
  • InChI=1S/C11H12N2O2/c1-2-4-9-8(3-1)14-7-10(15-9)11-12-5-6-13-11/h1-4,10H,5-7H2,(H,12,13) ☒N
  • Key:HPMRFMKYPGXPEP-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Idazoxan (INN) is a drug which is used in scientific research. It acts as both a selective α2 adrenergic receptor antagonist, and an antagonist for the imidazoline receptor. Idazoxan has been under investigation as an antidepressant, but it did not reach the market as such. More recently, it is under investigation as an adjunctive treatment in schizophrenia. Due to its α2 receptor antagonism it is capable of enhancing therapeutic effects of antipsychotics, possibly by enhancing dopamine neurotransmission in the prefrontal cortex of the brain, a brain area thought to be involved in the pathogenesis of schizophrenia.

Alzheimer's research

Mice treated with idazoxan, which blocks the α2A receptor which regulates norepinephrine, behaved similarly to control animals despite still having amyloid-beta plaques in the brain, as a proof-of-concept experiment that dramatically reduced Alzheimer's pathology and symptoms in two mouse models, potentially offering an immediate treatment for this devastating disease.

Synthesis

Note that the literature method claims that the old original patented procedure gives a different reaction product formed through a rearrangement.

Synthesis: Old Patent: New Patent:

The reaction of catechol (1) with 2-Chloroacrylonitrile [920-37-6] (2) gives 2-cyano-1,4-benzodioxan [1008-92-0] (3). Pinner reaction with alcoholic hydrogen chloride leads to the iminoether, (4). Treatment with ethylenediamine [107-15-3] (5) gives the imidazoline ring affording Idazoxin (6).

See also



This page was last updated at 2024-02-11 10:14 UTC. Update now. View original page.

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