Idazoxan

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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
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 (

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.[5]

Synthesis

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

Synthesis:[6][7][8] Old Patent:[9] New Patent:[10]

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,[11] (4). Treatment with ethylenediamine [107-15-3] (5) gives the imidazoline ring affording Idazoxin (6).

See also

References

  1. S2CID 38772290
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  2. PMID 12177687
    .
  3. PMID 2848612
    .
  4. PMID 1939285
    .
  5. PMID 31941827
    .
  6. doi:10.1016/S0040-4039(01)92358-5
    .
  7. doi:10.1002/jhet.5570210117
    .
  8. PMID 6133953
    .
  9. ^ US 2979511, Krapcho J, Lott WA, "Certain 1, 4-benzodioxanyl imidazolines and corresponding pyrimidines and process", issued 11 April 1961, assigned to Olin Corp. 
  10. ^ US 7338970, Bougaret J, Avan JL, Segonds R, "Pharmaceutical composition based on idazoxan, salts, hydrates or polymorphs thereof", issued 3 March 2008, assigned to Pierre Fabre Medicament. 
  11. ^ "2,3-Dihydro-1,4-benzodioxin-2-carbimidic acid ethyl ester". PubChem. U.S. National Library of Medicine. CID:10035919.
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