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Azaloxan

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Chemical compound Pharmaceutical compound
Azaloxan
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 1-(1-{2-ethyl}piperidin-4-yl)imidazolidin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H25N3O3
Molar mass331.416 g·mol
3D model (JSmol)
SMILES
  • O=C1NCCN1C2CCN(CC2)CC3Oc4c(OC3)cccc4
InChI
  • InChI=1S/C18H25N3O3/c22-18-19-8-12-21(18)14-5-9-20(10-6-14)11-7-15-13-23-16-3-1-2-4-17(16)24-15/h1-4,14-15H,5-13H2,(H,19,22)/t15-/m0/s1
  • Key:CDFTVVPIMLXJRX-HNNXBMFYSA-N
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Azaloxan (CGS-7135A) is a drug which was patented as an antidepressant by Ciba-Geigy in the early 1980s, but was never marketed.

Synthesis

Thymoleptic described as a “psychostimulant” according to patent title.

Patent:

The halogenation of allyl cyanide (1) with bromine gives 3,4-dibromobutyronitrile (2). This is further reacted with catechol (3) to give the 1,4-benzodioxan-2-yl-acetonitrile (4). Acid catalyzed hydrolysis of the nitrile to the acid gives 1,4-benzodioxan-2-yl-acetic acid (5). The reduction of this to alcohol with sodium bis(2-methoxyethoxy)aluminium hydride gives 2-(1,4-benzodioxan-2-yl)ethanol (6). The tosylation of this intermediate gives CID:12850582 (7). The synthesis concludes with an SN-2 displacement reaction with 1-(4-piperidinyl)-2-imidazolidinone (8) completing the synthesis of Azaloxan (9).

See also

References

  1. Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
  2. Charles F. Huebner, U.S. patent 4,329,348 (1982 to Ciba-Geigy Corporation).


Antidepressants (N06A)
Specific reuptake inhibitors and/or receptor modulators
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
Tricyclic and tetracyclic antidepressants
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Monoamine oxidase inhibitors
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Adjunctive therapies
Miscellaneous
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