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Alaproclate

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Alaproclate
File:Alaproclate structure.svg
Systematic (IUPAC) name
1-(4-chlorophenyl)-2-methylpropan-2-yl 2-aminopropanoate
Clinical data
  • Uncontrolled
Oral
Identifiers
60719-82-6 7pxN
60719-83-7 (hydrochloride)
N06AB07
PubChem CID 2081
ChemSpider 1997 7pxY
UNII C4R42570ZO 7pxY
KEGG D02787 7pxY
ChEMBL CHEMBL36591 7pxY
Chemical data
Formula C13H18ClNO2
255.740 g/mol
 14pxN (what is this?)  (verify)

Alaproclate (GEA-654) is a psychoactive drug and research chemical that was being developed as an antidepressant by the Swedish pharmaceutical company Astra AB (now AstraZeneca) in the 1970s. It acts as a selective serotonin reuptake inhibitor (SSRI), and along with zimelidine and indalpine, was one of the first of its kind. Development was discontinued due to the observation of liver complications in rodent studies. Some studies have found that it acts as a noncompetitive NMDA antagonist, but does not have discriminative stimulus properties similar to phencyclidine.[1][2]

Synthesis

File:Alaproclate synthesis.png
Alaproclate synthesis:[3]

See also

References

  1. ^ Wilkinson A, Courtney M, Westlind-Danielsson A, Hallnemo G, Akerman KE (December 1994). "Alaproclate acts as a potent, reversible and noncompetitive antagonist of the NMDA receptor coupled ion flow". The Journal of Pharmacology and Experimental Therapeutics 271 (3): 1314–9. PMID 7996440. (subscription required (help)). 
  2. ^ Nicholson KL, Balster RL (November 2003). "Evaluation of the phencyclidine-like discriminative stimulus effects of novel NMDA channel blockers in rats". Psychopharmacology (Berlin) 170 (2): 215–24. PMID 12851738. doi:10.1007/s00213-003-1527-6. (subscription required (help)). 
  3. ^ Lindberg, Ulf Henrik (1978). "Inhibitors of neuronal monoamine uptake. 2. Selective inhibition of 5-hydroxytryptamine uptake by .alpha.-amino acid esters of phenethyl alcohols". Journal of Medicinal Chemistry 21 (5): 448–456. doi:10.1021/jm00203a008.  edit


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