Enilospirone

Enilospirone (CERM-3,726) is a selective 5-HT1A receptor agonist of the azapirone class.[1]

Enilospirone
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
IUPAC name
  • 6-(3-chlorophenoxy)-2-methyl-1-oxa-4-azaspiro[4.5]decan-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.056.284
Chemical and physical data
FormulaC15H18ClNO3
Molar mass295.76 g·mol−1

Synthesis
Patent:[2]

Base catalyzed Williamson ether synthesis between 2-chlorocyclohexanone [822-87-7] (1) and 3-Chlorophenol [108-43-0] (2) gives 2-(3-Chlorophenoxy)cyclohexan-1-one [59798-91-3] (3). Condensation with lactic acid (4) and ammonium carbonate gives Enilospirone (5).

See also

References
  1. Maurel JL, Autin JM, Funes P, Newman-Tancredi A, Colpaert F, Vacher B (October 2007). "High-efficacy 5-HT1A agonists for antidepressant treatment: a renewed opportunity". Journal of Medicinal Chemistry. 50 (20): 5024–33. doi:10.1021/jm070714l. PMID 17803293.
  2. DE2542154 idem US4000292 idem Roland Yves Mauvernay et al. U.S. Patent 4,086,352 (1978 to Centre Europeen De Recherches Mauvernay).

Further reading
  • Nicholson AN, Stone BM (1982). "6-(3-chloro)-phenoxy-2-methyl-1-oxa-4-azospiro-[4,5]decane-3-one (CERM 3726) and sleep of healthy men". Psychopharmacology. 76 (2): 157–9. doi:10.1007/BF00435270. PMID 6805026. S2CID 666391.


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