Dexoxadrol

Dexoxadrol (Dioxadrol) is a dissociative anaesthetic drug which has been found to be an NMDA antagonist and produces similar effects to PCP in animals. Dexoxadrol, along with another related drug etoxadrol, were developed as analgesics for use in humans, but development was discontinued after patients reported side effects such as nightmares and hallucinations.[1][2]

Dexoxadrol
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: legal
Identifiers
IUPAC name
  • (2S)-2-[(4S)-2,2-di(phenyl)-1,3-dioxolan-4-yl]piperidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H23NO2
Molar mass309.409 g·mol−1
3D model (JSmol)
SMILES
  • O1C[C@@H](OC1(c2ccccc2)c3ccccc3)[C@H]4NCCCC4
InChI
  • InChI=1S/C20H23NO2/c1-3-9-16(10-4-1)20(17-11-5-2-6-12-17)22-15-19(23-20)18-13-7-8-14-21-18/h1-6,9-12,18-19,21H,7-8,13-15H2/t18-,19+/m0/s1 Y
  • Key:HGKAMARNFGKMLC-RBUKOAKNSA-N Y
 NY (what is this?)  (verify)

References
  1. Sax M, Wünsch B (2006). "Relationships between the structure of dexoxadrol and etoxadrol analogues and their NMDA receptor affinity". Current Topics in Medicinal Chemistry. 6 (7): 723–32. doi:10.2174/156802606776894483. PMID 16719812.
  2. Aepkers M, Wünsch B (December 2005). "Structure-affinity relationship studies of non-competitive NMDA receptor antagonists derived from dexoxadrol and etoxadrol". Bioorganic & Medicinal Chemistry. 13 (24): 6836–49. doi:10.1016/j.bmc.2005.07.030. PMID 16169732.
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