Oxyphencyclimine

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Oxyphencyclimine
Oxyphencyclimine.png
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (1-Methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.313 Edit this at Wikidata
Chemical and physical data
FormulaC20H28N2O3
Molar mass344.455 g·mol−1
  • InChI=1S/C20H28N2O3/c1-22-14-8-13-21-18(22)15-25-19(23)20(24,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2,4-5,9-10,17,24H,3,6-8,11-15H2,1H3 ☒N
  • Key:DUDKAZCAISNGQN-UHFFFAOYSA-N ☒N
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Oxyphencyclimine is a muscarinic receptor antagonist, given orally to treat peptic ulcer disease and gastrointestinal spasms. It has antispasmodic and antimotility properties.

Synthesis

The reaction of chloroacetonitrile (1) with methanol and hydrogen chloride leads to the corresponding iminoether (Pinner reaction). Condensation of 2 with 3-methylaminopropylamine gives (3) gives the corresponding tetrahydropyrimidine (4). Displacement of the halogen with the sodium salt 5 affords oxyphencyclimine (6).

Oxyphencyclimine synthesis.[1][2]

References

  1. ^ Faust JA, Mori A, Sahyun M (1959). "Antispasmodics: Esters of Heterocyclic Alcohols". Journal of the American Chemical Society. 81 (9): 2214. doi:10.1021/ja01518a051.
  2. ^ GB 795758, "Amino esters and the preparation thereof", published 1958-05-28, assigned to Charles Pfizer & Co. Inc.