Oxyphencyclimine

Oxyphencyclimine is a muscarinic receptor antagonist, given orally to treat peptic ulcer disease and gastrointestinal spasms. It has antispasmodic and antimotility properties.

Oxyphencyclimine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC20H28N2O3
Molar mass344.455 g·mol−1
InChI
  • 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
 NY (what is this?)  (verify)

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.



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