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
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ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.313
Chemical and physical data
FormulaC20H28N2O3
Molar mass344.455 g·mol−1
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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] GB 795758 (1958 to Pfizer).

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.



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