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Structure via PubChem · Public domain (PubChem)
oxyphencyclimine
Sign in to saveAlso known as Oxifencicliminum, Oxyphencycliminum
Oxyphencyclimine is a muscarinic receptor antagonist, given orally to treat peptic ulcer disease and gastrointestinal spasms. It has antispasmodic and antimotility properties.
Chemical data
- Formula
- C20H28N2O3
- Molecular weight
- 344.4 g/mol
- IUPAC name
- (1-methyl-5,6-dihydro-4H-pyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
- SMILES
- CN1CCCN=C1COC(=O)C(C2CCCCC2)(C3=CC=CC=C3)O
- InChIKey
- DUDKAZCAISNGQN-UHFFFAOYSA-N
- XLogP
- 2.9
- Polar surface area
- 62.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- oral
- Indications
- gastrointestinal disease
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 344.21
- Has use
- medication
Show 3 more facts
- chemical formula
- C₂₀H₂₈N₂O₃
- canonical SMILES
- CN1CCCN=C1COC(=O)C(C2CCCCC2)(C3=CC=CC=C3)O
- defined daily dose
- 20.0
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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).
Excerpted from Wikipedia’s “oxyphencyclimine” article, available under the CC BY-SA 4.0 licence.