oxyphencyclimine

Also 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.

In the Vinony graph

Within Vinony's link graph, oxyphencyclimine is referenced by 458 other articles, and connects out to atropine, L-scopolamine and muscarinic acetylcholine receptor family.

It is catalogued under topics including Chemical pages without DrugBank identifier, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Its subject is documented across 6 Wikipedia language editions.

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 Å²
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

Sources (4)

via Wikidata · CC0

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Encyclopedic overview

2 sections

Contents

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.