Chemistry:Oxyphencyclimine

Short description: Chemical compound

Oxyphencyclimine

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A03AA01 (WHO)
Identifiers
IUPAC name (1-Methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
CAS Number	125-53-1 Y
PubChem CID	4642
IUPHAR/BPS	7256
ChemSpider	4481 N
UNII	4V44H1O8XI
KEGG	D08325 Y
ChEMBL	ChEMBL1200891 N
Chemical and physical data
Formula	C20H28N2O3
Molar mass	344.455 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)

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.