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Chemical compound
Oxyphencyclimine
AHFS /
Drugs.com
International Drug Names
ATC code
(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 InfoCard
100.004.313
Formula C 20 H 28 N 2 O 3
Molar mass 344.455 g·mol−1
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
N Y
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Oxyphencyclimine is a
muscarinic receptor antagonist , given orally to treat
peptic ulcer disease and gastrointestinal
spasms . It has
antispasmodic and
antimotility properties.
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]
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