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Oxyphencyclimine

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Chemical compound
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Pharmaceutical compound
Oxyphencyclimine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (1-Methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.313Edit this at Wikidata
Chemical and physical data
FormulaC20H28N2O3
Molar mass344.455 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
 ☒NcheckY (what is this?)  (verify)

Oxyphencyclimine is amuscarinic receptor antagonist, given orally to treatpeptic ulcer disease and gastrointestinalspasms. It hasantispasmodic andantimotility properties.

Synthesis

[edit]

The reaction ofchloroacetonitrile (1) withmethanol andhydrogen chloride leads to the corresponding iminoether (Pinner reaction). Condensation of2 with 3-methylaminopropylamine gives (3) gives the correspondingtetrahydropyrimidine (4). Displacement of the halogen with the sodium salt5 affords oxyphencyclimine (6).

Oxyphencyclimine synthesis.[1][2]

References

[edit]
  1. ^Faust JA, Mori A, Sahyun M (1959). "Antispasmodics: Esters of Heterocyclic Alcohols".Journal of the American Chemical Society.81 (9):2214–2219.doi:10.1021/ja01518a051.
  2. ^GB 795758, "Amino esters and the preparation thereof", published 1958-05-28, assigned toCharles Pfizer & Co. Inc. 


Drugs for
functional
bowel
disorders
Antimuscarinics
Tertiary
amino group
Quaternary
ammonium

compounds
Phosphodiesterase
inhibitors
Acting on
serotonin receptors
Other
Belladonna
and derivatives
(antimuscarinics)
Propulsives
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(andprodrugs)


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