Oxyphencyclimine

Chemical compound

A03AA01 (WHO)

Identifiers

(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

CompTox Dashboard (EPA)

DTXSID4023410

ECHA InfoCard100.004.313

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Chemical and physical dataFormulaC₂₀H₂₈N₂O₃Molar mass344.455 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.^[1]^[2]

References

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

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Drugs for functional gastrointestinal disorders (A03)

Drugs for
functional
bowel
disorders

Antimuscarinics

Tertiary amino group	Oxyphencyclimine Camylofin Mebeverine Trimebutine Rociverine Dicycloverine Dihexyverine Difemerine Piperidolate
Quaternary ammonium compounds	Benzilone Mepenzolate Pipenzolate Glycopyrronium Oxyphenonium Penthienate Methantheline Propantheline Otilonium Tridihexethyl Isopropamide Hexocyclium Poldine Bevonium Diphemanil Tiemonium Prifinium Timepidium Fenpiverinium

Phosphodiesterase
inhibitors

Acting on
serotonin receptors

5-HT₃ antagonists
- Alosetron
- Cilansetron
5-HT₄ agonists
- Mosapride

Other

Belladonna
and derivatives
(antimuscarinics)

Tertiary amines: Atropine
Hyoscyamine

Primarily dopamine antagonists
5-HT₄ agonists
- Cinitapride
- Cisapride

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Muscarinic acetylcholine receptor modulators

mAChRsTooltip Muscarinic acetylcholine receptors

Precursors
(and prodrugs)

See also: Receptor/signaling modulators; Nicotinic acetylcholine receptor modulators; Acetylcholine metabolism/transport modulators

This drug article relating to the gastrointestinal system is a stub. You can help Wikipedia by expanding it.

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