Oxyphencyclimine

Oxyphencyclimine
Systematic (IUPAC) name

(1-Methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	125-53-1^Y
ATC code	A03AA01 (WHO)
PubChem	CID 4642
IUPHAR/BPS	7256
ChemSpider	4481^N
UNII	4V44H1O8XI^N
KEGG	D08325^Y
ChEMBL	CHEMBL1200891^N
Chemical data
Formula	C₂₀H₂₈N₂O₃
Molar mass	344.45 g/mol
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 an antimuscarinic.

Synthesis

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] GB 795758 (1958 to Pfizer).

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

Other

Belladonna
and derivatives
(antimuscarinics)

tertiary amines: Atropine
Hyoscyamine

Propulsives

References

↑ Faust, J. A.; Mori, A.; Sahyun, M. (1959). "Antispasmodics: Esters of Heterocyclic Alcohols". Journal of the American Chemical Society 81 (9): 2214. doi:10.1021/ja01518a051.

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