Tiropramide

Tiropramide is the International nonproprietary name of an antispasmodic drug.^[1]

Tiropramide

Clinical data
Other names	N-[3-[4-(2-Diethylaminoethoxy)phenyl]-1-(dipropylamino)-1-oxopropan-2-yl]benzamide
AHFS/Drugs.com	International Drug Names
ATC code	A03AC05 (WHO)
Identifiers
IUPAC name Nα-benzoyl-O-[2-(diethylamino)ethyl]-N,N-dipropyltyrosinamide
CAS Number	55837-29-1
PubChem CID	42262
ChemSpider	38541
UNII	R7S0904CN2
KEGG	D07087 Y
ChEMBL	ChEMBL2104688
CompTox Dashboard (EPA)	DTXSID70866514
Chemical and physical data
Formula	C28H41N3O3
Molar mass	467.654 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN(CCC)C(=O)C(Cc1ccc(cc1)OCCN(CC)CC)NC(=O)c2ccccc2
InChI InChI=1S/C28H41N3O3/c1-5-18-31(19-6-2)28(33)26(29-27(32)24-12-10-9-11-13-24)22-23-14-16-25(17-15-23)34-21-20-30(7-3)8-4/h9-17,26H,5-8,18-22H2,1-4H3,(H,29,32) Key:FDBWMYOFXWMGEY-UHFFFAOYSA-N
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Synthesis

The acylation of racemic tyrosine (1) with benzoyl chloride gives N,O-dibenzoyl-tyrosine (2). Amide formation with dipropylamine (3) using the mixed anhydride method gives the intermediate (4). Hydrolysis of the phenolic ester with sodium hydroxide forms (5), which is alkylated with ClCH₂CH₂N(CH₂CH₃)₂ to produce the ether tiropramide.^[2][3]