Oxitropium bromide

Oxitropium bromide

Clinical data
Trade names	Oxivent, Tersigan, Tersigat, Ventilat
Other names	N-Ethylscopolammonium bromide; Ba 253; Ba 253BR-L; Ba 253Br; Hyoscine ethobromide; N-Ethylnorscopolamine methyl bromide; Scopolamine ethobromide
AHFS/Drugs.com	International Drug Names
ATC code	R03BB02 (WHO)
Identifiers
IUPAC name (8r)-6β,7β-Epoxy-8-ethyl-3α-hydroxy-1αH,5αH-tropanium bromide (−)-tropate
CAS Number	30286-75-0
ChemSpider	16738638
UNII	SF4NW7NH7C
ChEMBL	ChEMBL1697846
CompTox Dashboard (EPA)	DTXSID0023402
ECHA InfoCard	100.045.543
Chemical and physical data
Formula	C19H26BrNO4
Molar mass	412.324 g·mol−1
3D model (JSmol)	Interactive image
SMILES [Br-].OC[C@H](c1ccccc1)C(=O)O[C@@H]2C[C@@H]3[C@H]4O[C@H]4[C@H](C2)[N ]3(C)CC
InChI InChI=1S/C19H26NO4.BrH/c1-3-20(2)15-9-13(10-16(20)18-17(15)24-18)23-19(22)14(11-21)12-7-5-4-6-8-12;/h4-8,13-18,21H,3,9-11H2,1-2H3;1H/q 1;/p-1/t13-,14-,15-,16 ,17-,18 ,20?;/m1./s1 Key:LCELQERNWLBPSY-KHSTUMNDSA-M

Oxitropium bromide (trade names Oxivent, Tersigan) is an anticholinergic used as a bronchodilator for the treatment of asthma and chronic obstructive pulmonary disease.

It was patented in 1966 and approved for medical use in 1983.

Synthesis

The natural product, norscopolamine (1), is converted by two alkylation reactions into oxitropium bromide. The first, with bromoethane, gives the N-ethyl intermediate (2), which is treated with bromomethane.