Oxitropium bromide

Oxitropium bromide (trade names Oxivent, Tersigan) is an anticholinergic used as a bronchodilator for the treatment of asthma and chronic obstructive pulmonary disease.^[1]

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	16735948
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

It was patented in 1966 and approved for medical use in 1983.^[2]

It is a thermosalient material.^[3]

Synthesis

Two successive alkylation reactions convert a natural product, norscopolamine (1), into oxitropium bromide. ^[4] The first, with bromoethane, gives an N-ethyl intermediate (2), which is treated with bromomethane.^[5][6][7]