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26095-59-0

Basic Information
CAS No.: 26095-59-0
Name: Otilonium bromide
Molecular Structure:
Molecular Structure of 26095-59-0 (Otilonium bromide)
Formula: C29H43BrN2O4
Molecular Weight: 563.575
Synonyms: Ethanaminium,N,N-diethyl-N-methyl-2-[[4-[[2-(octyloxy)benzoyl]amino]benzoyl]oxy]-, bromide(1:1);Ammonium,diethyl(2-hydroxyethyl)methyl-, bromide, p-[o-(octyloxy)benzamido]benzoate(8CI);Benzoic acid, p-[o-(octyloxy)benzamido]-, ester withdiethyl(2-hydroxyethyl)methylammonium bromide (8CI);Otiloniumbromide;SP 63;Spasmomen;
EINECS: 247-457-4
Melting Point: 130-133 °C
Appearance: white power
PSA: 64.63000
LogP: 3.39840
Synthetic route
74-83-9

methyl bromide

26090-29-9

4-(2-Octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

26095-59-0

otilonium bromide

Conditions
ConditionsYield
In acetone at 60℃; for 48h; Reflux; Sealed tube; Inert atmosphere;33%
119-36-8

methyl salicylate

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 85 °C / Sealed tube; Inert atmosphere
2: sodium hydroxide / methanol; tetrahydrofuran; water / 20 - 85 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / Inert atmosphere
5: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
111-83-1

1-bromo-octane

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 85 °C / Sealed tube; Inert atmosphere
2: sodium hydroxide / methanol; tetrahydrofuran; water / 20 - 85 °C
3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere
4: triethylamine / dichloromethane / Inert atmosphere
5: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
100-37-8

2-(Diethylamino)ethanol

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; triethylamine / dichloromethane / 0.5 h / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 760.05 Torr
3: triethylamine / dichloromethane / Inert atmosphere
4: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
122-04-3

4-nitro-benzoyl chloride

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dmap; triethylamine / dichloromethane / 0.5 h / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 760.05 Torr
3: triethylamine / dichloromethane / Inert atmosphere
4: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
255062-85-2

2-octyloxybenzoic acid methyl ester

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / methanol; tetrahydrofuran; water / 20 - 85 °C
2: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere
3: triethylamine / dichloromethane / Inert atmosphere
4: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
27830-12-2

2-octyloxybenzoic acid

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere
2: triethylamine / dichloromethane / Inert atmosphere
3: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
13456-39-8

2-(diethylamino)ethyl 4-nitrobenzoate

26095-59-0

otilonium bromide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium 10% on activated carbon / ethanol / 20 °C / 760.05 Torr
2: triethylamine / dichloromethane / Inert atmosphere
3: acetone / 48 h / 60 °C / Reflux; Sealed tube; Inert atmosphere
View Scheme
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Chemistry

Molecule structure of Otilonium bromide (CAS NO.26095-59-0):

IUPAC Name: Diethyl-methyl-[2-[4-[(2-octoxybenzoyl)amino]benzoyl]oxyethyl]azanium bromide 
Molecular Weight: 563.56672 g/mol
Molecular Formula: C29H43BrN2O4 
Melting Point: 130-133 °C
Appearance: white powder
H-Bond Donor: 1
H-Bond Acceptor: 5
Rotatable Bond Count: 17
Tautomer Count: 4
Exact Mass: 562.24062
MonoIsotopic Mass: 562.24062
Topological Polar Surface Area: 64.6
Heavy Atom Count: 36
Canonical SMILES: CCCCCCCCOC1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C(=O)OCC[N+](C)(CC)CC.[Br-]
InChI: InChI=1S/C29H42N2O4.BrH/c1-5-8-9-10-11-14-22-34-27-16-13-12-15-26(27)28(32)30-25-19-17-24(18-20-25)29(33)35-23-21-31(4,6-2)7-3;/h12-13,15-20H,5-11,14,21-23H2,1-4H3;1H
InChIKey: VWZPIJGXYWHBOW-UHFFFAOYSA-N
EINECS: 247-457-4
Product Categories: Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals

Uses

 Otilonium bromide (CAS NO.26095-59-0) can be used as inhibits platlet activating factor induced hypotension and antispasmodic.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 intraperitoneal 85mg/kg (85mg/kg)   Farmaco, Edizione Scientifica. Vol. 39, Pg. 3, 1984.
 
mammal (species unspecified) LD50 oral 650mg/kg (650mg/kg)   Farmaco, Edizione Scientifica. Vol. 39, Pg. 3, 1984.
 
mammal (species unspecified) LD50 subcutaneous 1gm/kg (1000mg/kg)   Farmaco, Edizione Scientifica. Vol. 39, Pg. 3, 1984.
 
mouse LD50 intravenous 46500ug/kg (46.5mg/kg)   Medicamentos de Actualidad. Vol. 15, Pg. 417, 1979.
mouse LD50 oral > 1500mg/kg (1500mg/kg)   Medicamentos de Actualidad. Vol. 15, Pg. 417, 1979.
rat LD50 intravenous 14100ug/kg (14.1mg/kg)   Medicamentos de Actualidad. Vol. 15, Pg. 417, 1979.
rat LD50 oral > 1650mg/kg (1650mg/kg)   Medicamentos de Actualidad. Vol. 15, Pg. 417, 1979.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. When heated to decomposition it emits toxic fumes of Br and NOx.

Specification

 Otilonium bromide (CAS NO.26095-59-0) is also named as Bromure d'otilonium ; Bromure d'otilonium [INN-French] ; Bromuro de otilonio ; Bromuro de otilonio [INN-Spanish] ; Diethyl(2-hydroxyethyl)methylammonium bromide p-(o-
(octyloxy)benzamido)-benzoate ; Diethyl(2-hydroxyethyl)methylammonium bromide p-(o-(octyloxy)benzamido)benzoate ;
Ethanaminium, N,N-diethyl-N-methyl-2-((4-((2-(octyloxy)benzoyl)amino)benzoyl)oxy)-, bromide ; Octylonium bromide ; Otilonii bromidum ; Otilonii bromidum [INN-Latin] ; Ottilonio bromuro ; Ottilonio bromuro [Italian] ; SP63 ; Spasmomen ; UNII-21HN3N72PV . Otilonium bromide (CAS NO.26095-59-0) is an antimuscarinic.