Ambroxol

Ambroxol Basic information
Product Name:Ambroxol
Synonyms:4-((2-amino-3,5-dibromobenzyl)amino)-(e)-cyclohexano;5-dibromophenyl)methyl)amino)-4-(((2-amino-trans-cyclohexano;Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)- (E)-;Cyclohexanol, 4-[[(2-amino-3,5-dibromophenyl)methyl]amino]-, trans-;n-(2-amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol;n-(2-amino-3,4-dibromocyclohexyl)-trans-4-aminocyclohexanol;N-(trans-4-Hidroxiciclohexil)-(2-amino-3,5-dibromobencil)amina;N-(trans-4-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine
CAS:18683-91-5
MF:C13H18Br2N2O
MW:378.1
EINECS:242-500-3
Product Categories:API
Mol File:18683-91-5.mol
Ambroxol Structure
Ambroxol Chemical Properties
Melting point 233-234 C
Boiling point 468.6±45.0 °C(Predicted)
density 1.5863 (rough estimate)
refractive index 1.6220 (estimate)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility Soluble in Water.
form solid
pka15.12±0.40(Predicted)
color White
Stability:Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
CAS DataBase Reference18683-91-5(CAS DataBase Reference)
NIST Chemistry ReferenceAmbroxol(18683-91-5)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 36-26
WGK Germany 3
RTECS GV8423000
Toxicityguinea pig,LD50,intraperitoneal,280mg/kg (280mg/kg),Medicamentos de Actualidad. Vol. 15, Pg. 523, 1979.
MSDS Information
Ambroxol Usage And Synthesis
DescriptionAmbroxol HCl (18683-91-5) is a radical scavenger with anti-inflammatory activity. Blocks the generation of reactive oxygen species by bronchoalveolar lavage cells, inhibits doxorubicin-induced lipid peroxidation (70 mg/kg in rat), and inhibits the release of inflammatory mediators from human leukocytes and mast cells (effective dose ~ 100 μM)
OriginatorMucosolvan,Thomae,W. Germany,1980
Usesexpectorant
UsesAmbroxol is a metabolite of Bromohexine. Ambroxol Hydrochloride is a bronchosecretolytic drug. Free base of Ambroxol Hydrochloride (A575900).
DefinitionChEBI: Ambroxol is an aromatic amine.
Manufacturing Process6.5 g of N-(trans-p-hydroxycyclohexyl)-(2-aminobenzyl)-amine were dissolved in a mixture of 80 cc of glacial acetic acid and 20 cc of water, and then 9.6 g of bromine were added dropwise at room temperature while stirring the solution. After all of the bromine had been added, the reaction mixture was stirred for two hours more and was then concentrated in a water aspirator vacuum. The residue was taken up in 2 N ammonia, the solution was extracted several times with chloroform, and the organic extract solutions were combined and evaporated. The residue, raw N-(trans-phydroxycyclohexyl)-( 2-amino-3,5-dibromobenzyl)-amine, was purified with chloroform and ethyl acetate over silica gel in a chromatographic column, the purified product was dissolved in a mixture of ethanol and ether, and the solution was acidified with concentrated hydrochloric acid. The precipitate formed thereby was collected and recrystallized from ethanol and ether, yielding N-(trans-p-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine hydrochloride, MP 233-234.5°C (decomposition).
Therapeutic FunctionExpectorant
References1) Teramoto et al. (1999), Effects of ambroxol on spontaneous or stimulated generation of reactive oxygen species by bronchoalveolar lavage cells harvested from patients with or without chronic obstructive pulmonary diseases; Pharmacology, 59 135 2) Nowak et al. (1995), Ambroxol inhibits doxorubicin-induced lipid peroxidation in heart of mice; Free Radic. Biol. Med., 19 659 3) Gibbs et al. (1999), Ambroxol inhibits the release of histamine, leukotrienes and cytokines from human leukocytes and mast cells; Inflamm. Res., 48 86
AMBROXOL HCL AMBROXOL HYDROCHLORIDE IMP. A (EP) 2-AMINO-3,5-DIBROMOPHENYL)METHANOL AMBROXOL HYDROCHLORIDE IMP. C (EP):TRANS-4-[[(E)2-AMINO-3,5-DIBROMOBENZYLIDEN]AMINO]CYCLOHEXANOL Trimethoprim RAC TRANS AMBROXOL-D5 ALTRENOGEST Ambroxol HCL EP2002 Neltenexine 4-Hydroxybenzylamine 6-Aminocaproic acid Glycine 4-Fluorobenzylamine trans,trans-2,4-Undecadienal Phenoxybenzamine hydrochloride Cyclamic acid AMINO ACIDS Molasses Ambroxol

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