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18683-91-5

18683-91-5 Structure

18683-91-5 Structure
IdentificationMore
[Name]

Ambroxol
[CAS]

18683-91-5
[Synonyms]

2-amino-3,5-dibromo-n-(trans-4-hydroxycyclohexyl)benzylamine
4-(2-AMINO-3,5-DIBROMO-BENZYLAMINO)-CYCLOHEXANOL
AMBROXOL
ambroxol base
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
N-(trans-p-Hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amine
NA-872
trans-4-((2-Amino-3,5-dibromobencil)amino)ciclohexanol
trans-4-((2-amino-3,5-dibromobenzyl)amine)cyclohexanol
trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol
trans-N-[2-Amino-3,5-dibromobenzyl]-4-hydroxycyclohexylamine
4-[[(2-Amino-3,5-dibromophenyl)methyl]amino]cyclohexanol
Bronchopmnt
[EINECS(EC#)]

242-500-3
[Molecular Formula]

C13H18Br2N2O
[MDL Number]

MFCD00242702
[Molecular Weight]

378.1
[MOL File]

18683-91-5.mol
Chemical PropertiesBack Directory
[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. ]

2-8°C
[solubility ]

Soluble in Water.
[form ]

solid
[pka]

15.12±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 Reference]

18683-91-5(CAS DataBase Reference)
[NIST Chemistry Reference]

Ambroxol(18683-91-5)
Safety DataBack Directory
[Hazard Codes ]

Xn,Xi
[Risk Statements ]

R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[RTECS ]

GV8423000
[REACH Registrations]

Active
[Toxicity]

guinea pig,LD50,intraperitoneal,280mg/kg (280mg/kg),Medicamentos de Actualidad. Vol. 15, Pg. 523, 1979.
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Acetic acid-->Sodium sulfate-->Lithium Aluminum Hydride-->1,4-Dioxane-->Methanesulfonyl chloride-->Sulfurous Acid-->Methyl anthranilate-->2-Methoxyethanol-->Bromide-->Tetrachloroethylene-->1,4-Dibromobenzene-->Octanoic hydrazide-->trans-4-Aminocyclohexanol hydrochloride-->Methanesulfonyl hydrazide-->Ambroxol hydrochloride
Hazard InformationBack Directory
[Description]

Ambroxol 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)
[Originator]

Mucosolvan,Thomae,W. Germany,1980
[Uses]

expectorant
[Definition]

ChEBI: Ambroxol is an aromatic amine.
[Manufacturing Process]

6.5 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 Function]

Expectorant
[References]

1) 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
Spectrum DetailBack Directory
[Spectrum Detail]

Ambroxol(18683-91-5)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

18683-91-5(sigmaaldrich)
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