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| CAS No.: | 23828-92-4 |
|---|---|
| Name: | Ambroxol hydrochloride |
| Molecular Structure: | |
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|
|
| Formula: | C13H19Br2ClN2O |
| Molecular Weight: | 414.568 |
| Synonyms: | Hustless (TN);trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride;(2-amino-3,5-dibromo-phenyl)methyl-(4-hydroxycyclohexyl)azanium;18683-91-5;Ambroxol lozenge;Ambroxol Hcl;Altretamine;Mucoangin;Hustless;Mucolear; |
| EINECS: | 245-899-2 |
| Density: | 1.612 g/cm3 |
| Melting Point: | 233-234.5 °C |
| Boiling Point: | 468.6 °C at 760 mmHg |
| Flash Point: | 237.2 °C |
| Solubility: | Slightly soluble in water (~5 mg/ml) or ethanol (~5 mg/ml). |
| Appearance: | white crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 36 |
| PSA: | 58.28000 |
| LogP: | 4.96100 |
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- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol for 1h; pH=Ca. 1; Concentration; | 97% |
| With hydrogenchloride In water; acetone at 0℃; for 1h; Solvent; Temperature; | 97% |
- 27489-62-9
trans-4-hydroxycyclohexylamine
- 50910-55-9
3,5-dibromo-2-amino benzaldehyde
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: trans-4-hydroxycyclohexylamine; 3,5-dibromo-2-amino benzaldehyde With lithium perchlorate; sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1.5h; Stage #2: With hydrogenchloride In water; acetone at 20℃; for 1h; Solvent; | 96.26% |
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol With methanol; formic acid; 5%-palladium/activated carbon at 40℃; for 5h; Inert atmosphere; Green chemistry; Stage #2: With hydrogenchloride In ethanol; water at 20℃; for 2.5h; Reagent/catalyst; Solvent; Green chemistry; | 95% |
| Stage #1: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol With sodium tetrahydroborate In ethylene glycol at 20℃; for 7h; Stage #2: With hydrogenchloride In ethylene glycol; acetone at 20℃; for 2h; | |
| Stage #1: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol With sodium tetrahydroborate In ethanol at 25℃; Stage #2: With hydrogenchloride In 1,4-dioxane at 25℃; | n/a |
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Stage #1: trans-4-[(2-amino-3,5-dibromobenzoyl)amino]cyclohexanol With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran; water at 65℃; for 24h; Inert atmosphere; Cooling with ice; Stage #2: With hydrogenchloride In water for 2h; Temperature; Solvent; Reflux; | 84% |
- 95-53-4
o-toluidine
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: hydrogenchloride / water / 0.5 h / 0 - 20 °C 1.2: 30 - 90 °C 1.3: pH 7 2.1: sodium carbonate / N,N-dimethyl-formamide / 90 - 110 °C 3.1: hydrogenchloride / methanol / 1 h / pH Ca. 1 View Scheme |
- 861787-48-6
3,5-dibromo-2-nitro-benzaldehyde
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: toluene / 3 h / Reflux 2: palladium on activated charcoal; hydrogen / methanol / 10 h / 70 °C / Autoclave 3: hydrogenchloride / acetone; water / 1 h / 0 °C View Scheme |
- 552-89-6
2-nitro-benzaldehyde
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: bromine / methanol / 3 h / 50 °C 2: toluene / 3 h / Reflux 3: palladium on activated charcoal; hydrogen / methanol / 10 h / 70 °C / Autoclave 4: hydrogenchloride / acetone; water / 1 h / 0 °C View Scheme | |
| Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / toluene / 1.5 h / Reflux 2.1: hydrazine hydrate / tetrahydrofuran / 1.5 h / 50 - 55 °C / Inert atmosphere 3.1: bromine; dihydrogen peroxide / dichloromethane; water 4.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C 5.1: lithium perchlorate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 20 °C 5.2: 1 h / 20 °C View Scheme |
- 26908-34-9
N-(2-(1,3-dioxolan-2-yl))phenylamine
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: bromine; dihydrogen peroxide / dichloromethane; water 2.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C 3.1: lithium perchlorate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 20 °C 3.2: 1 h / 20 °C View Scheme |
- 48140-35-8
2-(2-nitrophenyl)-1,3-dioxolane
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1.1: hydrazine hydrate / tetrahydrofuran / 1.5 h / 50 - 55 °C / Inert atmosphere 2.1: bromine; dihydrogen peroxide / dichloromethane; water 3.1: toluene-4-sulfonic acid / acetone / 1 h / 20 °C 4.1: lithium perchlorate; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 1.5 h / 20 °C 4.2: 1 h / 20 °C View Scheme |
- 54840-15-2
4-N-tert-butoxycarbonylaminophenol
- 23828-92-4
ambroxol hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1.1: hydrogen; [Rh(cod)(CI)(CAACCy)] / n-heptane / 48 h / 40 °C 2.1: ethanol / 90 °C 3.1: sodium tetrahydroborate / ethanol / 25 °C 3.2: 25 °C View Scheme |
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Chemistry
Molecular Structure:
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Molecular Formula: C13H19Br2ClN2O
Molecular Weight: 414.5638
IUPAC Name: 4-[(2-Amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol hydrochloride
Synonyms of Ambroxol hydrochloride (CAS NO.23828-92-4): Ambroxol lozenge ; CCRIS 8686 ; EINECS 245-899-2 ; Mucoangin ; Mucolear ; Mucosolvan ; NA 872 hydrochloride ; UNII-CC995ZMV90 ; trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride ; Cyclohexanol, 4-(((2-amino-3,5-dibromophenyl)methyl)amino)-, monohydrochloride, trans- (9CI) ; Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)-, hydrochloride, trans- (8CI) ; Cyclohexanol, 4-(N-(2-amino-3,5-dibromobenzyl)amino)-, hydrochloride (E)-
CAS NO: 23828-92-4
Classification Code: Drug / Therapeutic Agent ; Reproductive Effect
Melting Point: 233-234.5°C
H bond acceptors: 3
H bond donors: 4
Freely Rotating Bonds: 5
Polar Surface Area: 58.28 Å2
Flash Point: 251.7 °C
Enthalpy of Vaporization: 79.99 kJ/mol
Boiling Point: 492.6 °C at 760 mmHg
Vapour Pressure: 1.61E-10 mmHg at 25°C
Uses
Ambroxol hydrochloride (CAS NO.23828-92-4) is used as antitussive and expectorant agent.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | intraperitoneal | 125mg/kg (125mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| dog | LD50 | oral | 500mg/kg (500mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| guinea pig | LD50 | intraperitoneal | 280mg/kg (280mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| guinea pig | LD50 | oral | 1180mg/kg (1180mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| mouse | LD50 | intraperitoneal | 268mg/kg (268mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| mouse | LD50 | intravenous | 138mg/kg (138mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| mouse | LD50 | oral | 2380mg/kg (2380mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981. |
| mouse | LD50 | subcutaneous | 1060mg/kg (1060mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 263, 1981. |
| rabbit | LD50 | intravenous | 64mg/kg (64mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: ATAXIA | Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981. |
| rabbit | LD50 | oral | 2597mg/kg (2597mg/kg) | GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM | Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981. |
| rabbit | LDLo | intraperitoneal | 400mg/kg (400mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 889, 1978. | |
| rat | LD50 | intraperitoneal | 262mg/kg (262mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: PERITONITIS | Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981. |
| rat | LD50 | intravenous | 100mg/kg (100mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Oyo Yakuri. Pharmacometrics. Vol. 21, Pg. 281, 1981. |
| rat | LD50 | oral | 4203mg/kg (4203mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 263, 1981. |
| rat | LD50 | subcutaneous | 1489mg/kg (1489mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 263, 1981. |
Safety Profile
Safety Information of Ambroxol hydrochloride (CAS NO.23828-92-4):
Hazard Codes:Xn 
Risk Statements:22
22:Harmful if swallowed
Safety Statements:36
36:Wear suitable protective clothing
WGK Germany:3
RTECS:GV8423000
Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of Br−, NOx, and HCl.
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