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Basic Information

Molecular Structure:
CAS No.:	23828-92-4
Name:	Ambroxol hydrochloride
Article Data:	10

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

Synthetic route

: 18683-91-5, 36557-04-7, 107814-37-9
ambroxol

: 23828-92-4
ambroxol hydrochloride

Conditions

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

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%

: trans-4-[(2-amino-3,5-dibromobenzylidene)amino]cyclohexanol

: 23828-92-4
ambroxol hydrochloride

Conditions

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

: trans-4-[(2-amino-3,5-dibromobenzoyl)amino]cyclohexanol

: 23828-92-4
ambroxol hydrochloride

Conditions

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

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

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

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

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

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

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

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:

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⁻, NO_x, and HCl.

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