-
Name
Sodium gualenate
- EINECS 228-309-8
- CAS No. 6223-35-4
- Article Data5
- CAS DataBase
- Density
- Solubility
- Melting Point 98°C(lit.)
- Formula C15H17NaO3S
- Boiling Point
- Molecular Weight 300.354
- Flash Point
- Transport Information
- Appearance
- Safety
- Risk Codes
-
Molecular Structure
- Hazard Symbols
- Synonyms 1-Azulenesulfonicacid, 3,8-dimethyl-5-(1-methylethyl)-, sodium salt (9CI);1-Azulenesulfonicacid, 5-isopropyl-3,8-dimethyl-, sodium salt (7CI,8CI);Azulen SN;Azulene SN;Azunol ST;Azupromin;Guaiazulene 3-sulfonate sodium salt;Guaiazulene soluble;Sodium 1,4-dimethyl-7-isopropylazulene-3-sulfonate;Sodium3-methyl-5-isopropyl-8-methylazulenesulfonate;Sodium5-isopropyl-3,8-dimethyl-1-azulenesulfonate;Sodium7-isopropyl-1,4-dimethylazulene-3-sulfonate;Sodium guaiazulene-3-sulfonate;Sodium guaiazulenesulfonate;
- PSA 65.58000
- LogP 4.51650
Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With sulfuric acid; acetic anhydride at 20℃; for 2h; Cooling with ice; | 87.5% |
| Stage #1: 7-isopropyl-1,4-dimethyl-azulene With sulfuric acid; acetic anhydride at 20℃; for 4h; Stage #2: With sodium hydroxide In water | 57% |
| Multi-step reaction with 2 steps 1: sulfuric acid; acetic anhydride / 3 h / 20 °C 2: sodium hydroxide View Scheme | |
| Stage #1: 7-isopropyl-1,4-dimethyl-azulene With sulfuric acid; acetic anhydride at 20℃; for 3h; Stage #2: With sodium hydroxide |
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16915-32-5
5-isopropyl-3,8-dimethyl-azulene-1-sulfonic acid
-
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6223-35-4
Azulon
Conditions
| Conditions | Yield |
|---|---|
| With sodium hydroxide |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: Azulon With pyridine; oxalyl dichloride In dichloromethane Stage #2: piperazine With pyridine; triethylamine | 43% |
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6223-35-4
Azulon
-
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1338350-96-1
N-ethyl-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
-
1338350-97-2
N-cyclohexyl-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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-
6223-35-4
Azulon
-
-
1338350-98-3
N-benzyl-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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1338350-99-4
N-(4-chlorophenyl)-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
-
1338351-00-0
N-(4-aminophenyl)-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 4 h / 0 °C 2: dichloromethane / 12 h 3: trifluoroacetic acid / dichloromethane / 3 h View Scheme |
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6223-35-4
Azulon
-
-
1338351-02-2
N-[4-(benzylideneamino)phenyl]-5-isopropyl-3,8-dimethylazulene-1-sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
-
1338351-03-3
N-[4-(2-hydroxybenzylideneamino)phenyl]-5-isopropyl-3,8-dimethylazulene-1-sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
-
1338351-04-4
N-[4-(2-thienylmethyleneamino)phenyl]-5-isopropyl-3,8-dimethylazulene-1-sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
-
1338351-09-9
N-amino-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine; hydrazine View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; hydrazine hydrate; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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1338351-05-5
N'-(4-methoxybenzylidene)-5-isopropyl-3,8-dimethylazulene-1-sulfonohydrazide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine; hydrazine 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
1338351-06-6
N'-(4-trifluoromethylbenzylidene)-5-isopropyl-3,8-dimethylazulene-1-sulfonohydrazide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine; hydrazine 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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1338351-07-7
N'-(2-hydroxybenzylidene)-5-isopropyl-3,8-dimethylazulene-1-sulfonohydrazide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine; hydrazine 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
1338351-08-8
N'-(2-thienylmethylene)-5-isopropyl-3,8-dimethylazulene-1-sulfonohydrazide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine; hydrazine 3: ethanol / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
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1338350-89-2
N-(3-bromophenyl)-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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1338350-90-5
N-(2,4-dimethoxyphenyl)-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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1338350-91-6
N,5-diisopropyl-3,8-dimethyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: sodium carbonate decahydrate / 2.5 h / 5 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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1338350-92-7
N-(naphthalen-1-yl)-5-isopropyl-3,8-dimethylazulene-1-sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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-
6223-35-4
Azulon
-
-
1338350-93-8
N-isobutyl-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
1338350-94-9
N-propyl-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: sodium carbonate decahydrate / 1.5 h / 5 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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-
6223-35-4
Azulon
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-
1338350-95-0
N-(4-methylphenyl)-3,8-dimethyl-5-isopropyl-1-azulene sulfonamide
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: pyridine; oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.17 h / Cooling with ice 2: pyridine; triethylamine / dichloromethane / 1 h / 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; pyridine; oxalyl dichloride / dichloromethane / Cooling with ice 2: triethylamine; pyridine / dichloromethane / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
69174-69-2
5-isopropyl-3,8-dimethyl-azulene-1-sulfonyl chloride
Conditions
| Conditions | Yield |
|---|---|
| With pyridine; oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 0.166667h; Cooling with ice; | |
| With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.166667h; | |
| With pyridine; oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane Cooling with ice; | |
| With thionyl chloride In dichloromethane at 0℃; for 4h; |
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6223-35-4
Azulon
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-
1436872-40-0
C22H24O3S
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: pyridine / N,N-dimethyl-formamide; dimethyl sulfoxide / 2.5 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
1436872-41-1
C16H18O4S
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: pyridine / N,N-dimethyl-formamide; dimethyl sulfoxide / 1 h / 20 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone; water / 1 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
1436872-42-2
C17H20O4S
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: pyridine / N,N-dimethyl-formamide; dimethyl sulfoxide / 2 h / 20 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone; water / 2 h / 20 °C View Scheme |
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6223-35-4
Azulon
-
-
1436872-43-3
C18H22O4S
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: pyridine / N,N-dimethyl-formamide; dimethyl sulfoxide / 2.5 h / 20 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone; water / 2.5 h / 20 °C View Scheme |
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6223-35-4
Azulon
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-
1436872-44-4
C23H28O5S
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 0.17 h / 0 °C 2: pyridine / N,N-dimethyl-formamide; dimethyl sulfoxide / 2.5 h / 20 °C 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetone; water / 2.5 h / 20 °C 4: ytterbium(III) triflate; acetic anhydride / nitromethane / 18 h / 20 °C View Scheme |
Sodium gualenate Chemical Properties
Molecular Structure:
Molecular Formula: C15H17NaO3S
Molecular Weight: 300.3484
IUPAC Name: Sodium 3,8-dimethyl-5-propan-2-ylazulene-1-sulfonate
Synonyms of Sodium gualenate (CAS NO.6223-35-4): 3,8-Dimethyl-5-(1-methylethyl)-1-azulenesulfonic acid sodium salt ; Azulen SN ; Azulon ; Azupromin ; CCRIS 3781 ; EINECS 228-309-8 ; Guajazulen-3-sulfonsaeure, natriumsalz ; Gualenate de sodium ; Gualenate de sodium [INN-French] ; Gualenato sodico ; Gualenato sodico [INN-Spanish] ; Gualenato sodidico ; Natrii gualenas ; Natrii gualenas [INN-Latin] ; Natrium 7-isopropyl-1,4-dimethyl-3-azulensulfonat ; Sodium 5-isopropyl-3,8-dimethyl-1-azulene sulfonate ; Sodium 7-isopropyl-1,4-dimethylazulene-3-sulfonate ; Sodium guaiazulene-3-sulfonate ; UNII-19WSH095WP ; 1-Azulenesulfonic acid, 3,8-dimethyl-5-(1-methylethyl)-, sodium salt (9CI) ; 1-Azulenesulfonic acid, 5-isopropyl-3,8-dimethyl-, sodium salt ; Azuletil sodium
CAS NO: 6223-35-4
Product Categories: Drug / Therapeutic Agent
Sodium gualenate Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 105mg/kg (105mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Shinryo to Shinyaku. Medical Consultation and New Remedies. Vol. 11, Pg. 2533, 1974. |
| mouse | LD50 | oral | 1540mg/kg (1540mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 615, 1969. | |
| mouse | LD50 | subcutaneous | 145mg/kg (145mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Shinryo to Shinyaku. Medical Consultation and New Remedies. Vol. 11, Pg. 2533, 1974. |
| rat | LD50 | intraperitoneal | 180mg/kg (180mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Shinryo to Shinyaku. Medical Consultation and New Remedies. Vol. 11, Pg. 2533, 1974. |
| rat | LD50 | oral | 6380mg/kg (6380mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 615, 1969. | |
| rat | LD50 | subcutaneous | 520mg/kg (520mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Shinryo to Shinyaku. Medical Consultation and New Remedies. Vol. 11, Pg. 2533, 1974. |
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