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| CAS No.: | 101-26-8 |
|---|---|
| Name: | Mestinon |
| Molecular Structure: | |
|
|
|
| Formula: | C9H13BrN2O2 |
| Molecular Weight: | 261.118 |
| Synonyms: | Pyridinium, 3-hydroxy-1-methyl-, bromide, dimethylcarbamate(8CI);Carbamic acid, dimethyl-, ester with 3-hydroxy-1-methylpyridiniumbromide (8CI);1-Methyl-3-hydroxypyridinium bromide dimethylcarbamate;3-(Dimethylcarbamoyloxy)-1-methylpyridinium bromide;3-(Dimethylcarbamyloxy)-1-methylpyridinium bromide;3-[[(Dimethylamino)carbonyl]oxy]-1-methylpyridinium bromide;Kalimin;Kalymin;3-Hydroxy-1-methylpyridiniumbromide, dimethylcarbamate (6CI,7CI);Pyridinium, 3-[[(dimethylamino)carbonyl]oxy]-1-methyl-,bromide (9CI); |
| EINECS: | 202-929-9 |
| Density: | 0.9613 g/cm3 (20oC) |
| Melting Point: | 154 °C |
| Boiling Point: | 88 (25 torr) |
| Solubility: | soluble in ethanol and water |
| Appearance: | Pale yellow to colorless liquid |
| Hazard Symbols: |
 T+
|
| Risk Codes: | 26/27/28-43 |
| Safety: | 22-36/37/39-45 |
| PSA: | 33.42000 |
| LogP: | -2.42450 |
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| Conditions | Yield |
|---|---|
| In acetone for 48h; Ambient temperature; | 89% |
| With benzene | |
| With toluene | |
| With acetone | |
| With acetone |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 47 percent / Et3N / toluene / 4 h / Heating 2: 89 percent / acetone / 48 h / Ambient temperature View Scheme | |
| Multi-step reaction with 2 steps 1: triethylamine; benzene 2: toluene View Scheme | |
| Multi-step reaction with 2 steps 1: chloroform / Behandeln des Reaktionsprodukts mit wss.Dimethylamin-Loesung 2: acetone View Scheme | |
| Multi-step reaction with 2 steps 1: xylene 2: acetone View Scheme |
- 101-26-8
pyridostigmine bromide
A
- 3554-74-3
1-methyl-3-hydroxypiperidine
B
- 5519-50-6
1-methyl-3-piperidone
E
- 6659-30-9
3-dimethylcarbamoyloxy-1-methyl-piperidine
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate Product distribution; different pH, temperature, time and solvents; |
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate In water for 15h; Ambient temperature; | |
| With sodium tetrahydroborate In water for 0.25h; Ambient temperature; |
- 101-26-8
pyridostigmine bromide
| Conditions | Yield |
|---|---|
| In aq. phosphate buffer pH=7.4; UV-irradiation; |
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Chemistry
IUPAC Name: (1-Methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate bromide
Molecular Formula: C9H13BrN2O2
Molecular Weight: 261.12
Molecular Structure: .jpg)
EINECS: 202-929-9
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 33.42 Å2
Melting Point: 154 °C
Appearance: Pale yellow to colorless liquid
Solubility: soluble in ethanol and water
Product Categories of Mestinon (CAS NO.101-26-8): Pyridinium Compounds
SMILES: [Br-].O=C(Oc1ccc[n+](c1)C)N(C)C
InChI: InChI=1/C9H13N2O2.BrH/c1-10(2)9(12)13-8-5-4-6-11(3)7-8;/h4-7H,1-3H3;1H/q+1;/p-1
InChIKey: VNYBTNPBYXSMOO-REWHXWOFAR
Std. InChI: InChI=1S/C9H13N2O2.BrH/c1-10(2)9(12)13-8-5-4-6-11(3)7-8;/h4-7H,1-3H3;1H/q+1;/p-1
Std. InChIKey: VNYBTNPBYXSMOO-UHFFFAOYSA-M
Uses
Mestinon (CAS NO.101-26-8) is anti-cholinesterase drugs for myasthenia gravis, post-operative functional flatulence and urinary retention
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| man | TDLo | oral | 9mg/kg (9mg/kg) | PERIPHERAL NERVE AND SENSATION: FASCICULATIONS | Israel Journal of Medical Sciences. Vol. 27, Pg. 659, 1991. |
| mouse | LD50 | intraperitoneal | 1mg/kg (1mg/kg) | Drugs in Japan Vol. 6, Pg. 354, 1982. | |
| mouse | LD50 | intravenous | 1500ug/kg (1.5mg/kg) | Medicinal Chemistry, A Series of Reviews. Vol. 3, Pg. 329, 1956. | |
| mouse | LD50 | oral | 16mg/kg (16mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Gendai no Rinsho. Vol. 2, Pg. 828, 1968. |
| mouse | LD50 | subcutaneous | 1500ug/kg (1.5mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Gendai no Rinsho. Vol. 2, Pg. 828, 1968. |
| rat | LD50 | intramuscular | 2790ug/kg (2.79mg/kg) | Drug and Chemical Toxicology. Vol. 7, Pg. 507, 1984. | |
| rat | LD50 | intraperitoneal | 2699ug/kg (2.699mg/kg) | Fundamental and Applied Toxicology. Vol. 4, Pg. S195, 1984. | |
| rat | LD50 | oral | 37500ug/kg (37.5mg/kg) | Drugs in Japan Vol. -, Pg. 1042, 1995. | |
| rat | LD50 | subcutaneous | 3100ug/kg (3.1mg/kg) | Journal of Medicinal Chemistry. Vol. 26, Pg. 145, 1983. | |
| women | TDLo | oral | 7800ug/kg (7.8mg/kg) | PERIPHERAL NERVE AND SENSATION: FASCICULATIONS SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE GASTROINTESTINAL: NAUSEA OR VOMITING | Israel Journal of Medical Sciences. Vol. 27, Pg. 659, 1991. |
Safety Profile
Safety Information about Mestinon (CAS NO.101-26-8):
Hazard Codes: 
T+
Risk Statements: 26/27/28-43
R26/27/28: Very toxic by inhalation, in contact with skin and if swallowed.
R43: May cause sensitization by skin contact.
Safety Statements: 22-36/37/39-45
S22: Do not breathe dust.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
RTECS: UU5270000
Poison by ingestion, intramuscular, subcutaneous, intravenous and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of Br− and NOx. See also CARBAMATES and ESTERS.
Specification
Mestinon (CAS NO.101-26-8), its Synonyms are Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-, bromide ; Pyridinium, 3-hydroxy-1-methyl-, bromide, dimethylcarbamate (ester) ; Pyridostigmine bromide ; 1-Methyl-3-hydroxypyridinium bromide dimethylcarbamate ; 3-(((Dimethylamino)carbonyl)oxy)-1-methylpyridinium bromide ; 3-(Dimethylcarbamyloxy)-1-methylpyridinium bromide .