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Mestinon

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Name

Mestinon

EINECS 202-929-9
CAS No. 101-26-8 Density 0.9613 g/cm3 (20oC)
PSA 33.42000 LogP -2.42450
Solubility soluble in ethanol and water Melting Point 154 °C
Formula C9H13BrN2O2 Boiling Point 88 (25 torr)
Molecular Weight 261.118 Flash Point N/A
Transport Information N/A Appearance Pale yellow to colorless liquid
Safety 22-36/37/39-45 Risk Codes 26/27/28-43
Molecular Structure Molecular Structure of 101-26-8 (Mestinon) Hazard Symbols VeryT+
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);

 

Mestinon Synthetic route

74-83-9

methyl bromide

51581-32-9

3-(N,N-Dimethylcarbamoyl)-oxipyridin

101-26-8

pyridostigmine bromide

Conditions
ConditionsYield
In acetone for 48h; Ambient temperature;89%
With benzene
With toluene
With acetone
With acetone
109-00-2

3-HYDROXYPYRIDINE

101-26-8

pyridostigmine bromide

Conditions
ConditionsYield
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

C

Dimethyl-carbamic acid 1-methyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

D

3-<(N,N-dimethyl)-carbamoyl>-1-methyl-1,2,5,6-tetrahydropyridine

E

6659-30-9

3-dimethylcarbamoyloxy-1-methyl-piperidine

Conditions
ConditionsYield
With sodium tetrahydroborate Product distribution; different pH, temperature, time and solvents;
101-26-8

pyridostigmine bromide

A

Dimethyl-carbamic acid 1-methyl-1,2,3,6-tetrahydro-pyridin-3-yl ester

B

3-<(N,N-dimethyl)-carbamoyl>-1-methyl-1,2,5,6-tetrahydropyridine

C

6659-30-9

3-dimethylcarbamoyloxy-1-methyl-piperidine

Conditions
ConditionsYield
With sodium tetrahydroborate In water for 15h; Ambient temperature;
With sodium tetrahydroborate In water for 0.25h; Ambient temperature;

C62H68N16O24S4(4-)*4Na(1+)

101-26-8

pyridostigmine bromide

C9H13N2O2(1+)*Br(1-)*C62H68N16O24S4(4-)*4Na(1+)

Conditions
ConditionsYield
In aq. phosphate buffer pH=7.4; UV-irradiation;

Mestinon Chemical Properties

IUPAC Name: (1-Methylpyridin-1-ium-3-yl) N,N-dimethylcarbamate bromide
Molecular Formula: C9H13BrN2O2
Molecular Weight: 261.12
Molecular Structure:
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

Mestinon Uses

 Mestinon (CAS NO.101-26-8) is anti-cholinesterase drugs for myasthenia gravis, post-operative functional flatulence and urinary retention

Mestinon 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.

Mestinon Safety Profile

Safety Information about Mestinon (CAS NO.101-26-8):
Hazard Codes: VeryT+
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.

Mestinon 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 .

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