Product Name

  • Name

    Mestinon

  • EINECS 202-929-9
  • CAS No. 101-26-8
  • Density 0.9613 g/cm3 (20oC)
  • Solubility soluble in ethanol and water
  • Melting Point 154 °C
  • Formula C9H13BrN2O2
  • Boiling Point 88 (25 torr)
  • Molecular Weight 261.118
  • Flash Point
  • Transport Information
  • 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);
  • PSA 33.42000
  • LogP -2.42450

Synthetic route

methyl bromide
74-83-9

methyl bromide

3-(N,N-Dimethylcarbamoyl)-oxipyridin
51581-32-9

3-(N,N-Dimethylcarbamoyl)-oxipyridin

pyridostigmine bromide
101-26-8

pyridostigmine bromide

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

3-HYDROXYPYRIDINE

pyridostigmine bromide
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
pyridostigmine bromide
101-26-8

pyridostigmine bromide

A

1-methyl-3-hydroxypiperidine
3554-74-3

1-methyl-3-hydroxypiperidine

B

1-methyl-3-piperidone
5519-50-6

1-methyl-3-piperidone

C

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

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

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

E

3-dimethylcarbamoyloxy-1-methyl-piperidine
6659-30-9

3-dimethylcarbamoyloxy-1-methyl-piperidine

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

pyridostigmine bromide

A

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

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

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

C

3-dimethylcarbamoyloxy-1-methyl-piperidine
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;
...Expand
C62H68N16O24S4(4-)*4Na(1+)

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

pyridostigmine bromide
101-26-8

pyridostigmine bromide

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

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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