Product Name

  • Name

    3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium methyl sulfate

  • EINECS 200-109-5
  • CAS No. 51-60-5
  • Article Data8
  • CAS DataBase
  • Density
  • Solubility 1g/10mL in water
  • Melting Point 175-177 °C(lit.)
  • Formula C13H22N2O6S
  • Boiling Point 457oC
  • Molecular Weight 334.393
  • Flash Point
  • Transport Information UN 2811 6.1/PG 2
  • Appearance Crystalline solid
  • Safety 36-45-36/37/39-28A
  • Risk Codes 28-36/37/38-42/43-26/27/28
  • Molecular Structure Molecular Structure of 51-60-5 (3-[[(Dimethylamino)carbonyl]oxy]-N,N,N-trimethylbenzenaminium methyl sulfate)
  • Hazard Symbols VeryT+
  • Synonyms Prostigmin methyl sulfate;Benzenaminium,3-[[(dimethylamino)carbonyl]- oxy]-N,N,N-trimethyl-,methyl sulfate;AR-32;Normastigmin;Polstigmine;Stigmanol methyl sulfate;(3-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamic ester;[3-(Dimethylcarbamoyl)oxyphenyl]trimethylammonium methyl sulfate;Synthostigmine methyl sulfate;[3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; sulfonatooxymethane;Vagostigmin;Philostigmin methyl sulfate;[3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; sulfooxymethane;Dimethylcarbamic ester of 3-oxyphenyltrimethylammonium methylsulfato;Leostigmine methyl sulfate;Synstigmine;Proserine methyl sulfate;Proserine;Neostigmine monomethyl sulfate;[3-(Dimethylcarbamoxy)phenyl]trimethylammonium methyl sulfate;Neostigmine methosulfate;Syntostigmin (injection);SB-23;Prostigmine methyl sulfate;Kirkstigmine;Proserin;Ammonium, [3-(dimethylcarbamoyloxy)phenyl]trimethyl-, methyl sulfate;Prostigmin (TN);neostigmine metilsulfate;
  • PSA 104.35000
  • LogP 2.11750

Synthetic route

norneostigmine
16088-19-0

norneostigmine

dimethyl sulfate
77-78-1

dimethyl sulfate

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
In acetone at 20℃; four neck round bottom flask;85%
In tetrahydrofuran at 20℃; for 8h;70%
With acetone
With acetone
Dimethylcarbaminsaeure-3-aminophenylester
19962-04-0

Dimethylcarbaminsaeure-3-aminophenylester

dimethyl sulfate
77-78-1

dimethyl sulfate

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
With calcium carbonate In acetone at 25 - 30℃; Reagent/catalyst;84.6%
3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: acetone
View Scheme
dimethyl sulfate
77-78-1

dimethyl sulfate

3-Dimethylaminophenol
99-07-0

3-Dimethylaminophenol

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

Conditions
ConditionsYield
Stage #1: 3-Dimethylaminophenol With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 0.0583333h;
Stage #2: N,N-Dimethylcarbamoyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 40℃; for 0.00833333h;
Stage #3: dimethyl sulfate Further stages;
...Expand
neostigmine methyl sulfate
51-60-5

neostigmine methyl sulfate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

(3-((dimethylcarbamoyl)oxy)phenyl)boronic acid

(3-((dimethylcarbamoyl)oxy)phenyl)boronic acid

Conditions
ConditionsYield
Stage #1: neostigmine methyl sulfate; bis(pinacol)diborane With 10H-phenothiazine; caesium carbonate In acetonitrile for 18h; Irradiation; Sealed tube; Inert atmosphere;
Stage #2: With hydrogenchloride; dihydroxy-methyl-borane In acetone
Stage #3: With D-Fructose; sodium carbonate In water		74%

Neostigmine methyl sulfate Chemical Properties

Molecular Structure of Neostigmine methyl sulfate (CAS NO.51-60-5):

IUPAC Name: [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium; methyl sulfate 
Empirical Formula: C13H22N2O6S
Molecular Weight: 334.3886
ACD/LogP: -3.03
of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): -3.03
ACD/LogD (pH 7.4): -3.03
ACD/BCF (pH 5.5): 1
ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 1
ACD/KOC (pH 7.4): 1
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 29.54Å2
EINECS: 200-109-5
Melting point: 175-177 °C(lit.)
Storage temp: ?20°C
Solubility: H2O:1g/mL
Water Solubility: 1g/10mL
Merck: 6464
 InChI
InChI=1/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
Smiles
c1(cc(ccc1)[N+](C)(C)C)OC(N(C)C)=O.S(OC)(=O)(=O)[O-]
Product Categories: Alkaloids;Ammonium Polyhalides, etc. (Quaternary); Quaternary Ammonium Compounds; Intermediates & Fine Chemicals; Pharmaceuticals

Neostigmine methyl sulfate Toxicity Data With Reference

1.    

scu-rat LD50:334 µg/kg

     TXAPA9    Toxicology and Applied Pharmacology. 25 (1973),569.
2.    

orl-mus LD50:7500 µg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 99 (1950),16.
3.    

ipr-mus LD50:230 µg/kg

     ATXKA8    Archiv fuer Toxikologie. 29 (1972),39.
4.    

scu-mus LD50:420 µg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 99 (1950),16.
5.    

ivn-mus LD50:160 µg/kg

     JPETAB    Journal of Pharmacology and Experimental Therapeutics. 99 (1950),16.
6.    

scu-dog LD50:50 µg/kg

     NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB158-508 .
7.    

scu-cat LDLo:50 µg/kg

     NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB158-508 .
8.    

ims-rbt LD50:310 µg/kg

     AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 81 (1950),276.

Neostigmine methyl sulfate Safety Profile

A deadly poison by ingestion, intravenous, subcutaneous, intraperitoneal, and intramuscular routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of SOx, NH3, and NOx. See also Carbamates.
Hazard Codes: T+
Risk Statements: 28-36/37/38-42/43-26/27/28
R36/37/38:Irritating to eyes, respiratory system and skin ;
R42/43:May cause sensitization by inhalation and skin contact ;
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed ;
Safety Statements: 36-45-36/37/39-28
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) ;
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection ;
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: CY1225000
HazardClass: 6.1(a)
PackingGroup: II

Neostigmine methyl sulfate Specification

 Neostigmine methyl sulfate , with CAS number of 51-60-5, can be called (3-(Dimethylcarbamoxy)phenyl)trimethylammonium methyl sulfate ; (m-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamate ; (3-Hydroxyphenyl)trimethylammonium methyl sulfate dimethylcarbamic ester ; 3-(Dimethylcarbamoxy)phenyl trimethylammonium methyl sulfate ; Carbamic acid, dimethyl-, ester with (m-hydroxyphenyl)trimethylammonium methyl sulfate . Neostigmine methyl sulfate (CAS NO.51-60-5) is stable under normal temperatures and pressures.Incompatibilities with other materials strong oxidizing agents.

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