3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium bromide

• ChemBase ID: 72763
• Molecular Formular: C9H13BrN2O2
• Molecular Mass: 261.11572
• Monoisotopic Mass: 260.01603967
• SMILES: c1c(ccc[n+]1C)OC(=O)N(C)C.[Br-]
• Canonical SMILES: C[n+]1cccc(c1)OC(=O)N(C)C.[Br-]
• 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
• InChIKey: VNYBTNPBYXSMOO-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium bromide
• IUPAC Traditional name: pyridostigmine bromide
• Synonyms: 3-(Dimethylaminocarbonyloxy)-1-methylpyridinium bromide; Pyridostigmine bromide; 3-[[(Dimethylamino)carbonyl]oxy]-1-methyl-pyridinium Bromide; 3-Hydroxy-1-methylpyridinium Bromide Dimethylcarbamate; 1-Methyl-3-hydroxypyridinium Bromide Dimethylcarbamate; 3-[[(Dimethylamino)carbonyl]oxy]-1-methylpyridinium Bromide; Kalimin; Kalymin; Mestinon Bromide; NSC 679759; Piridostigmin; 3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium bromide; Mestinon; Regonol; Pyridostigmine Bromide; 3-Dimethylaminocarbonyloxy-N-methylpyridinium bromide

Database IDs

• CAS Number: 101-26-8
• EC Number: 202-929-9
• MDL Number: MFCD00079283
• PubChem SID: 24277865; 162037684
• PubChem CID: 7550

CALCULATED PROPERTIES

• Acid pKa: 19.526827
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -3.4667275
• LogD (pH = 7.4): -3.4667275
• Log P: -3.4667275
• Molar Refractivity: 49.659 cm^3
• Polarizability: 18.862652 Å^3
• Polar Surface Area: 33.42 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 149-151°C; 154 - 156°C; 154-157°C
• Hydrophobicity(logP): -4.514

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: UU5270000
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 26/27/28-43; R:25
• Safety Statements: 22-36/37/39-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H317-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... ACHE(43)

Product Information

• Purity: 95%
• Salt Data: Bromide

DETAILS

MP Biomedicals - 02193422

(3-Dimethylaminocarbonyloxy-N-methylpyridinium bromide)

Selleck Chemicals - S1608

Research Area: Neurological Disease
Biological Activity:
Pyridostigmine Bromide(Mestinon) is a parasympathomimetic and a reversible cholinesterase inhibitor. Pyridostigmine Bromide inhibits acetylcholinesterase in the synaptic cleft, thus slowing down the hydrolysis of acetylcholine. It is a quaternary carbamate inhibitor of cholinesterase that does not cross the blood-brain barrier, and it is taken daily in anticipation of an attack, which carbamylates about 30% of peripheral cholinesterase enzyme. The carbamylated enzyme eventually regenerates by natural hydrolysis and excess ACh levels revert to normal. [1]

Sigma Aldrich - P9797

Biochem/physiol Actions
Acetylcholinesterase inhibitor.

Toronto Research Chemicals - P991705

Cholinergic, used in the treatment of myasthenia gravis, and is a pre-exposure antidote to chemical warfare agents.

REFERENCES

• http://en.wikipedia.org/wiki/Pyridostigmine
• Kayihan, G., et al.: Toxicol. Environ. Chem., 92, 1783 (2010)
• Yu, Q., et al.: Bioorg. Med. Chem., 18, 4687 (2010)
• Voicu, V., et al.: J. Pharm. Biomed. Anal., 52, 508 (2010)