Distigmine Bromide
CAS: 15876-67-2
Category: Pharmaceutical Intermediates
| Purity | Reagent Grade ≥95%, Standard Grade ≥98%, High-Purity Grade ≥99%, Pharmaceutical Grade ≥99.0–101.0% |
| Molecular Formula | C22H32Br2N4O4 |
| Molecular Weight | 576.32 |
| Appearance | White to off-white crystalline powder or solid |
| Packaging | 5 mg/glass vial, 10 mg/glass vial, 25 mg/glass vial, 50 mg/glass vial, 100 mg/glass vial, 250 mg/glass vial, 1 g/glass vial, 5 g/glass vial, 25 g/HDPE bottle, or 1 kg/aluminum foil bag |
| Testing Indicators | Appearance — Visual inspection (white to off-white crystalline powder); Melting point — Capillary method (decomposition at 147–150°C, literature; micro melting point 147–150°C); Purity — HPLC-UV (≥95–99.5%, C18 column, acetonitrile:buffer gradient, λ=220–254 nm); Related substances — HPLC (impurity profiling including pyridostigmine, neostigmine analogs, and carbamate hydrolysis products); Assay — Titrimetric or HPLC (JP XVII: not less than 98.5% and not more than 101.0% of C22H32Br2N4O4, calculated on the dried basis); Loss on drying — Gravimetric (≤0.5%); Residue on ignition — Gravimetric (≤0.1%); Heavy metals — Colorimetric/ICP-MS (≤20 ppm); Bromide content — Argentometric titration (theoretical: 27.73% w/w Br); Identification — FTIR (characteristic peaks: pyridinium C–H ~3100 cm⁻¹, aromatic C=C ~1600 cm⁻¹, carbamate C=O ~1700 cm⁻¹, C–O–C ~1250 cm⁻¹, C–N ~1100 cm⁻¹, N–CH₃ ~1450 cm⁻¹); UV spectrophotometry (λmax ~260 nm, pyridinium chromophore); ¹H NMR (DMSO-d₆: δ 1.30 ppm broad multiplet hexamethylene CH₂, δ 2.90 ppm singlet N(CH₃)₂, δ 3.80 ppm singlet pyridinium N–CH₃, δ 7.20–8.50 ppm multiplet aromatic protons); ¹³C NMR (DMSO-d₆: δ 25–30 ppm hexamethylene CH₂, δ 35 ppm N(CH₃)₂, δ 48 ppm pyridinium N–CH₃, δ 120–150 ppm aromatic carbons, δ 155 ppm carbamate C=O); Mass spectrometry — ESI-MS (m/z 577/579 [M+H]⁺, characteristic bromine isotope pattern 1:1); Water content — Karl Fischer titration (GB/T 6283/EP 2.5.12); pH — Potentiometry (aqueous solution, neutral to slightly acidic); Acute toxicity — LD50 determination (mouse i.v. 300 µg/kg, mouse p.o. 10.5 mg/kg, rat i.v. 740 µg/kg, rat p.o. 10 mg/kg). |
| Storage Notes | Store in a cool, dry, well-ventilated area at 2–8°C. Protect from light, moisture, and air. Keep container tightly sealed. Store powder at -20°C for long-term stability (up to 3 years); at 4°C for 2 years; at room temperature for short-term storage (days to weeks). Hygroscopic and temperature-sensitive material; avoid prolonged exposure to light, heat, and humid conditions. The compound is highly toxic (H300, fatal if swallowed); store in a secure location with restricted access. Store away from strong oxidizing agents, strong bases, and incompatible substances. Use inert atmosphere (nitrogen or argon) for long-term storage if available. |
| Lead Time | 10 days |
Distigmine Bromide (INN, also known as Ubretid, BC-51, or Hexamarium) is a long-acting, reversible carbamate cholinesterase inhibitor and parasympathomimetic agent. It functions as a potent inhibitor of acetylcholinesterase (EC 3.1.1.8) and plasma cholinesterase, binding directly and competitively to the agonist binding sites of muscarinic receptors. Used as a pharmaceutical intermediate and active pharmaceutical ingredient (API) for the development and quality control of tablet and injectable formulations. Approved for clinical use in the treatment of myasthenia gravis, postoperative urinary retention, prevention of ileus and intestinal atony following surgery, underactive neurogenic bladder, and detrusor underactivity. It has a longer duration of action and enhanced drug accumulation compared to pyridostigmine and neostigmine. ATC code: N07AA03. Also employed in analytical method development, forced degradation studies, and pharmacopoeial compliance testing. Caution: High risk of cholinergic crisis due to drug accumulation; mortality rate 3–25% if untreated.