ChemicalBook > Product Catalog > Pharmaceutical intermediates > Heterocyclic compound > Pyridine compound > Aminopyridine > 4-Aminopyridine
4-Aminopyridine Chemical Properties
- Melting point:157 °C
- Boiling point:273 °C(lit.)
- Density 1.26
- refractive index 1.5560 (estimate)
- Flash point:156°C
- storage temp. 0-6°C
- solubility H2O: soluble50mg/mL, clear, colorless
- pka9.114(at 25℃)
- form Crystalline Powder, Solid or Crystals
- color White to faint grey to light yellow
- Water Solubility Soluble in water(112 g/L at 20 deg C). Soluble in ethyl ether, benzene. Slightly soluble in ligroin. Very soluble in ethanol. Soluble in methanol, acetone, tetrahydrofuran, isopropanol, acetonitrile, N,N-dimethylformamide, dimethylsulfoxide, and ethanol.
- Merck 14,3933
- BRN 105782
- CAS DataBase Reference504-24-5(CAS DataBase Reference)
- NIST Chemistry Reference4-Pyridinamine(504-24-5)
- EPA Substance Registry System4-Aminopyridine (504-24-5)
- Hazard Codes T+,N,T,Xi
- Risk Statements 28-36/37/38-51/53-23/24/25
- Safety Statements 26-36/37/39-45-60-61-37/39-28A-1
- RIDADR UN 2671 6.1/PG 2
- WGK Germany 3
- RTECS US1750000
- F 8-21
- Autoignition Temperature640 °C
- Hazard Note Toxic/Irritant
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29333999
- Hazardous Substances Data504-24-5(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 21 mg/kg
4-Aminopyridine Usage And Synthesis
- DescriptionDalfampridine (also referred to as 4-AP) is the first drug approved by
the FDA to improve walking in patients with multiple sclerosis (MS).
Dalfampridine is a voltage-gated potassium channel blocker that readily
penetrates the CNS and increases the conduction and duration of action
potential across nerve fibers resulting in enhanced functionality as
observed in the walking speed of MS patients.
From a safety perspective, seizure was the most important adverse event from various dalfampridine clinical trials. Therefore, dalfampridine is contraindicated in patients with a history of seizures. Since dalfampridine is primarily excreted by the kidney as unchanged drug, it is also contraindicated in patients with moderate to severe renal impairment. Assessing the overall benefit–risk profile from various clinical trials, the FDA approved dalfampridine (daily oral dose of 10 mg, b.i.d.) to improve walking in MS patients with existing gait impairment.
- Chemical PropertiesWHITE TO SLIGHTLY YELLOW FINE CRYSTALLINE POWDER
- Chemical Properties4-aminopyridine is a white crystalline solid that contains about 98% active ingredient. It is soluble in water and slightly soluble in benzene and ether. 4-Aminopyridine formulations are classifi ed by the US Environmental Protection Agency (US EPA) as restricted use pesticides (RUPs) and therefore should be purchased and used only by certifi ed and trained workers and applicators. Avitrol is available as grain baits or as a powder concentrate. It is one of the most prominent avicides. It is registered with the EPA for use against red-winged blackbirds, blackbirds in agricultural fi elds, grackles, pigeons, and sparrows around public buildings, and various birds around livestock feeding pens. Avitrol repels birds by poisoning a few members of a fl ock, causing them to become hyperactive.
- Chemical Properties4-Aminopyridine is white to tan or brown crystalline material. Odorless.
- OriginatorRush University Medical Center (United States)
- UsesAvitrol (4-aminopyridine), has repellent–toxicant properties for birds and is classed as a severe poison and irritant. This secondary bird repellent can be used as a broadcast bait, causing uncoordinated flight and distress calls and escape responses in nearby birds.
- UsesDalfampridine is used in characterizing subtypes of potassium channel, and has also been used to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. Dalfampridine is a precursor to the drug Pinacidil.
- DefinitionChEBI: An aromatic amine that is pyridine bearing a single amino substituent at position 4. An orphan drug in the US, it is used to improve walking in adults with multiple sclerosis.
- brand nameNeurelan (E′lan);Ampyra.
- General DescriptionWhite crystalline material with no odor. Used as an avicide, an intermediate and as a fixer for some textile dyes.
- Reactivity Profile4-Aminopyridine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
- Health HazardMaterial may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Material affects neural transmission. In sufficient concentrations, material may cause metabolic acidosis, respiratory arrest, and cardiac arrhythmias.
- Health Hazard4-Aminopyridine, a pyridine compound, is an extremely effective bird poison. In agriculture, 4-AP is used as an extremely effective bird poison sold under the brand name Avitrol. It is highly toxic to all mammals including humans if dosages are exceeded, and as an experimental drug, the recommended dose data is unavailable. 4-Aminopyridine blocks
- Fire HazardMaterial may produce irritating or poisonous gases in fire. Runoff from fire control water may give off irritating or poisonous gases.
- Safety ProfilePoison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects by ingestion: hallucinations and vomiting. When heated to decomposition it emits toxic fumes of NOx,.
- Potential ExposureUsed as a chemical intermediate in pharmaceuticals; as an agricultural chemical for field crops; and as a bird repellent and poison
- ShippingUN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
- Purification MethodsCrystallise the aminopyridine from *benzene/EtOH, then recrystallise it twice from water, then crush and dry it for 4hours at 105o [Bates & Hetzer J Res Nat Bur Stand 64A 427 1960]. It has also been crystallised from EtOH, *benzene, *benzene/pet ether, toluene and sublimes in a vacuum. [Beilstein 22/9 V 106.]
- IncompatibilitiesSodium nitrite, strong oxidizers. Avoid contact with acid anhydrides, acid chlorides; and strong acids.
- Waste DisposalConsult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposalIncineration with nitrogen oxides removal from effluent gas.
4-Aminopyridine Preparation Products And Raw materials
- Preparation Products4-ACETAMIDO-3-AMINOPYRIDINE(3-BROMO-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER2,2-DIMETHYL-N-PYRIDIN-4-YL-PROPIONAMIDE4-(Boc-amino)pyridine3-PYRIDINEACETIC ACID, 4-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-A-OXO-, ETHYL ESTERTERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATEefficient polymer catalyst for acrylation-synthesis and characterigation of polyamide containing supernucleophilic reagent4-Iodopyridine2-chloro-5-ethylaminomethylpyridine
- Raw materialsPotassium carbonatePathalic acidPyridine-N-oxide4-Nitropyridine
- 4-Amino-3,5-dichloro-2,6-difluoropyridine 4-AMINO-3-CHLORO-2,5,6-TRIFLUOROPYRIDINE 4-Aminopyridine 4-Amino-2-methoxypyridine Tris Base 4-AMINOPYRIDINE 3-Aminopyridine EC 126.96.36.199 Pyridine Glycine 4-Amino-2-chloropyridine AMINO ACIDS 6-Aminocaproic acid ALTRENOGEST 2-Aminopyridine 4-Amino-3-chloropyridine 4-Amino-3-bromopyridine 4-Aminobutyric acid
- Company Name:Hangzhou Cyanochem Co., Ltd. Gold
- Company Name:Shijiazhuang Sdyano Fine Chemical Co., Ltd. Gold
- Company Name:J & K SCIENTIFIC LTD.
- Tel:400-666-7788 010-82848833-
- Company Name:3B Pharmachem (Wuhan) International Co.,Ltd.
- Tel:18930552037 821-50328103-801
- Company Name:Alfa Aesar