4-Aminopyridine

Base Information

• Chemical Name: 4-Aminopyridine
• CAS No.: 504-24-5
• Molecular Formula: C5H6N2
• Molecular Weight: 94.116
• Hs Code.: 2933.39
• European Community (EC) Number: 207-987-9,635-582-0
• NSC Number: 757845,15041
• UN Number: 2671
• UNII: BH3B64OKL9
• DSSTox Substance ID: DTXSID0023870
• Nikkaji Number: J1.568G,J270.956B
• Wikipedia: 4-Aminopyridine
• Wikidata: Q372539
• NCI Thesaurus Code: C76777
• RXCUI: 897018
• Pharos Ligand ID: M5RAU2PYY1GR
• Metabolomics Workbench ID: 54974
• ChEMBL ID: CHEMBL284348
• Mol file: 504-24-5.mol

Synonyms:4 Aminopyridine;4 Aminopyridine Sustained Release;4-Aminopyridine;4-Aminopyridine Sustained Release;Dalfampridine;Fampridine SR;Fampridine-SR;Pymadine;Sustained Release, 4-Aminopyridine;VMI 103;VMI-103;VMI103

Chemical Property of 4-Aminopyridine

Chemical Property:

• Appearance/Colour: white to slightly yellow fine crystalline powder
• Vapor Pressure: 0.0165mmHg at 25°C
• Melting Point: 157 °C
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 255.2 °C at 760 mmHg
• PKA: 9.114(at 25℃)
• Flash Point: 131.8 °C
• PSA: 38.91000
• Density: 1.107 g/cm³
• LogP: 1.24500
• Storage Temp.: 0-6°C
• Solubility.: H2O: soluble50mg/mL, clear, colorless
• 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. So
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 94.053098200
• Heavy Atom Count: 7
• Complexity: 48
• Transport DOT Label: Poison

Purity/Quality:

99.9% ^*data from raw suppliers

4-Aminopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N,Xi
• Hazard Codes: T+,N,T,Xi
• Statements: 28-36/37/38-51/53-23/24/25
• Safety Statements: 26-36/37/39-45-60-61-37/39-28A-1

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Avicides
• Drug Classes: Multiple Sclerosis Agents
• Canonical SMILES: C1=CN=CC=C1N
• Recent ClinicalTrials: Effect of Dalfampridine in Patients With Hereditary Spastic Paraplegia
• Recent EU Clinical Trials: Clemastine fumarate as remyelinating treatment in internuclear ophthalmoparesis and multiple sclerosis
• Description: 4-Aminopyridine (4-AP, fampridine, dalfampridine) 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.
• Uses: Avitrol (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. Dalfampridine 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.

Technology Process of 4-Aminopyridine

There total 99 articles about 4-Aminopyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-nitropyridine (1122-61-8) → 4-aminopyridine (504-24-5)

Guidance literature:

With C₃₆H₅₆Cl₃CrN₂O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 60 ℃; for 24h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.0c12318

Reference yield: 97.0%

N-(4-pyridyl) t-butyl carbamate (98400-69-2) → 4-aminopyridine (504-24-5)

Guidance literature:

With nitric acid; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(01)00900-0

Reference yield: 97.0%

4-iodopyridine (15854-87-2) → 4-aminopyridine (504-24-5)

Guidance literature:

With copper(l) iodide; ascorbic acid; In ammonia; at 25 ℃; for 18h; liquid NH₃;

DOI:10.1021/jo301204t

upstream raw materials:

pyridine

4-Chloropyridine

4-aminopyridine-1-oxide

triphenyl phosphite

Downstream raw materials:

1,3-bis(pyridin-4-yl)urea

N-(pyridin-4-yl)pyridine-3-carboxamide

4-(Methylamino)pyridine

dmap

Refernces

• 1、 Boer,den Hertog. "-". . p. 1943. Retrieved 1969.
• 2、 Liu, Xin,Werner, Thomas. "Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes". . p. 10590 - 10597. Retrieved 2021/08/20.
• 3、 Argüello, Juan E.,Lanterna, Anabel E.,Lemir, Ignacio D.,Scaiano, Juan C.. "Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths". supporting information. p. 10239 - 10242. Retrieved 2020/10/02.