3,4-Diaminopyridine

Base Information

• Chemical Name: 3,4-Diaminopyridine
• CAS No.: 54-96-6
• Molecular Formula: C5H7N3
• Molecular Weight: 109.131
• Hs Code.: 29333999
• European Community (EC) Number: 200-220-9
• NSC Number: 521760
• UNII: RU4S6E2G0J
• DSSTox Substance ID: DTXSID6046715
• Nikkaji Number: J51.295H
• Wikipedia: Amifampridine,3,4-diaminopyridine
• Wikidata: Q411707
• NCI Thesaurus Code: C82687
• RXCUI: 2106338
• Pharos Ligand ID: TKD5AFJ1327V
• Metabolomics Workbench ID: 152762
• ChEMBL ID: CHEMBL354077
• Mol file: 54-96-6.mol

Synonyms:3,4 Diaminopyridine;3,4-diaminopyridine;amifampridine;amifampridine phosphate;Firdapse;Ruzurgi

Chemical Property of 3,4-Diaminopyridine

Chemical Property:

• Appearance/Colour: brownish to brown-grey crystalline powder
• Vapor Pressure: 1.2E-05mmHg at 25°C
• Melting Point: 216-218 °C(lit.)
• Refractive Index: 480 C
• Boiling Point: 369.3 °C at 760 mmHg
• PKA: 9.17±0.12(Predicted)
• Flash Point: 204.9 °C
• PSA: 64.93000
• Density: 1.251 g/cm³
• LogP: 1.40840
• Storage Temp.: Store below +30°C.
• Solubility.: 30g/l
• Water Solubility.: 24 g/L (20 ºC)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 109.063997236
• Heavy Atom Count: 8
• Complexity: 74.1

Purity/Quality:

99.9% ^*data from raw suppliers

3,4-Diaminopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,T,Xi
• Hazard Codes: T+,T,Xi
• Statements: 25-26-36/37/38
• Safety Statements: 26-28-36/37/39-45-37/39-28A-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Myasthenia Agents
• Canonical SMILES: C1=CN=CC(=C1N)N
• Recent ClinicalTrials: Treatment Use of 3,4 Diaminopyridine in Congenital Myasthenia
• Recent EU Clinical Trials: Improving symptomatic treatment with pyridostigmine and amifampridine: a randomized double-blinded,
• Description: 3,4-diaminopyridine (3,4-DAP, amifampridine) is the leading treatment for Lambert–Eaton myasthenic syndrome (LEMS), an autoimmune disorder with impaired neuromuscular transmission, for which few effective medications are currently available. 3,4-DAP has been available as a therapy for LEMS in special treatment programmes for approximately 25 years.
• Uses: Amifampridine (3,4-Diaminopyridine) is a drug, predominantly in the treatment of a number of rare muscle diseases. 3,4-Diaminopyridine (3,4-DAP) is used in the treatment of Lambert-Eaton myasthenic syndrome (LEMS) and some congenital myasthenic syndromes (CMS). It is used to improve muscle strength. It is a potassium channel blocker in nerve terminals. It inhibits potassium channel efflux, increasing the duration of the action potential, which results in an increase in the duration of calcium channel opening and enhanced acetylcholine (ACh) release. Increased ACh availability at the motor end plate allows muscles to contract.
• Indications: 3,4-diaminopyridine has been used to treat Lambert Eaton myasthenia (LEM) for thirty years despite the lack of conclusive evidence of efficacy. Lambert–Eaton myasthenic syndrome is characterized by muscle weakness, hyporeflexia, and autonomic dysfunction, which result from impaired release of acetylcholine from cholinergic nerve terminals. It is frequently associated with cancer, it is autoimmune-mediated, and treatment has been unsatisfactory. The drug 3,4-diaminopyridine (3,4-DAP) increases neurotransmitter release and also the action potential (by blocking potassium conductance); these actions lead to a nonspecific excitatory effect on the cholinergic system, and provide benefit. It should be taken orally, 4-5 times per day. Adverse effects due to CNS excitation (insomnia, seizures) can occur.

Technology Process of 3,4-Diaminopyridine

There total 11 articles about 3,4-Diaminopyridine 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: 98.0%

4-amino-3-nitropyridine (1681-37-4) → 3,4-diaminopyridine (54-96-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 20h; under 5250.42 Torr;

DOI:10.1002/jhet.5570360505

Reference yield: 94.0%

4-hydrazino-3-nitropyridine (33544-42-2) → 3,4-diaminopyridine (54-96-6)

Guidance literature:

With hydrogen; nickel; In ethanol; at 20 - 50 ℃; for 2h; under 3102.9 Torr;

DOI:10.1002/jhet.5570230306

Reference yield: 76.0%

4-(benzylamino)-3-nitropyridine (100306-70-5) → 3,4-diaminopyridine (54-96-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 80 ℃; for 30h; under 3102.9 Torr;

DOI:10.1002/jhet.5570230306

upstream raw materials:

4-amino-3-nitropyridine

4-hydrazino-3-nitropyridine

4-(benzylamino)-3-nitropyridine

4-aminopyridine

Downstream raw materials:

Imidazo<4,5-c>pyridin

pyrido[3,4-b]pyrazine

2-Phenyl-1H-imidazo<4,5-c>pyridine

2-(4-methoxy-phenyl)-1⁽³⁾H-imidazo[4,5-c]pyridine

Refernces

• 1、 -. "AMIFAMPRIDINE DIHYDROCHLORIDE". Page/Page column 16. . Retrieved 2017/11/03.
• 2、 -. "QUINOXALINONES AND DIHYDROQUINOXALINONES AS RESPIRATORY SYNCYTIAL VIRUS ANTIVIRAL AGENTS". Page/Page column 25. . Retrieved 2014/08/07.