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3,4-Diaminopyridine

CAS No.
54-96-6
Chemical Name:
3,4-Diaminopyridine
Synonyms
Amifampridine;PYRIDINE-3,4-DIAMINE;3,4-diamino-pyridin;3,4-DAP;NSC 521760;Amipyridine;WLN: T6NJ CZ DZ;TIMTEC-BB SBB004341;diamino-3,4pyridine;4,5-diaminopyridine
CBNumber:
CB6676074
Molecular Formula:
C5H7N3
Molecular Weight:
109.13
MDL Number:
MFCD00006401
MOL File:
54-96-6.mol
MSDS File:
SDS
Last updated:2024-03-22 17:12:53

3,4-Diaminopyridine Properties

Melting point 216-218 °C (lit.)
Boiling point 194.6°C (rough estimate)
Density 1.1118 (rough estimate)
refractive index 1.5340 (estimate)
Flash point 240 °C
storage temp. Store below +30°C.
solubility 30g/l
pka 9.17±0.12(Predicted)
form Crystalline Powder
color Brownish to brown-gray
Water Solubility 24 g/L (20 ºC)
Merck 14,2986
BRN 110232
CAS DataBase Reference 54-96-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII RU4S6E2G0J
NCI Drug Dictionary amifampridine
ATC code N07XX05

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300+H330-H311-H319
Precautionary statements  P260-P264-P280-P302+P352+P312-P304+P340+P310-P305+P351+P338
Hazard Codes  T+,T,Xi
Risk Statements  25-26-36/37/38
Safety Statements  26-28-36/37/39-45-37/39-28A-36
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
RTECS  US7600000
10-23
Autoignition Temperature 480 °C
Hazard Note  Irritant
HazardClass  6.1
PackingGroup  I
HS Code  29333999
Toxicity LD50 orally in Rabbit: 47 mg/kg LD50 dermal Rabbit > 200 mg/kg
NFPA 704
1
4 0

3,4-Diaminopyridine price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D7148 3,4-Diaminopyridine ≥98% 54-96-6 1g $38.5 2024-03-01 Buy
Sigma-Aldrich D7148 3,4-Diaminopyridine ≥98% 54-96-6 5g $123 2024-03-01 Buy
Sigma-Aldrich 8.18392 3,4-Diaminopyridine for synthesis 54-96-6 1g $46.8 2024-03-01 Buy
Sigma-Aldrich 8.18392 3,4-Diaminopyridine for synthesis 54-96-6 5G $183 2024-03-01 Buy
TCI Chemical D1149 3,4-Diaminopyridine >99.0%(GC)(T) 54-96-6 1g $35 2024-03-01 Buy
Product number Packaging Price Buy
D7148 1g $38.5 Buy
D7148 5g $123 Buy
8.18392 1g $46.8 Buy
8.18392 5G $183 Buy
D1149 1g $35 Buy

3,4-Diaminopyridine Chemical Properties,Uses,Production

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.

Mechanism of action

Amifampridine works by blocking potassium channel efflux in nerve terminals so that action potential duration is increased. Ca2+ channels can then be open for a longer time and allow greater acetylcholine release to stimulate muscle at the end plate.

Pharmacokinetics

Administration of amifampridine to patients with LES in clinical trials resulted in improvement of the compound muscle action potential (CMAP), muscle function, and quantitative myasthenia gravis (QMG) score . One case of a slight prolongation of the QTc interval in male patient with LEMS and euthyroid Hashimoto’s disease treated with 90 mg of amifampridine in combination with 100 mg azathioprine was reported . In vitro, amifampridine was shown to modulate cardiac conduction and induce phasic contractions in different arteries from several species. In addition, it stimulated potassium-evoked dopamine and noradrenaline release in rat hippocampal slices and upregulate acetylcholine release in the brain. It may also potentiate adrenergic and cholinergic neuromuscular transmission in the gatrointestinal tract. In a single pharmacokinetic study, no effect was observed of amifampridine phosphate on cardiac repolarization as assessed using the QTc interval . There were no changes in heart rate, atrioventricular conduction or cardiac depolarization as measured by the heart rate, PR and QRS interval durations.

Toxicty

The approximate oral LD50 was >25mg/kg in rats and 100 mg/kg in mice. The approximate intravenous LD50 was 25 mg/kg in both rats and mice. Peritoneal and subcutaneous LD50 in mice were 20 mg/kg and 35 mg/kg, respectively. There is limited clinical experienced with amifampridine overdose. The manifestations of acute drug overdose may include abdominal pain, and should be responded with discontinuation of treatment and initiation of supportive care with close monitoring of viral signs. There is no specific antidote known for amifampridine .

Chemical Properties

brownish to brown-grey crystalline powder

Uses

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.

Definition

ChEBI: Amifampridine is an aminopyridine.

Purification Methods

It crystallises from *benzene and is stored under N2 because it is deliquescent and absorbs CO2. [Beilstein 22/11 V 266.]

1681-37-4
54-96-6
Synthesis of 3,4-Diaminopyridine from 4-Amino-3-nitropyridine
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View Lastest Price from 3,4-Diaminopyridine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3,4-Diaminopyridine pictures 2024-04-17 3,4-Diaminopyridine
54-96-6
US $1.10 / g 1g 99.0% min 100 tons min Shaanxi Dideu Medichem Co. Ltd
3,4-Diaminopyridine pictures 2024-03-23 3,4-Diaminopyridine
54-96-6
US $34.00-1.20 / kg 1kg 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
3,4-Diaminopyridine pictures 2023-07-05 3,4-Diaminopyridine
54-96-6
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
3,4-pyridinediamine Pyridine, 3,4-diamino- WLN: T6NJ CZ DZ 4,5-diaminopyridine diamino-3,4pyridine TIMTEC-BB SBB004341 DIAMINOPYRIDINE(3,4-) ASINEX-REAG BAS 01447204 3-AMINO-4-PYRIDINYLAMINE 3,4-DIAMINOPYRIDINE 3,4-DIAMINOPYRIDINE 98+% 3,4-DIAMINE-PYRIDINE 3,4-Pyridinedramine NSC 521760 pyridin-3,4-diaMine 3,4-DIAMINOPYRIDINE FOR SYNTHESIS Pyridine-4,5-diaMine 3,4- twoaMinopyridine (3-amino-4-pyridyl)amine 3,4-DAP 3,4-Pyridinediamine (9CI) 3,4-Diaminopyridine C5H7N3 3,4-Diaminopyridine > 3,4-Diaminopyridine, 98%, for synthesis 3,4-Diaminopyridine ISO 9001:2015 REACH TIANFU-CHEM - 3,4-Diaminopyridine 3,4-diamino-pyridin PYRIDINE-3,4-DIAMINE Amifampridine 3,4-Diamino[3,4-b]pyridine Fampridine Impurity 20 Amipyridine Amifampridin, (3,4-Diaminopyridin) 54-96-6 Building Blocks C5 Heterocyclic Building Blocks Pyridines Boronic Acid pyridine series Building Blocks C5 Chemical Synthesis Heterocyclic Building Blocks Pyridine Pyridines, Pyrimidines, Purines and Pteredines Amines Pyridines bc0001