Description Uses Mechanism of action Pharmacokinetics Toxicty
ChemicalBook > CAS DataBase List > 3,4-Diaminopyridine

3,4-Diaminopyridine

Description Uses Mechanism of action Pharmacokinetics Toxicty
Product Name
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
Formula Weight
109.13
MOL File
54-96-6.mol
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3,4-Diaminopyridine Property

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
form 
Crystalline Powder
pka
9.17±0.12(Predicted)
color 
Brownish to brown-gray
Water Solubility 
24 g/L (20 ºC)
Merck 
14,2986
BRN 
110232
InChI
InChI=1S/C5H7N3/c6-4-1-2-8-3-5(4)7/h1-3H,7H2,(H2,6,8)
InChIKey
OYTKINVCDFNREN-UHFFFAOYSA-N
SMILES
C1=NC=CC(N)=C1N
CAS DataBase Reference
54-96-6(CAS DataBase Reference)
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Safety

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
F 
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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H311Toxic in contact with skin

H319Causes serious eye irritation

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D7148
Product name
3,4-Diaminopyridine
Purity
≥98%
Packaging
1g
Price
$38.5
Updated
2024/03/01
Sigma-Aldrich
Product number
D7148
Product name
3,4-Diaminopyridine
Purity
≥98%
Packaging
5g
Price
$123
Updated
2024/03/01
Sigma-Aldrich
Product number
8.18392
Product name
3,4-Diaminopyridine
Purity
for synthesis
Packaging
1g
Price
$46.8
Updated
2024/03/01
Sigma-Aldrich
Product number
8.18392
Product name
3,4-Diaminopyridine
Purity
for synthesis
Packaging
5G
Price
$183
Updated
2024/03/01
TCI Chemical
Product number
D1149
Product name
3,4-Diaminopyridine
Purity
>99.0%(GC)(T)
Packaging
1g
Price
$35
Updated
2024/03/01
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3,4-Diaminopyridine Chemical Properties,Usage,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.

Definition

ChEBI: Amifampridine is an aminopyridine.

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.

Purification Methods

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

3,4-Diaminopyridine Preparation Products And Raw materials

Raw materials

FUMING SULFURIC ACID Ammonium hydroxide Palladium 4-Hydroxypyridine 4-Amino-3-nitropyridine Phosphorus pentachloride Nitric acid Methanol Ammonium acetate

Preparation Products

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View Lastest Price from 3,4-Diaminopyridine manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
3,4-Diaminopyridine 54-96-6
Price
US $100.00/KG
Min. Order
1KG
Purity
99%min
Supply Ability
200TON
Release date
2024-11-08
Hebei Mojin Biotechnology Co.,Ltd
Product
3,4-Diaminopyridin 54-96-6
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
50000KG/month
Release date
2024-09-26
Shaanxi Dideu Medichem Co. Ltd
Product
3,4-Diaminopyridine 54-96-6
Price
US $1.10/g
Min. Order
1g
Purity
99.0% min
Supply Ability
100 tons min
Release date
2021-04-30

54-96-6, 3,4-DiaminopyridineRelated Search:

4-Dimethylaminopyridine Diaminopyridine,2 6-DIAMINOPYRIDINE 99+% &,2,6-Diaminopyridine,>98%,2,6-Diaminopyridine 3-Aminopyridine Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate Iminodiacetonitrile 2-Aminopyridine 2,5-DIAMINOPYRIDINE 2,3-DIAMINOPYRIDINE,2,3-Diaminopyridine,98%,2,3-Diaminopyridine99% 4-AMINO-3-NITROQUINOLINE 2,4-DIAMINOPYRIDINE 4-Amino-3-nitropyridine 3,4-DIAMINOQUINOLINE Oxifungin Elbanizine 6-chloropyridine-3,4-diamine hydrochloride 2-CHLORO-N4-METHYLPYRIDINE-3,4-DIAMINE 3,5-Difluoropyridine-2,6-diamine 3-NITRO-4-PIPERIDIN-1-YLPYRIDINE

  • 3,4-diamino-pyridin
  • 3,4-pyridinediamine
  • Pyridine, 3,4-diamino-
  • WLN: T6NJ CZ DZ
  • 3,4-Diaminopyridine C5H7N3
  • 4,5-diaminopyridine
  • diamino-3,4pyridine
  • TIMTEC-BB SBB004341
  • PYRIDINE-3,4-DIAMINE
  • 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
  • Amifampridine
  • 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 &gt
  • 3,4-Diaminopyridine, 98%, for synthesis
  • 3,4-Diaminopyridine ISO 9001：2015 REACH
  • TIANFU-CHEM - 3,4-Diaminopyridine
  • 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