| Identification | More | [Name]
3,4-Diaminopyridine | [CAS]
54-96-6 | [Synonyms]
3,4-DIAMINOPYRIDINE
3-AMINO-4-PYRIDINYLAMINE
ASINEX-REAG BAS 01447204
DIAMINOPYRIDINE(3,4-)
PYRIDINE-3,4-DIAMINE
TIMTEC-BB SBB004341
3,4-diamino-pyridin
3,4-pyridinediamine
4,5-diaminopyridine
diamino-3,4pyridine
3,4-DIAMINOPYRIDINE 98+%
3,4-DIAMINE-PYRIDINE
3,4-Pyridinedramine | [EINECS(EC#)]
200-220-9 | [Molecular Formula]
C5H7N3 | [MDL Number]
MFCD00006401 | [Molecular Weight]
109.13 | [MOL File]
54-96-6.mol |
| Chemical Properties | Back Directory | [Appearance]
brownish to brown-grey crystalline powder | [Melting point ]
216-218 °C (lit.) | [Boiling point ]
194.6°C (rough estimate) | [density ]
1.1118 (rough estimate) | [refractive index ]
1.5340 (estimate) | [Fp ]
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) | [Detection Methods]
HPLC | [Merck ]
14,2986 | [BRN ]
110232 | [CAS DataBase Reference]
54-96-6(CAS DataBase Reference) | [Storage Precautions]
Light sensitive;Store under nitrogen |
| Questions And Answer | Back Directory | [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 . |
| Safety Data | Back Directory | [Hazard Codes ]
T+,T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
R26:Very Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [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 |
| Hazard Information | Back Directory | [Chemical Properties]
brownish to brown-grey crystalline powder | [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.] |
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