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D7148

Sigma-Aldrich

3,4-Diaminopyridine

≥98%

Synonym(s):

3,4-DAP, 4,5-Diaminopyridine, Amifampridine, DAP, Pyridine-4,5-diamine

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About This Item

Empirical Formula (Hill Notation):
C5H7N3
CAS Number:
54-96-6
Molecular Weight:
109.13
Beilstein:
110232
EC Number:
200-220-9
MDL number:
MFCD00006401
UNSPSC Code:
12352100
PubChem Substance ID:
57654120
NACRES:
NA.22

Assay

≥98%

form

powder

mp

216-218 °C (lit.)

SMILES string

Nc1ccncc1N

InChI

1S/C5H7N3/c6-4-1-2-8-3-5(4)7/h1-3H,7H2,(H2,6,8)

InChI key

OYTKINVCDFNREN-UHFFFAOYSA-N

Gene Information

human ... KCNA1(3736) , KCNA10(3744) , KCNA2(3737) , KCNA3(3738) , KCNA4(3739) , KCNA5(3741) , KCNA6(3742) , KCNA7(3743) , KCNB1(3745) , KCNB2(9312) , KCNC1(3746) , KCNC2(3747) , KCNC3(3748) , KCNC4(3749) , KCND1(3750) , KCND2(3751) , KCND3(3752) , KCNF1(3754) , KCNG1(3755) , KCNG2(26251) , KCNG3(170850) , KCNG4(93107) , KCNH1(3756) , KCNH2(3757) , KCNH3(23416) , KCNH4(23415) , KCNH5(27133) , KCNH6(81033) , KCNH7(90134) , KCNH8(131096) , KCNQ1(3784) , KCNQ2(3785) , KCNQ3(3786) , KCNQ4(9132) , KCNQ5(56479) , KCNS1(3787) , KCNS2(3788) , KCNS3(3790) , KCNV1(27012) , KCNV2(169522)

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Application

3,4-Diaminopyridine can be used as a heterocyclic building block to prepare:      
  • Imidazo[4,5-c]pyridine, an important scaffold used for the preparation of CP-885316.     
  • 9-Azajulolidine derivatives, which are used as efficient organocatalysts for acylation and aza-Morita-Baylis-Hillman reaction.      
  • 2-Phenylpyrido[3,4-b]pyrazine by condensation reaction with α-methylsulfinylacetophenone in benzene/acetic acid as a solvent.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H330,H311,H319

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Eye Irrit. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Regioselective Synthesis of an Imidazo [4, 5-c] pyridine through Selective Acylation of 3, 4-Diaminopyridine: Synthesis of CP-885,316
Caron S, et al.
Organic Process Research & Development, 10(2), 257-261 (2006)
Monika Cecilija Žužek et al.
Toxicology letters, 281, 95-101 (2017-09-25)
The effects of natural polymeric alkylpyridinium salt (nPoly-3-APS), a potent acetylcholinesterase inhibitor isolated from the marine sponge Reniera sarai, were studied on isolated mouse phrenic nerve-hemidiaphragm muscle preparations using electrophysiological approaches. nPoly-3-APS inhibited nerve-evoked isometric muscle twitch and tetanic contraction
Fujun Luo et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(31), 11268-11281 (2011-08-05)
We used high-resolution fluorescence imaging and single-pixel optical fluctuation analysis to estimate the opening probability of individual voltage-gated calcium (Ca(2+)) channels during an action potential and the number of such Ca(2+) channels within active zones of frog neuromuscular junctions. Analysis
A Quartel et al.
Current medical research and opinion, 26(6), 1363-1375 (2010-04-10)
Lambert-Eaton myasthenic syndrome (LEMS) is a rare pre-synaptic auto-immune disorder of neuromuscular transmission that is characterised by proximal muscle weakness, depressed tendon reflexes and autonomic dysfunction. This review summarises the clinical symptoms, aetiology, diagnosis and treatment options for LEMS. Focus
Maarten J Titulaer et al.
The Lancet. Neurology, 10(12), 1098-1107 (2011-11-19)
Lambert-Eaton myasthenic syndrome (LEMS) is a neuromuscular autoimmune disease that has served as a model for autoimmunity and tumour immunology. In LEMS, the characteristic muscle weakness is thought to be caused by pathogenic autoantibodies directed against voltage-gated calcium channels (VGCC)
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