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Chemical Structure| 54-96-6

Chemical Structure| 54-96-6

Chemical Structure| 54-96-6

*Storage: Keep in dark place,Inert atmosphere,Room temperature.

Amifampridine

CAS No.: 54-96-6

Amifampridine is a quaternary ammonium compound that blocks presynaptic potassium channels, subsequently prolongs the action potential and increases presynaptic calcium concentrations, it was approved by the US FDA for the treatment of adults with LEMS.

Synonyms: 3,4-Diaminopyridine

4.5 *For Research Use Only !

Cat. No.: A101083 Purity: 98%

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Quality Control of [ 54-96-6 ] Purity: 98% SDS Specification

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Product Details of [ 54-96-6 ]

CAS No. :	54-96-6
Formula :	C₅H₇N₃
M.W :	109.13
SMILES Code :	C1=CN=CC(=C1N)N
Synonyms :	3,4-Diaminopyridine
MDL No. :	MFCD00006401
InChI Key :	OYTKINVCDFNREN-UHFFFAOYSA-N
Pubchem ID :	5918

Safety of [ 54-96-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H300+H330-H311-H315-H319-H335
Precautionary Statements:	P260-P264-P280-P284-P301+P310-P305+P351+P338
Class:	6.1
UN#:	2811
Packing Group:	Ⅱ

Calculated chemistry of [ 54-96-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	33.05
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	64.93 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.57
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	-0.51
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.26
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.86
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	0.01
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.1

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.75
Solubility	19.4 mg/ml ; 0.178 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.39
Solubility	44.9 mg/ml ; 0.412 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.24
Solubility	6.25 mg/ml ; 0.0573 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.33 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.33

Application In Synthesis [ 54-96-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 54-96-6 ]
Downstream synthetic route of [ 54-96-6 ]

[ 54-96-6 ] Synthesis Path-Upstream 1~1

1
[ 54-96-6 ]
[ 1590409-73-6 ]

References: [1] Patent: US2014/94456, 2014, A1, .
[2] Patent: WO2015/153683, 2015, A1, .

[ 54-96-6 ] Synthesis Path-Downstream 1~11

1
[ 54-96-6 ]
[ 50-00-0 ]
[ 272-97-9 ]

References: [1]Chemische Berichte,1938,vol. 71,p. 2347,2358.

2
[ 54-96-6 ]
[ 64-18-6 ]
[ 272-97-9 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 9532 - 9533.
[2]Journal of Natural Products,2013,vol. 76,p. 1637 - 1646.
[3]Journal of the Chemical Society,1956,p. 4683.
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5023 - 5026.

3
[ 54-96-6 ]
[ 570-02-5 ]
[ 89075-21-8 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 717 - 727.

4
[ 54-96-6 ]
[ 448-36-2 ]
[ 95420-55-6 ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 717 - 727.

5
[ 54-96-6 ]
[ 3973-08-8 ]
[ 65911-26-4 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 511 - 522.

6
[ 54-96-6 ]
[ 89792-18-7 ]
[ 272-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	With formic acid; calcium carbonate; In ethanol;	Preparation of imidazo[4,5-c]pyridine (IV) An example of a specific method for preparation of the imidazo[4,5-c]pyridine intermediate, from which the general preparation of intermediate (IV), above, may be derived, is as follows: A stirred mixture of 3,4-diaminopyridine (10.0 g, 0.092 mol) and formic acid (20 ml) was heated under reflux for 2.5 hours. The resulting mixture was cooled and the formic acid was evaporated off under reduced pressure to yield a residue. The residue was dissolved in ethanol (30 ml) at 80C and the resulting solution was treated with calcium carbonate (10 g) and neutralized by stirring under reflux for 1 hour. The hot mixture was filtered and the residue was washed with hot ethanol (3 x 300 ml). The filtrate and washings were combined and the ethanol was evaporated off under reduced pressure to yield 3,4-diformylaminopyridine as a colorless solid. The 3,4-diformylaminopyridine was heated at 200-220C and 66.5 Pa (0.5 mm Hg) pressure in a Kugelrohr bulb-to-bulb distillation apparatus to yield a crude product as a distillate which solidified on cooling. The crude product was recrystallized from ethyl acetate to yield imidazo[4,5-c]pyridine as a colorless crystalline solid, having a melting point of 174-176C and the following physical characteristics: 1H-NMR (delta, DMSO-d6: 6.60 (broad s,1H), 7.66 (dd,1H), 8.37 (d,1H), 8.44 (s,1H) and 9.00 (d,1H).

References: [1]Patent: EP404797,1995,B1 .

7
[ 54-96-6 ]
[ 2991-28-8 ]
[ 1275249-07-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5111 - 5114.

8
[ 54-96-6 ]
[ 124-38-9 ]
[ 272-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N?-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; phenylsilane; In tetrahydrofuran; at 70℃; under 750.075 - 2250.23 Torr; for 24h;Schlenk technique; Inert atmosphere; Glovebox;	General procedure: A-Synthesis of Benzimidazole and Derivatives from Aromatic 1,2-DiaminesThe first results presented describe the synthesis of benzimidazole rings and derivatives from aromatic 1,2-diamines. In this case, the amine R1NH2 and the nitrogenous nucleophilic agent R5R6NH are two reactive functional groups of one and the same molecule (diamine) and are thus connected via a covalent bond. This bond is preferably an aromatic ring of benzene, pyridine or pyrimidine type and the ring formed during the reaction is a nitrogenous heterocycle comprising 5 atoms of imidazole type. In the case where the nucleophile is oxygen-based (R7OH), the rings obtained are benzoxazoles. The results presented were produced by preferably using two sources of different reducing agents, polymethylhydrosiloxane (PMHS), sold by Aldrich under the reference 176206, and phenylsilane (PhSiH3), sold by Aldrich. In the case of the PMHS, as a silane is a polymer, the number of equivalents introduced is given with respect to the number of hydrides introduced and thus the number of monomers introduced with respect to the amine. Thus, the introduction of 3 equivalents of PMHS corresponds to the introduction of 3 equivalents of hydride and thus 3 equivalents of monomers of the PMHS with respect to the amine. Different (pre)catalysts were tested for the reaction.

References: [1]ChemCatChem,2013,vol. 5,p. 117 - 120.
[2]Patent: US2015/148535,2015,A1 .Location in patent: Paragraph 0192; 0193.

9
[ 54-96-6 ]
[ 122-51-0 ]
[ 272-97-9 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of pyridine-3,4-diamine (2?g, 18.3?mmol) and triethyl orthoformate (50?mL) was refluxed for about 3?h?at 145?C. After completion of the reaction monitored by TLC, 2?mL of formic acid was added and the mixture was refluxed at the same temperature for another 2?h. The solution was evaporated to dryness at reduced pressure, and the residue was dissolved in methanol and stirred at room temperature overnight in presence of charcoal. Following removal of the charcoal by vacuum filtration through celite-545, the filtrate was evaporated to give the title compound 2 as an off-white solid in quantitative yield without further purification. 1H NMR (300?MHz, DMSO-d6) delta 8.97 (d, J?=?1.1?Hz, 1H), 8.32 (d, J?=?5.6?Hz, 1H), 7.61 (dd, J?=?5.6, 1.1?Hz, 1H); 13C NMR (75?MHz, DMSO) delta 144.35, 141.18 (2?*?C, overlapped), 139.72, 137.73, 109.46. HRMS (ESI): m/z calcd. for C6H6N3 [M+H]+: 120.0556; found, 120.0556.

References: [1]ChemMedChem,2013,vol. 8,p. 985 - 993.
[2]European Journal of Medicinal Chemistry,2018,vol. 148,p. 384 - 396.

10
[ 54-96-6 ]
[ 1007128-70-2 ]

References: [1]Patent: WO2015/153683,2015,A1 .

11
[ 54-96-6 ]
[ 68-12-2 ]
[ 272-97-9 ]

References: [1]New Journal of Chemistry,2016,vol. 40,p. 8282 - 8287.

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P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

✕

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere