4-Aminopyridine
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Basic Info
| Common Name | 4-Aminopyridine(F06147) |
| 2D Structure | |
| FRCD ID | F06147 |
| CAS Number | 504-24-5 |
| PubChem CID | 1727 |
| Formula | C5H6N2 |
| IUPAC Name | pyridin-4-amine |
| InChI Key | NUKYPUAOHBNCPY-UHFFFAOYSA-N |
| InChI | InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7) |
| Canonical SMILES | C1=CN=CC=C1N |
| Isomeric SMILES | C1=CN=CC=C1N |
| Synonyms |
4-aminopyridine
4-Pyridylamine
504-24-5
pyridin-4-amine
Fampridine
4-Pyridinamine
Dalfampridine
Avitrol
p-Aminopyridine
4-AP
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Aminopyridines and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aminopyridines and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Aminopyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 94.117 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 48 |
| Monoisotopic Mass | 94.053 |
| Exact Mass | 94.053 |
| XLogP | 0.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 7 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9544 |
| Human Intestinal Absorption | HIA+ | 0.9610 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Non-substrate | 0.8619 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9916 |
| Non-inhibitor | 0.9885 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8423 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7249 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8832 |
| CYP450 2D6 Substrate | Non-substrate | 0.8870 |
| CYP450 3A4 Substrate | Non-substrate | 0.8181 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8657 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9070 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.7984 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8637 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8154 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9785 |
| Non-inhibitor | 0.9385 | |
| AMES Toxicity | Non AMES toxic | 0.5720 |
| Carcinogens | Non-carcinogens | 0.8220 |
| Fish Toxicity | Low FHMT | 0.8601 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8846 |
| Honey Bee Toxicity | Low HBT | 0.7997 |
| Biodegradation | Not ready biodegradable | 0.9426 |
| Acute Oral Toxicity | I | 0.7830 |
| Carcinogenicity (Three-class) | Non-required | 0.6315 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.4772 | LogS |
| Caco-2 Permeability | 1.6223 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5498 | LD50, mol/kg |
| Fish Toxicity | 2.4676 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.5139 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Sunflower Seeds | Japan | 0.1ppm | |||
| Corn(Maize) | Japan | 0.1 ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Parallel Evaluation of Two Potassium Channel Blockers in Restoring Conduction in Mechanical Spinal Cord Injury in Rat. | J Neurotrauma | 2018 May 1 | 29228863 |
| Hyperpolarization by N-(3-oxododecanoyl)-l-homoserine-lactone, a quorum sensing molecule, in rat thymic lymphocytes. | Chem Biol Interact | 2018 Mar 1 | 29427588 |
| Evidence of K+ homeostasis disruption in cellular dysfunction triggered by7-ketocholesterol, 24S-hydroxycholesterol, and tetracosanoic acid (C24:0) in 158Nmurine oligodendrocytes. | Chem Phys Lipids | 2017 Oct | 28322741 |
| Capsaicin presynaptically inhibits glutamate release through the activation ofTRPV1 and calcineurin in the hippocampus of rats. | Food Funct | 2017 May 24 | 28418433 |
| Characterization of ion channels on subesophageal ganglion neurons from Chinese tarantula Ornithoctonus huwena: Exploring the myth of the spider insensitive to its venom. | Toxicon | 2016 Sep 15 | 27452932 |
| Voltage-operated potassium (Kv) channels contribute to endothelium-dependentvasorelaxation of carvacrol on rat aorta. | J Pharm Pharmacol | 2016 Sep | 27334686 |
| Xanthohumol-induced presynaptic reduction of glutamate release in the rathippocampus. | Food Funct | 2016 Jan | 26667007 |
| Myricetin inhibits the release of glutamate in rat cerebrocortical nerveterminals. | J Med Food | 2015 May | 25340625 |
| A Massive Overdose of Dalfampridine. | West J Emerg Med | 2015 Dec | 26759675 |
| Bromethalin poisoning in a raccoon (Procyon lotor): diagnostic considerations andrelevance to nontarget wildlife. | J Vet Diagn Invest | 2014 Jan | 24323056 |
| Coenzyme Q10 inhibits the release of glutamate in rat cerebrocortical nerveterminals by suppression of voltage-dependent calcium influx andmitogen-activated protein kinase signaling pathway. | J Agric Food Chem | 2012 Dec 5 | 23167655 |
| Chronic stress enhances calcium mobilization and glutamate exocytosis incerebrocortical synaptosomes from mice. | Neurol Res | 2011 Nov | 22080989 |
| Ethanol extract of seeds of Oenothera odorata induces vasorelaxation viaendothelium-dependent NO-cGMP signaling through activation of Akt-eNOS-sGCpathway. | J Ethnopharmacol | 2011 Jan 27 | 20932888 |
| New drugs: Liraglutide, dalfampridine, and abobotulinumtoxinA. | J Am Pharm Assoc (2003) | 2010 May-Jun | 20452924 |
| Acute restraint stress enhances calcium mobilization and glutamate exocytosis in cerebrocortical synaptosomes from mice. | Neurochem Res | 2010 May | 20069359 |
| Astaxanthin inhibits glutamate release in rat cerebral cortex nerve terminals viasuppression of voltage-dependent Ca(2+) entry and mitogen-activated proteinkinase signaling pathway. | J Agric Food Chem | 2010 Jul 28 | 20593829 |
| Endothelium-independent vasodilation induced by kolaviron, a biflavonoid complex from Garcinia kola seeds, in rat superior mesenteric arteries. | J Smooth Muscle Res | 2009 Feb | 19377272 |
| Rapid effects of 1alpha,25(OH)2D3 in resting human peripheral blood mononuclearcells. | Eur J Pharmacol | 2008 May 31 | 18353308 |
| Currents contributing to decision making in neurons B31/B32 of Aplysia. | J Neurophysiol | 2008 Feb | 18032563 |
| Experimental diabetes enhances Ca2+ mobilization and glutamate exocytosis in cerebral synaptosomes from mice. | Diabetes Res Clin Pract | 2008 Aug | 18508149 |