Showing Compound Card for 4-pyridinamine (CDB000541)

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Record Information
Version1.0
Created at2020-03-19 00:42:42 UTC
Updated at2020-11-18 16:35:15 UTC
CannabisDB IDCDB000541
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-pyridinamine
Description4-Aminopyridine (4-AP, fampridine, dalfampridine) is an organic compound with the chemical formula C5H4N–NH2. The molecule is one of the three isomeric amines of pyridine. 4-Aminopyridine is an aromatic amine, constituted by a pyridine ring system, bearing a single amino substituent at position 4. 4-Aminopyridine is a potassium channel blocker used clinically to help multiple sclerosis patients walk. After a phase III trial, a 25 % improvement in walking speed and increased muscular strength was reported in multiple sclerosis patients (PMID: 24587826 ). It is also widely used as a research tool for the characterization of subtypes of the potassium channel (PMID: 31919372 ). The production of 4-aminopyridine begins with the ammoxidation of 4-methylpyridine, followed by obtainment of the nitrile. The nitrile is then used to generate the pyridine carboxamide, which undergoes a decarboxylation reaction to yield 4-aminopyridine ( Ref:DOI ). 4-Aminopyridine has also been detected as one of the volatile components in marijuana samples obtained during police seizures (PMID:26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-APChEBI
4-PyridinamineChEBI
4-PyridylamineChEBI
AmpyraChEBI
AvitrolChEBI
FampridinaChEBI
FampridineChEBI
FampridinumChEBI
gamma-AminopyridineChEBI
N07XX07ChEBI
p-AminopyridineChEBI
4-AminopyridineKegg
NeurelanKegg
FampyraKegg
g-AminopyridineGenerator
Γ-aminopyridineGenerator
DalfampridineChEBI
4 AminopyridineMeSH
4 Aminopyridine sustained releaseMeSH
PymadineMeSH
Fampridine SRMeSH
Fampridine-SRMeSH
4-Aminopyridine sustained releaseMeSH
VMI 103MeSH
Sustained release, 4-aminopyridineMeSH
VMI-103MeSH
Chemical FormulaC5H6N2
Average Molecular Weight94.11
Monoisotopic Molecular Weight94.0531
IUPAC Name1,4-dihydropyridin-4-imine
Traditional Name4-aminopyridine
CAS Registry Number504-24-5
SMILES
N=C1C=CNC=C1
InChI Identifier
InChI=1S/C5H6N2/c6-5-1-3-7-4-2-5/h1-4H,(H2,6,7)
InChI KeyNUKYPUAOHBNCPY-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassAminopyridines and derivatives
Direct ParentAminopyridines and derivatives
Alternative Parents
Substituents
  • Aminopyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.65ALOGPS
logP0.29ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)16.04ChemAxon
pKa (Strongest Basic)12.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area35.88 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.09 m³·mol⁻¹ChemAxon
Polarizability9.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-8298bac1cfd86955d1ee2014-09-20View Spectrum
GC-MS4-pyridinamine, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-d76cf775a4e0c55c9a50Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0002-9000000000-38892360ceafd0620f652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0002-9000000000-51326f026124a275802e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0002-9000000000-bdf16d24f7f300bcac202020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0002-9000000000-5fc3bcf86f00669faf882020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0002-9000000000-66e0f38bd0aab60037df2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0002-9000000000-bcd6a6c53e7a2d9d34042020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-002b-9000000000-3fe4f715dfb6e091d7192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-002b-9000000000-a83c3015f770c5d5230b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-002b-9000000000-e6a43885cc1f15e8fa0c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-004j-9000000000-3ba9365c05683adc30672020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0fba-9000000000-89b6856fba31c7af98582020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-0fb9-9000000000-28ffe5713230b691f9002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0ufr-9000000000-0e5a60c0c7b08c359c502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 45V, positivesplash10-0udi-9000000000-a46456374bb11088cf772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 1V, positivesplash10-004i-9000000000-ddb0878d8656440d36152020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 2V, positivesplash10-004i-9000000000-2622d71d150ed8a3a3522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 3V, positivesplash10-004i-9000000000-2622d71d150ed8a3a3522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 4V, positivesplash10-004i-9000000000-2622d71d150ed8a3a3522020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 5V, positivesplash10-004i-9000000000-2622d71d150ed8a3a3522020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-b9ca65a501bd24b8adf52016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-5b9ddb3af3ab551845d82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9000000000-68383f33699a6453bc492016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-f240dc053a801a491f6c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-1b9fe497d4864ae333ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9000000000-ea15c905b0157a6e61152016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB06637
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC13728
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDalfampridine
METLIN IDNot Available
PubChem Compound1727
PDB IDNot Available
ChEBI ID34385
References
General References
  1. Jensen HB, Ravnborg M, Dalgas U, Stenager E: 4-Aminopyridine for symptomatic treatment of multiple sclerosis: a systematic review. Ther Adv Neurol Disord. 2014 Mar;7(2):97-113. doi: 10.1177/1756285613512712. [PubMed:24587826 ]
  2. Rodriguez-Rangel S, Bravin AD, Ramos-Torres KM, Brugarolas P, Sanchez-Rodriguez JE: Structure-activity relationship studies of four novel 4-aminopyridine K(+) channel blockers. Sci Rep. 2020 Jan 9;10(1):52. doi: 10.1038/s41598-019-56245-w. [PubMed:31919372 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]