Showing Compound Card for 4-Dimethylaminopyridine (CDB005485)

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Record Information
Version1.0
Created at2020-04-27 16:25:17 UTC
Updated at2021-01-04 20:37:44 UTC
CannabisDB IDCDB005485
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Dimethylaminopyridine
Description4-Dimethylaminopyridine, also known as 4-DMAP or DMAP, belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. 4-DMAP is one of several isomers of dimethylaminopyridine wherein the dimethylamino group is located at different positions around the pyridine ring relative to the pyridine nitrogen group. DMAP is a colorless solid that is strongly basic – more basic than pyridine itself. Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement, Staudinger synthesis of β-lactams and many more. DMAP is an exceptional catalyst for a host of electrophilic substitution reactions and is a well-known acylation catalyst. DMAP can be prepared in a two-step procedure from pyridine, which is first oxidized to 4-pyridylpyridinium cation. It is soluble in water, methanol, benzene, ethyl acetate, chloroform, methylene chloride, acetone, and acetic acid. DMAP has a relatively high toxicity and is particularly dangerous because of its ability to be absorbed through the skin. 4-(Dimethylamino)pyridine is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-DMAPMeSH
4-DimethylaminopyridineMeSH
Chemical FormulaC7H10N2
Average Molecular Weight122.17
Monoisotopic Molecular Weight122.0844
IUPAC NameN,N-dimethylpyridin-4-amine
Traditional Name4-dimethylaminopyridine
CAS Registry Number1122-58-3
SMILES
CN(C)C1=CC=NC=C1
InChI Identifier
InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
InChI KeyVHYFNPMBLIVWCW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Aminopyridine
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.36ALOGPS
logP0.86ChemAxon
logS0.63ALOGPS
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.33 m³·mol⁻¹ChemAxon
Polarizability13.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Dimethylaminopyridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9800000000-2dfbdbd512c001f94ffbSpectrum
Predicted GC-MS4-Dimethylaminopyridine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 8V, positivesplash10-00di-0900000000-8f55626aef827e90a6532020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 15V, positivesplash10-00di-0900000000-1a1c321643f2645d59192020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-00di-0900000000-8498339f781026648dfd2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-00di-0900000000-0ed5bf6356ea73b89bf32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-00di-0900000000-cf6ade7eddcad27daab62020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-00di-0900000000-2d848dcc16e453d5b9032020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 19V, positivesplash10-00di-0900000000-1d38cf671e0451c2ae3c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-00di-0900000000-d857f2eb7cbd044f86032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-00di-0900000000-0313a98709a21b4799432020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-00di-1900000000-60f28386c8cf50b346ab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-00di-1900000000-b8f7943fe21bbbb3db862020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-05i0-2900000000-b703b15af69106e20cbf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-0adi-3900000000-171bf4969de9b1bab95b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 22V, positivesplash10-0a6r-4900000000-6e7ab0b8ed94212f484a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 24V, positivesplash10-0a6r-5900000000-5e72fddbd0e0ed85a2702020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 26V, positivesplash10-0a6r-6900000000-f16f415e73308abee6952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 28V, positivesplash10-0a6r-7900000000-7016dc6d86e61301adba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 30V, positivesplash10-056r-9800000000-ea75b977bc8e9abcfb2b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 32V, positivesplash10-056r-9600000000-20012dff1ad59829c5b82020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-65ca583c5b68262a0f862016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-c4555998fb5accd174c12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uka-9300000000-5832a69ea31e5ea7ed912016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-bf07defc5621881d5ade2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-20c09674617c1b026c7a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-6900000000-ff9f8719b5d0cd80da8b2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14284
PDB IDNot Available
ChEBI IDNot Available
References
General ReferencesNot Available