Record Information
Version1.0
Creation date2010-04-08 22:10:14 UTC
Update date2020-09-17 15:35:17 UTC
Primary IDFDB012557
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsoquinoline
DescriptionIsoquinoline, also known as 2-benzazine, belongs to the class of organic compounds known as isoquinolines and derivatives. Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. Isoquinoline is a weak basic compound (based on its pKa). Being an analog of pyridine, isoquinoline is a weak base, with a pKb of 8.6. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3. Isoquinoline is a colorless hygroscopic liquid at room temperature with a penetrating, unpleasant odor. Impure samples can appear brownish, as is typical for nitrogen heterocycles. It crystallizes as platelets that poorly soluble in water but dissolve well in organic solvents such as ethanol, acetone, and diethyl ether. It is also soluble in diluted acids, due to the formation of the protonated salt derivative. 1-Benzylisoquinoline is the structural backbone in naturally occurring alkaloids including papaverine and morphine. The isoquinoline ring in these natural compounds derives from the aromatic amino acid tyrosine.
CAS Number119-65-3
Structure
Thumb
Synonyms
SynonymSource
2-BenzazineChEBI
Benzo[c]pyridineChEBI
IsochinolinChEBI
2-AzanaphthaleneHMDB
2-BenzanineHMDB
3,4-BenzopyridineHMDB
Benzo(c)pyridineHMDB
BenzopyridineHMDB
beta -QuinolineHMDB
beta-QuinolineHMDB
FEMA 2978HMDB
ISQHMDB
Isoquinoline sulfate (1:1)HMDB
Isoquinoline hydrobromideHMDB
Isoquinoline hydrochlorideHMDB
Isoquinoline hydroiodideHMDB
Isoquinoline conjugate acidHMDB
β-quinolinebiospider
Beta-quinolinebiospider
Predicted Properties
PropertyValueSource
Water Solubility2.81 g/LALOGPS
logP2.14ALOGPS
logP1.75ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.35 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H7N
IUPAC nameisoquinoline
InChI IdentifierInChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
InChI KeyAWJUIBRHMBBTKR-UHFFFAOYSA-N
Isomeric SMILESC1=CC=C2C=NC=CC2=C1
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
Classification
Description Belongs to the class of organic compounds known as isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassNot Available
Direct ParentIsoquinolines and derivatives
Alternative Parents
Substituents
  • Isoquinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 83.69%; H 5.46%; N 10.84%DFC
Melting PointMp 25.5-26°DFC
Boiling PointBp40 142°DFC
Experimental Water Solubility4.52 mg/mL at 25 oCPEARLMAN,RS et al. (1984)
Experimental logP2.08HANSCH,C ET AL. (1995)
Experimental pKapKa 5.4 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.1DFC
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIsoquinoline, non-derivatized, GC-MS Spectrumsplash10-0fb9-9700000000-153cb7989d20a5d305feSpectrum
GC-MSIsoquinoline, non-derivatized, GC-MS Spectrumsplash10-004i-5900000000-938e708f6f6371c89a90Spectrum
GC-MSIsoquinoline, non-derivatized, GC-MS Spectrumsplash10-0fb9-9700000000-153cb7989d20a5d305feSpectrum
GC-MSIsoquinoline, non-derivatized, GC-MS Spectrumsplash10-004i-5900000000-938e708f6f6371c89a90Spectrum
Predicted GC-MSIsoquinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ufr-0900000000-58fc23546d7bc648aaffSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-fe8f7e7494fe51834c73Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-53932d6a797b58065acfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-3bd6daf754e7fa1a6223Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-7900000000-c5e6dca63fceb0eb257aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-a4927588bd0391d5e768Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b36Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b36Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b36Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-43576b7775a986b95c7eSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ba509566033d258bb64Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a52113b66ca5a059f497Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-1631e63f0b49a1687150Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0f89-0900000000-95ee1aa2d6255c9ec936Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0ugi-4900000000-1dd979c3c8f2435edd6dSpectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9800000000-d91870148f53fbc1391aSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-bca894ecef9e1b2fb95eSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-87133a5da2b971403b8cSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-87133a5da2b971403b8cSpectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-aa2de101cd67d3fcfd39Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-d3baf54cc19e70a1ec07Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f58afd1811d8a3a4d0d7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-1900000000-4a2becbb485199b25f49Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b4be2f7dd0aed898ee51Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-b2a468601694a7ca84beSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-416ad6650d560fd35318Spectrum
NMRNot Available
ChemSpider ID8098
ChEMBL IDCHEMBL12315
KEGG Compound IDC06323
Pubchem Compound ID8405
Pubchem Substance IDNot Available
ChEBI ID16092
Phenol-Explorer IDNot Available
DrugBank IDDB04329
HMDB IDHMDB34244
CRC / DFC (Dictionary of Food Compounds) IDHHX52-V:HHX52-V
EAFUS ID1943
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDISQ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034341
SuperScent IDNot Available
Wikipedia IDIsoquinoline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
benzaldehyde
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
anise
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference