Showing Compound Card for Isoquinoline (CDB000619)

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Record Information
Version1.0
Created at2020-03-19 00:46:59 UTC
Updated at2021-01-04 20:37:38 UTC
CannabisDB IDCDB000619
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsoquinoline
DescriptionIsoquinoline, also known as 2-benzazine or benzo[c]pyridine, 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 forming benzo[c]pyridine. Isoquinoline is also classified as a benzopyridine. It is a structural isomer of quinoline. Isoquinoline exists a colorless hygroscopic liquid at temperatures above its melting point (around 25 oC) with a penetrating, unpleasant odor. More specifically isoquinoline has a sweet, balsam, bitter almond or anise aroma. Impure samples of isoquinoline can appear brownish, as is typical for nitrogen heterocycles. Isoquinoline crystallizes in platelets that have a low solubility in water but dissolve well in ethanol, acetone, diethyl ether, carbon disulfide, and other common organic solvents. Isoquinoline was first isolated from coal tar in 1885. Isoquinoline is a weakly basic compound and it protonates easily to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3. Industrially, isoquinolines are used in the manufacture of dyes, paints, insecticides and antifungals. Isoquinoline is also used as a solvent for the extraction of resins and terpenes, and as a corrosion inhibitor. Isoquinoline also occurs naturally in a number of foods including milk and bonito fish. The Isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. They represent the largest single group of plant alkaloids, and there is great variation in their chemical structures. Some of the important isoquinoline subgroups are the benzyl isoquinolines represented by papaverine and tubocurarine, the benzophenanthridines represented by sanguinarine, the pthalideisoquinolines that contain a gamma-lactone ring and are represented by hydrastine, the morphinans represented by the opium alkaloids (codeine, morphine, thebaine), the protoberberines represented by berberine, and those with the mertine skeleton. Isoquinoline is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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)MeSH, HMDB
Isoquinoline hydrobromideMeSH, HMDB
Isoquinoline hydrochlorideMeSH, HMDB
Isoquinoline hydroiodideMeSH, HMDB
Isoquinoline conjugate acidMeSH, HMDB
Chemical FormulaC9H7N
Average Molecular Weight129.16
Monoisotopic Molecular Weight129.0578
IUPAC Nameisoquinoline
Traditional Nameisoquinoline
CAS Registry Number119-65-3
SMILES
C1=CC=C2C=NC=CC2=C1
InChI Identifier
InChI=1S/C9H7N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-7H
InChI KeyAWJUIBRHMBBTKR-UHFFFAOYSA-N
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point25.5 - 26 °CNot Available
Boiling Point242 °CWikipedia
Water Solubility4.52 mg/mL at 25 °CNot Available
logP2.08Not Available
Predicted Properties
PropertyValueSource
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
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
Predicted GC-MSIsoquinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-fe8f7e7494fe51834c732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-53932d6a797b58065acf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-3bd6daf754e7fa1a62232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0fb9-7900000000-c5e6dca63fceb0eb257a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-a4927588bd0391d5e7682017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-ff5386241f0e22483b362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-43576b7775a986b95c7e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ba509566033d258bb642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a52113b66ca5a059f4972017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-1631e63f0b49a16871502017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0f89-0900000000-95ee1aa2d6255c9ec9362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0ugi-4900000000-1dd979c3c8f2435edd6d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9800000000-d91870148f53fbc1391a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-bca894ecef9e1b2fb95e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-87133a5da2b971403b8c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-87133a5da2b971403b8c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-aa2de101cd67d3fcfd392017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-d3baf54cc19e70a1ec072016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f58afd1811d8a3a4d0d72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-1900000000-4a2becbb485199b25f492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-b4be2f7dd0aed898ee512016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-b2a468601694a7ca84be2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-416ad6650d560fd353182016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034244
DrugBank IDDB04329
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012557
KNApSAcK IDC00055955
Chemspider ID8098
KEGG Compound IDC06323
BioCyc IDISOQUINOLINE
BiGG IDNot Available
Wikipedia LinkIsoquinoline
METLIN IDNot Available
PubChem Compound8405
PDB IDISQ
ChEBI ID16092
References
General References
  1. 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 ]