Showing Compound Card for Harman (CDB005369)

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Record Information
Version1.0
Created at2020-04-27 16:13:45 UTC
Updated at2021-01-04 20:37:40 UTC
CannabisDB IDCDB005369
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHarman
DescriptionHarman, or 3-methyl-4-carboline, 1-methyl-9H-pyrido(3,4-b)indole, also known as aribin or locuturin, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-beta]indole. Harman is an indole alkaloid with a 9H-beta-carboline backbone carrying a methyl substituent at C-1. Harman is a strong basic compound, that is moderately soluble in water and has a bitter taste. Harman is found in highest concentrations in passion fruits, passion leaves and has also been detected in chicories, wild apricot, and saffrons. Harman is found in many baked goods like bread, toasted bread, cereals, as well as coffee, coffee derivatives, maize, barley, soy and cooked meat and fish. This could make harman a potential biomarker for the consumption of these foods. Harman is a neuroactive beta-carboline and is a specific, reversible inhibitor of monoamine oxidase A(MAO-A) (PMID: 6255348 ). As abnormal MAO-A activity has been associated with depression, Parkingson’s Disease and Alzheimer’s disease, inhibition of MAO-A activity by harman may alleviate these conditions. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, the flowering plants-Passiflora incarnata, Peganum harmala, the hallucinogenic plants-Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke (PMID: 30978920). Harman is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Methyl-2-carbolineChEBI
1-Methyl-9H-beta-carbolineChEBI
1-Methyl-beta-carbolineChEBI
1-MethylnorharmanChEBI
AribinChEBI
AribineChEBI
HarmaneChEBI
L-MethylpyridobindoleChEBI
LocuturinChEBI
LocuturineChEBI
LoturineChEBI
PassiflorinChEBI
1-Methyl-9H-b-carbolineGenerator
1-Methyl-9H-β-carbolineGenerator
1-Methyl-b-carbolineGenerator
1-Methyl-β-carbolineGenerator
1-Methyl-9H-pyrido[3,4-b]indoleHMDB
1-Methyl-9H-pyrido[3,4-b]indole, 9ciHMDB
2-Methyl-beta-carbolineHMDB
3-Methyl-4-carbolineHMDB
L-Methyl-pyridobindoleHMDB
PassiflorineHMDB
ZygofabagineHMDB
Harman hydrochlorideHMDB
Chemical FormulaC12H10N2
Average Molecular Weight182.22
Monoisotopic Molecular Weight182.0844
IUPAC Name1-methyl-9H-pyrido[3,4-b]indole
Traditional Nameharmane
CAS Registry Number486-84-0
SMILES
CC1=C2NC3=CC=CC=C3C2=CC=N1
InChI Identifier
InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
InChI KeyPSFDQSOCUJVVGF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassHarmala alkaloids
Sub ClassNot Available
Direct ParentHarmala alkaloids
Alternative Parents
Substituents
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Indole
  • Indole or derivatives
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point237 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP3.10Not Available
Predicted Properties
PropertyValueSource
logP3.36ALOGPS
logP2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.72ChemAxon
pKa (Strongest Basic)5.97ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.91 m³·mol⁻¹ChemAxon
Polarizability20.28 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHarman, non-derivatized, GC-MS Spectrumsplash10-001i-4900000000-2caa4dc9ec4e3750fe94Spectrum
GC-MSHarman, non-derivatized, GC-MS Spectrumsplash10-001i-4900000000-2caa4dc9ec4e3750fe94Spectrum
Predicted GC-MSHarman, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f89-0900000000-1eb823770f43aa96d079Spectrum
Predicted GC-MSHarman, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-8a722b1b5d7b5941896b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-c3e22e3a50c1a33d33132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0900000000-da3abe12c596a25c4fc72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00lr-0900000000-a0630fe37a9dae9007112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-fe40ad28de7c40fde9732017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-2c091f7fb293a57028072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-37a11b66e75cedf3e0722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-2900000000-753e83180abd8e8f43062017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-053r-4900000000-a0c45efe16d695cf04652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-2900000000-4e2e84a5d7cb4f3b6e5a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , negativesplash10-001i-0900000000-da5f8f71b14a2afaf96b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-b61926dd87fa8a8bf5472017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-be2b3d6251e5698ec1842017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-2467a87546dc5758f74c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-6222b796373c7d683edd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-5f9fc354bf2eb82f440c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-8f767ae14c8cb390abd42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-3206fb22991bbadfb4102017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-fbe37bd173c6820a5fbf2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-f0389c36d5ddc1a056cd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-f4d0d496031eda8facca2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-0900000000-24a22633d62b61cf09b22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-c6d6c9589b7c3045e05e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-155dea2165739f0af46e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067i-0900000000-78073f143aded0ccce812016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0035196
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021482
KNApSAcK IDC00001736
Chemspider ID4444755
KEGG Compound IDC09209
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHarman
METLIN IDNot Available
PubChem Compound5281404
PDB IDNot Available
ChEBI ID5623
References
General References
  1. Rommelspacher H, Nanz C, Borbe HO, Fehske KJ, Muller WE, Wollert U: 1-Methyl-beta-carboline (harmane), a potent endogenous inhibitor of benzodiazepine receptor binding. Naunyn Schmiedebergs Arch Pharmacol. 1980 Oct;314(1):97-100. doi: 10.1007/BF00498436. [PubMed:6255348 ]