Record Information
Version1.0
Creation date2010-04-08 22:04:49 UTC
Update date2020-02-24 19:10:18 UTC
Primary IDFDB001053
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHarmalol
DescriptionAlkaloid from Passiflora incarnata (maypops) Harmaline is a reversible inhibitor of MAO-A (RIMA).; Harmine is a reversible inhibitor of MAO-A (RIMA).; It is important to note that unlike synthetic pharmaceutical MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors.; Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala (also known as Harmal or Syrian Rue), including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine which was once known as Telepathine and Banisterine is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi, but not P. harmala. Dr. Alexander Shulgin has suggesed that harmaline may be a breakdown product of harmine. Harmine and harmaline are reversible MAOIs of the MAO-A isoform of the enzyme, and can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.; The harmala alkaloids occur in Peganum harmala in concentrations of roughly 3%, though tests have documented anywhere from 2-7%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43% for harmine, 0.03-0.83% for harmaline and 0.05-2.94% for tetrahydroharmine. Other psychoactive plants are often added to Ayahuasca to achieve visionary states of consciousness; for example leaves from Psychotria viridis, which is a source of dimethyltryptamine (DMT). The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract. The harmala alkaloids are not especially psychoactive on their own, even at high dosages, when vomiting and diarrhea become the main effect.
CAS Number525-57-5
Structure
Thumb
Synonyms
SynonymSource
1-Methyl-4,9-dihydro-3H-beta-carbolin-7-olChEBI
HarmidolChEBI
HarmololChEBI
1-Methyl-4,9-dihydro-3H-b-carbolin-7-olGenerator
1-Methyl-4,9-dihydro-3H-β-carbolin-7-olGenerator
1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol hydrochlorideHMDB
3,4-Dihydro-1-methyl-2H-pyrido[3,4-b]indol-7-olHMDB
3,4-Dihydro-7-hydroxy-1-methyl-b-carbolineHMDB
4,9-Dihydro-1-methyl-3H-pyrido(3,4-b)indol-7-olHMDB
4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-olHMDB
4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol, 9ciHMDB
Harmalol hydrochlorideMeSH
Harmalol hydrochloride, dihydrateMeSH
Harmalol trihydrateMeSH
Harmalol lactate, dihydrateMeSH
Harmalol dihydrochlorideMeSH
2H-Pyrido[3,4-b]indol-7-ol, 3,4-dihydro-1-methyl-biospider
3,4-dihydro-1-Methyl-2H-pyrido[3,4-b]indol-7-olHMDB
3H-Pyrido[3,4-b]indol-7-ol, 4,9-dihydro-1-methyl-biospider
4,9-dihydro-1-Methyl-3H-pyrido[3,4-b]indol-7-olHMDB
4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indol-7-ol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.94ALOGPS
logP1.52ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.61ChemAxon
pKa (Strongest Basic)6.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.38 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity59.67 m³·mol⁻¹ChemAxon
Polarizability22.08 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H12N2O
IUPAC name1-methyl-3H,4H,9H-pyrido[3,4-b]indol-7-ol
InChI IdentifierInChI=1S/C12H12N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6,14-15H,4-5H2,1H3
InChI KeyRHVPEFQDYMMNSY-UHFFFAOYSA-N
Isomeric SMILESCC1=NCCC2=C1NC1=C2C=CC(O)=C1
Average Molecular Weight200.2365
Monoisotopic Molecular Weight200.094963016
Classification
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
  • Harmaline
  • Harmalol
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.98%; H 6.04%; N 13.99%; O 7.99%DFC
Melting PointMp 100-105°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP2.19HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data376 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-0900000000-e4464398b4dec3fc7352JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7190000000-1284b3e28670778298feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0290000000-a117734dd274e28b35adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1970000000-b19698ef3a7ac01eec3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-0900000000-f10b93cb6c00a71896feJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-aaba7e72d490321c1aa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-78586bb5e1894bd774f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-2900000000-fd7e4b643b65563440d4JSpectraViewer
ChemSpider ID11262879
ChEMBL IDCHEMBL129177
KEGG Compound IDC06537
Pubchem Compound ID5353656
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29838
CRC / DFC (Dictionary of Food Compounds) IDBQW40-I:BQW40-I
EAFUS IDNot Available
Dr. Duke IDHARMALOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHarmalol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti mitoticDUKE
aphrodisiacDUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
desmutagenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).