Tetrahydroharmol (CHEM023472)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:04:58 UTC
Update Date2016-11-09 01:17:43 UTC
Accession NumberCHEM023472
Identification
Common NameTetrahydroharmol
ClassSmall Molecule
DescriptionTetrahydroharmol is found in fruits. Tetrahydroharmol is an alkaloid from Elaeagnus angustifolia (Russian olive) 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
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3,4-Tetrahydro-7-hydroxy-1-methyl-b-carbolineHMDB
2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indol-7-ol, 8ciHMDB
Tetrahydroharmalol hydrochlorideHMDB
Tetrahydroharmol hydrochlorideHMDB
Chemical FormulaC12H14N2O
Average Molecular Mass202.252 g/mol
Monoisotopic Mass202.111 g/mol
CAS Registry Number17952-75-9
IUPAC Name1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol
Traditional Name1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol
SMILESCC1NCCC2=C1NC1=C2C=CC(O)=C1
InChI IdentifierInChI=1S/C12H14N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6-7,13-15H,4-5H2,1H3
InChI KeyAZTMWIPCEFFOJD-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
  • Harmaline
  • Harmalol
  • Harman
  • Beta-carboline
  • Pyridoindole
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Organoheterocyclic compound
  • Azacycle
  • Secondary aliphatic amine
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
logP1.58ALOGPS
logP1.24ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area48.05 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity59.98 m³·mol⁻¹ChemAxon
Polarizability22.71 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-059i-0910000000-70bfd23f847e808c0f3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-3690000000-b50240f2dfd89efd370aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-dbf0ba828934a3d16b85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-1950000000-cd07495fb3fab4274fb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-0900000000-a9ba3cd5545cb553e8b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-54e3ee3f4a7697515db6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-ffda0c873192bf93a9c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ac9-2900000000-8947f0a5c18fbf6a5813Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-53c3fa4c5460be246d0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-53c3fa4c5460be246d0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053s-0900000000-a644d6e5d295344f8a9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-ee2fb06e46c3edc2e07aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0190000000-85a10545fbc1fd164f55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-2900000000-4bc929863d4e520a914dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029835
FooDB IDFDB001050
Phenol Explorer IDNot Available
KNApSAcK IDC00057972
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetrahydroharmol
Chemspider ID327573
ChEBI ID114202
PubChem Compound ID368982
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.