Harmine (CHEM024335)

Record Information
Version1.0
Creation Date2016-05-25 21:38:26 UTC
Update Date2026-08-18 22:57:48 UTC
Accession NumberCHEM024335
Identification
Common NameHarmine
ClassSmall Molecule
Description
A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.
Contaminant Sources
  • FooDB Chemicals
Contaminant Type
  • Human Neurotoxin
  • PFAS
  • Phytotoxin
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6-MethoxyharmanChEBI
7-Methoxy-1-methyl-9H-beta-carbolineChEBI
BanisterineChEBI
LeucoharmineChEBI
TelepathineChEBI
YageineChEBI
YajeineChEBI
7-Methoxy-1-methyl-9H-b-carbolineGenerator
7-Methoxy-1-methyl-9H-β-carbolineGenerator
1-Methyl-7-methoxy-beta -carbolineHMDB
1-Methyl-7-methoxy-beta-carbolineHMDB
442-51-3 (FREE base)HMDB
7-Methoxy-1-methyl-9H-pyrido(3,4-b)indoleHMDB
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indoleHMDB
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole, 9ciHMDB
BanisterinHMDB
GarminHMDB
HarminHMDB
Harmin hydrochlorideHMDB
HRMHMDB
TelepathienHMDB
TelepathinHMDB
YageinHMDB
Chemical FormulaC13H12N2O
Average Molecular Mass212.247 g/mol
Monoisotopic Mass212.095 g/mol
CAS Registry Number442-51-3
IUPAC Name7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
Traditional Nameharmine
SMILESCOC1=CC=C2C(NC3=C2C=CN=C3C)=C1
InChI IdentifierInChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
InChI KeyBXNJHAXVSOCGBA-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
  • Anisole
  • Methylpyridine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.061 g/LALOGPS
logP3.05ALOGPS
logP1.85ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)6.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.91 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.37 m³·mol⁻¹ChemAxon
Polarizability23.45 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
External Links
DrugBank IDDB07919
HMDB IDHMDB0030311
FooDB IDFDB002149
Phenol Explorer IDNot Available
KNApSAcK IDC00001737
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDHRM
Wikipedia LinkHarmine
Chemspider ID4444445
ChEBI ID28121
PubChem Compound ID5280953
Kegg Compound IDC06538
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11473435
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22877698
3. Gambelunghe C, Aroni K, Rossi R, Moretti L, Bacci M: Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage. Biomed Chromatogr. 2008 Oct;22(10):1056-9. doi: 10.1002/bmc.1023.
4. Yonezawa T, Lee JW, Hibino A, Asai M, Hojo H, Cha BY, Teruya T, Nagai K, Chung UI, Yagasaki K, Woo JT: Harmine promotes osteoblast differentiation through bone morphogenetic protein signaling. Biochem Biophys Res Commun. 2011 Jun 3;409(2):260-5. doi: 10.1016/j.bbrc.2011.05.001. Epub 2011 May 6.
5. Hamsa TP, Kuttan G: Harmine inhibits tumour specific neo-vessel formation by regulating VEGF, MMP, TIMP and pro-inflammatory mediators both in vivo and in vitro. Eur J Pharmacol. 2010 Dec 15;649(1-3):64-73. doi: 10.1016/j.ejphar.2010.09.010. Epub 2010 Sep 19.
6. Reus GZ, Stringari RB, de Souza B, Petronilho F, Dal-Pizzol F, Hallak JE, Zuardi AW, Crippa JA, Quevedo J: Harmine and imipramine promote antioxidant activities in prefrontal cortex and hippocampus. Oxid Med Cell Longev. 2010 Sep-Oct;3(5):325-31. Epub 2010 Sep 1.
7. Carpentier RG: The effect of harmine on the action potential of the guinea-pig atrial muscle depends on the external calcium concentration. Br J Pharmacol. 1981 Oct;74(2):415-8.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.