Showing Compound Card for 1-Methyl-4,9-dihydro-3H-beta-carboline (CDB005737)

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Record Information
Version1.0
Created at2020-04-27 16:50:42 UTC
Updated at2021-01-04 18:59:24 UTC
CannabisDB IDCDB005737
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Methyl-4,9-dihydro-3H-beta-carboline
DescriptionHarmalan also known as harmalane, dihydroharman or 1-Methyl-4,9-dihydro-3H-beta-carboline is a methylated derivative of 4,9-dihydro-3H-beta-carboline. It 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. Harmalan is also classified as a beta-carboline alkaloid. Harmala alkaloids apper to act as a monoamine oxidase (MAO) inhibitors. Harmalan is presumably formed in vivo as an intermediate product of the biosynthesis of harman as well as tetrahydroharman in certain plants such as Peganum harmala and many other plants, such as passion flower (PMID: 2580722 ). Harmalan is also found in mammals, however it is not clear how it is produced. Harmalan is one of the active components of clonidine-displacing substance (CDS) (PMID: 15610033 ). CDS was initially recognized as an endogenous, small molecule substance that regulated insulin secretion by acting through the binding of the pancreatic islet beta-cell imidazoline site (or I-site), a nonadrenoceptor recognition site (PMID: 9792210 ). Harmalan has high (nanomolar) affinity for both type 1 and type 2 imidazoline binding sites. Imidazoline receptors are the primary receptors on which clonidine and other imidazolines act. There are three main classes of imidazoline receptor: I1 is involved in inhibition of the sympathetic nervous system to lower blood pressure, I2 has as yet uncertain functions but is implicated in several psychiatric conditions and I3 regulates insulin secretion. Another well-known CDS is agmatine (PMID: 7906055 ). Harmalan is thought to have anti-diabetic properties. Ethanolic extracts of Paganum harmala (which presumably contain Harmalan) have been shown to be as effective as metformin in reducing the blood glucose levels of normoglycemic and streptozotocin-induced diabetic rats (PMID: 23105794 ). Harmalan has also been shown to exhibit antifungal and antiviral activities (PMID: 24460429 ). Harmalan is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Methyl-3,4-dihydro-beta-carbolineHMDB
1-Methyl-4,9-dihydro-3H-beta-carbolineHMDB
3,4-Dihydro-1-methyl-2H-pyrido[3,4-b]indoleHMDB
4,9-Dihydro-1-methyl-3H-pyrido(3,4-b)indoleHMDB
4,9-Dihydro-1-methyl-3H-pyrido[3,4-b]indole, 9ciHMDB
DihydroharmanHMDB
Chemical FormulaC12H12N2
Average Molecular Weight184.24
Monoisotopic Molecular Weight184.1
IUPAC Name1-methyl-3H,4H,9H-pyrido[3,4-b]indole
Traditional Name1-methyl-3H,4H,9H-pyrido[3,4-b]indole
CAS Registry Number525-41-7
SMILES
CC1=NCCC2=C1NC1=CC=CC=C21
InChI Identifier
InChI=1S/C12H12N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-5,14H,6-7H2,1H3
InChI KeyCWOYLIJQLSNRRN-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
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ketimine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Imine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.64ALOGPS
logP1.83ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)15.04ChemAxon
pKa (Strongest Basic)8.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity57.69 m³·mol⁻¹ChemAxon
Polarizability21.01 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1-Methyl-4,9-dihydro-3H-beta-carboline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0aou-0900000000-f4e44830fc68268ca1d4Spectrum
Predicted GC-MS1-Methyl-4,9-dihydro-3H-beta-carboline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00kf-0900000000-cac9e8af853ce6d05f912017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00kf-0900000000-cac9e8af853ce6d05f912017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c2f098f419ec8b43341a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-0f35bce7fc33f4f2d24a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-b6f1364180703f74b0432016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-5b807ce1861cae768c7b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-f78325499d14762d4fff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vl-2900000000-bfbe18f400c46178f3a42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-8d15c8b43a2a4b2520b42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-8d15c8b43a2a4b2520b42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lu-0900000000-23cb6182b1f2e7d5f88e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-841022a695ed338266912021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f5ea68ba19a0a333dce02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-2900000000-18a09d2aeb50b46cb5732021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029834
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001049
KNApSAcK IDC00054103
Chemspider ID10309487
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound160510
PDB IDNot Available
ChEBI ID168990
References
General References
  1. Rommelspacher H, Bruning G, Susilo R, Nick M, Hill R: Pharmacology of harmalan (1-methyl-3,4-dihydro-beta-carboline). Eur J Pharmacol. 1985 Mar 12;109(3):363-71. doi: 10.1016/0014-2999(85)90397-8. [PubMed:2580722 ]
  2. Parker CA, Anderson NJ, Robinson ES, Price R, Tyacke RJ, Husbands SM, Dillon MP, Eglen RM, Hudson AL, Nutt DJ, Crump MP, Crosby J: Harmane and harmalan are bioactive components of classical clonidine-displacing substance. Biochemistry. 2004 Dec 28;43(51):16385-92. doi: 10.1021/bi048584v. [PubMed:15610033 ]
  3. Chan SL: Clonidine-displacing substance and its putative role in control of insulin secretion: a minireview. Gen Pharmacol. 1998 Oct;31(4):525-9. doi: 10.1016/s0306-3623(98)00052-4. [PubMed:9792210 ]
  4. Li G, Regunathan S, Barrow CJ, Eshraghi J, Cooper R, Reis DJ: Agmatine: an endogenous clonidine-displacing substance in the brain. Science. 1994 Feb 18;263(5149):966-9. doi: 10.1126/science.7906055. [PubMed:7906055 ]
  5. Singh AB, Chaturvedi JP, Narender T, Srivastava AK: Preliminary studies on the hypoglycemic effect of Peganum harmala L. Seeds ethanol extract on normal and streptozotocin induced diabetic rats. Indian J Clin Biochem. 2008 Oct;23(4):391-3. doi: 10.1007/s12291-008-0086-3. Epub 2008 Dec 20. [PubMed:23105794 ]
  6. Song H, Liu Y, Liu Y, Wang L, Wang Q: Synthesis and antiviral and fungicidal activity evaluation of beta-carboline, dihydro-beta-carboline, tetrahydro-beta-carboline alkaloids, and their derivatives. J Agric Food Chem. 2014 Feb 5;62(5):1010-8. doi: 10.1021/jf404840x. Epub 2014 Jan 24. [PubMed:24460429 ]