This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Harmaline
Accession Number
DB13875
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Harmaline hydrochloride64056X913V363-11-1PULNGKOFHCQQQA-UHFFFAOYSA-N
Harmaline hydrochloride dihydrate5B4DGH2M9R6027-98-1LCEKUHFBUFUSSY-UHFFFAOYSA-N
Categories
UNII
CN58I4TOET
CAS number
304-21-2
Weight
Average: 214.2631
Monoisotopic: 214.11061308
Chemical Formula
C13H14N2O
InChI Key
RERZNCLIYCABFS-UHFFFAOYSA-N
InChI
InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3
IUPAC Name
7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole
SMILES
COC1=CC2=C(C=C1)C1=C(N2)C(C)=NCC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHistamine N-methyltransferase
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Harmaline is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Harmaline is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Harmaline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Harmaline.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Harmaline is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with Harmaline.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Harmaline.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Harmaline is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineHarmaline may increase the hypertensive activities of 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Harmaline.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0030310
KEGG Compound
C06536
PubChem Compound
5280951
PubChem Substance
347829327
ChemSpider
10211258
BindingDB
50029799
ChEBI
28172
ChEMBL
CHEMBL340807
Wikipedia
Harmaline

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0576 mg/mLALOGPS
logP2.61ALOGPS
logP1.67ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.95ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.15 m3·mol-1ChemAxon
Polarizability24.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-2920000000-44473ef3fbb78c164b21

Taxonomy

Description
This compound belongs to the class of organic compounds known as harmala alkaloids. These 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Harmala alkaloids
Sub Class
Not Available
Direct Parent
Harmala alkaloids
Alternative Parents
Beta carbolines / 3-alkylindoles / Anisoles / Alkyl aryl ethers / Pyrroles / Heteroaromatic compounds / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds
show 1 more
Substituents
Harmaline / Harman / Beta-carboline / Pyridoindole / 3-alkylindole / Indole or derivatives / Indole / Anisole / Alkyl aryl ether / Benzenoid
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
harmala alkaloid (CHEBI:28172) / Indole alkaloids (C06536) / an alkaloid (CPD-9939)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Histamine n-methyltransferase activity
Specific Function
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name
HNMT
Uniprot ID
P50135
Uniprot Name
Histamine N-methyltransferase
Molecular Weight
33294.765 Da
References
  1. Cumming P, Vincent SR: Inhibition of histamine-N-methyltransferase (HNMT) by fragments of 9-amino-1,2,3,4-tetrahydroacridine (tacrine) and by beta-carbolines. Biochem Pharmacol. 1992 Sep 1;44(5):989-92. [PubMed:1530666]

Drug created on August 02, 2017 13:23 / Updated on October 16, 2018 08:47