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

Identification

Generic Name
Harmaline
DrugBank Accession Number
DB13875
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 214.2631
Monoisotopic: 214.11061308
Chemical Formula
C13H14N2O
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHistamine N-methyltransferase
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

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Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Harmaline.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Harmaline is combined with Abciximab.
AcarboseHarmaline may increase the hypoglycemic activities of Acarbose.
AcebutololHarmaline may increase the hypotensive activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Harmaline.
AcemetacinThe risk or severity of hypertension can be increased when Acemetacin is combined with Harmaline.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Harmaline is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Harmaline.
AcetohexamideHarmaline may increase the hypoglycemic activities of Acetohexamide.
AcetophenazineThe risk or severity of extrapyramidal symptoms can be increased when Harmaline is combined with Acetophenazine.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Harmaline hydrochloride64056X913V363-11-1PULNGKOFHCQQQA-UHFFFAOYSA-N
Harmaline hydrochloride dihydrate5B4DGH2M9R6027-98-1LCEKUHFBUFUSSY-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
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Substituents
3-alkylindole / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-carboline / Ether / Harmaline / Harman
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
harmala alkaloid (CHEBI:28172) / Indole alkaloids (C06536) / an alkaloid (CPD-9939)
Affected organisms
Not Available

Chemical Identifiers

UNII
CN58I4TOET
CAS number
304-21-2
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

References

General References
Not Available
Human Metabolome Database
HMDB0030310
KEGG Compound
C06536
PubChem Compound
5280951
PubChem Substance
347829327
ChemSpider
10211258
BindingDB
50029799
ChEBI
28172
ChEMBL
CHEMBL340807
ZINC
ZINC000100014157
Wikipedia
Harmaline

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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. [Article]

Drug created at August 02, 2017 19:23 / Updated at October 26, 2021 20:02