NAV

Harmaline

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
Similar Structures
Weight
Average: 214.2631
Monoisotopic: 214.11061308
Chemical Formula
C13H14N2O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with Harmaline.
AbaloparatideHarmaline may increase the orthostatic hypotensive activities of Abaloparatide.
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.
Food Interactions
Not Available

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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
show 1 more
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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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)7.96Chemaxon
Physiological Charge1Chemaxon
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-MSsplash10-006t-0900000000-8b0bbd88d925dd13fd02
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-2920000000-44473ef3fbb78c164b21
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-2920000000-44473ef3fbb78c164b21
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-7e9636e279c80c497c59
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-683593c82dbaf3ba4fb1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-85a0882d4f0d9f880264
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dj-0900000000-8ad76809df09afdb37f9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-1890000000-fe7ae75ada48e3022d89
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01c0-0900000000-35867180f354323cb1d9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.8228655
predicted
DarkChem Lite v0.1.0
[M-H]-157.7708655
predicted
DarkChem Lite v0.1.0
[M-H]-158.0426655
predicted
DarkChem Lite v0.1.0
[M-H]-153.20103
predicted
DeepCCS 1.0 (2019)
[M+H]+159.1569655
predicted
DarkChem Lite v0.1.0
[M+H]+158.4740655
predicted
DarkChem Lite v0.1.0
[M+H]+158.9691655
predicted
DarkChem Lite v0.1.0
[M+H]+155.55904
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.0064655
predicted
DarkChem Lite v0.1.0
[M+Na]+158.3321655
predicted
DarkChem Lite v0.1.0
[M+Na]+161.6522
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histamine N-methyltransferase
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 February 20, 2024 23:31