Structure via PubChem · Public domain (PubChem)
harmaline
Sign in to saveAlso known as 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a harmala alkaloid and β-carboline which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It is the partly hydrogenated form of harmine.
Chemical data
- Formula
- C13H14N2O
- Molecular weight
- 214.26 g/mol
- IUPAC name
- 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
- SMILES
- CC1=NCCC2=C1NC3=C2C=CC(=C3)OC
- InChIKey
- RERZNCLIYCABFS-UHFFFAOYSA-N
- XLogP
- 2.1
- Polar surface area
- 37.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,051 papers- Evaluation of therapeutic role of harmaline: in vitro cytotoxicity targeting nucleic acids.Journal of Asian natural products research · 2024
- Harmaline toxicity on dorsal striatal neurons and its role in tremor.Neurotoxicology · 2023
- Harmaline induces apoptosis and inhibits migration in A2780 ovarian cancer cells in vitro.Physiological reports · 2024
- Considerations Using Harmaline for a Primate Model of Tremor.Tremor and other hyperkinetic movements (New York, N.Y.) · 2021
- Harmaline exerts potentially anti-cancer effects on U-87 human malignant glioblastoma cells in vitro.Molecular biology reports · 2023
via PubMed
Wikidata facts
- Has part
- oxygen
- Mass
- 214.110613068
Show 6 more facts
- canonical SMILES
- N1=C(C=2NC=3C=C(OC)C=CC3C2CC1)C
- chemical formula
- C₁₃H₁₄N₂O
- subject has role
- monoamine oxidase inhibitor
- Commons category
- Harmaline
- melting point
- 230
- pKa
- 4.2
via Wikidata · CC0
~9 min read
Encyclopedic overview
20 sectionsContents
- Use and effects
- As a hallucinogen
- As an MAOI
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Properties
- Synthesis
- Analogues
- Natural occurrence
- History
- Society and culture
- Legal status
- Australia
- Canada
- See also
- References
- External links
Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a harmala alkaloid and β-carboline which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It is the partly hydrogenated form of harmine.
Plants containing harmaline are combined in ayahuasca to inhibit monoamine oxidase, allowing orally consumed dimethyltryptamine (DMT) to become orally active and produce psychoactive effects. Harmala alkaloids, including harmaline, are psychoactive on their own in humans, with harmaline being particularly hallucinogenic, although other compounds such as harmine and tetrahydroharmine have also been reported to produce hallucinogenic effects as well.
Excerpted from Wikipedia’s “harmaline” article, available under the CC BY-SA 4.0 licence.