harmine
Sign in to saveAlso known as 7-methoxy-1-methyl-9H-beta-carboline, 6-methoxyharman, yageine, banisterine, yajeine, leucoharmine, telepathine
Harmine, also known as banisterine or telepathine, as well as 7-methoxyharman or 7-methoxy-1-methyl-β-carboline, is a β-carboline and a harmala alkaloid which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It occurs in a number of different plants, most notably Peganum harmala and Banisteriopsis caapi. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B.
Key facts
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 443852670
- Drug.image
- Harmine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225px
- Drug.image2
- Harmine_3d_structure.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 225px
- Drug.routes_of_administration
- Oral, sublingual, subcutaneous injection, intramuscular injection, intravenous injection
- Drug.class
- Hallucinogen; Oneirogen; Monoamine oxidase inhibitor; Reversible inhibitor of MAO-A
- Drug.ATC_prefix
- None
- Drug.onset
- Unknown
- Drug.elimination_half life
- 1.3–1.9 hours (1–3 hours)
- Drug.duration_of_action
- Oral: 6–8 hours: 3–5 hours: 30–45 minutes
- Drug.CAS_number
- 442-51-3
- Drug.PubChem
- 5280953
- Drug.DrugBank
- DB07919
- Drug.ChemSpiderID
- 4444445
via Wikipedia infobox
Research
1,503 papersvia PubMed
Wikidata facts
- Mass
- 212.095
Show 6 more facts
- canonical SMILES
- CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC
- chemical formula
- C₁₃H₁₂N₂O
- melting point
- 273
- Commons category
- Harmine
- decomposition point
- 261
- pKa
- 7.70
via Wikidata · CC0
~17 min read
Article
23 sectionsContents
- Use and effects
- Hallucinogen
- Monoamine oxidase inhibitor
- Other uses
- Adverse effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Synthesis
- Natural occurrence
- Biosynthesis
- History
- Society and culture
- Names
- Legal status
- Australia
- Canada
- Research
- Pancreatic islet cell proliferation
- See also
- References
- External links
Harmine, also known as banisterine or telepathine, as well as 7-methoxyharman or 7-methoxy-1-methyl-β-carboline, is a β-carboline and a harmala alkaloid which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It occurs in a number of different plants, most notably Peganum harmala and Banisteriopsis caapi. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B.
Harmine is found in various plants—including tobacco, Passiflora species, lemon balm, and several Banisteriopsis species—as well as in some butterflies of the Nymphalidae family. It was first isolated and named by German chemist Julius Fritzsche in 1847 from Peganum harmala seeds, later identified in Banisteriopsis caapi under various names, with its structure determined in 1927.