Harmine

Names

IUPAC names

7-MeO-1-Me-9H
-pyrido[3,4-b]-indole

Identifiers

CAS Number

442-51-3^Y

3D model (Jmol)

CHEBI:28121^Y

ChEMBL269538^Y

4444445^Y

DB07919^Y

C06538^Y

4FHH5G48T7^Y

InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3^Y

Key: BXNJHAXVSOCGBA-UHFFFAOYSA-N^Y
InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3

Key: BXNJHAXVSOCGBA-UHFFFAOYAR

SMILES

n3ccc2c1c(cc(OC)cc1)nc2c3C

Properties

Chemical formula

C₁₃H₁₂N₂O

Molar mass

212.25 g/mol

Melting point

321 °C (610 °F; 594 K) (·HCl); 262 °C (·HCl·2H₂O)

Solubility in water

insoluble

Solubility in Dimethyl sulfoxide

100mM

Solubility in Ethanol

1 mg/mL

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(what is ^YN ?)

Infobox references

Harmine, also known as telepathine, is a fluorescent harmala alkaloid belonging to the beta-carboline family of compounds. It occurs in a number of different plants, most notably the Middle Eastern plant harmal or Syrian rue (Peganum harmala) and the South American vine Banisteriopsis caapi (also known as "yage" or "ayahuasca"). Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a RIMA. Harmine selectively binds to MAO-A but does not inhibit the variant MAO-B.

Isolated from the plant Peganum harmala, harmine is an indole alkaloid with the pyrido[3,4-b]indole ring structure that is characteristic of the β-carboline alkaloids. The β-carboline alkaloids include harmine, harmaline, harman and harmalol. These molecules are heterocyclic amines, biosynthesized through the combination of five- and six-membered ring structures that are derived from an amino acid- either L-tryptophan or tryptamine- which facilitates the formation of an indole ring system.

The coincident occurrence of β-carboline alkaloids and serotonin in P. harmala indicates the presence of two very similar, interrelated biosynthetic pathways, which makes it difficult to definitively identify whether free tryptamine or L-tryptophan is the precursor to the biosynthesis of harmine. However, it is postulated that L-tryptophan is the most likely precursor, with tryptamine existing as an intermediate in the pathway.

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