← DISCOVERY / BETA CARBOLINE

Tetrahydroharmine

THH

Third major beta-carboline of Banisteriopsis caapi (alongside harmine and harmaline). A weaker MAO-A inhibitor but a serotonin reuptake inhibitor in its own right — believed to be a major contributor to the long, dreamy afterglow of an ayahuasca session.

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Structure · PubChem (NCBI) Public Domain

THREE-DIMENSIONAL STRUCTURE

The molecule, in space.

Atoms positioned in their lowest-energy 3D geometry, sourced from PubChem. Drag to rotate · pinch or scroll to zoom · switch between stick, sphere, and line representations to feel the shape from different angles.

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3D structure · PubChem CID 442118 · drag to rotate · scroll to zoom

SMILES NOTATION

C[C@@H]1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC

PubChem CID 442118 →

RECEPTOR PROFILE

The pharmacological targets through which this compound exerts its effects.

MAO-A inhibitor (weak)Serotonin reuptake inhibitor

NATURAL SOURCES

Living organisms in which this compound is naturally found.

The primary vine used in traditional ayahuasca brews. Contains powerful beta-carboline MAO inhibitors that allow DMT from other plants to become orally active.

Hardy Old-World shrub whose seeds are extraordinarily rich in the beta-carboline alkaloids harmine, harmaline, and tetrahydroharmine — the same MAO-inhibiting chemistry as Banisteriopsis caapi, making it the cornerstone of so-called 'ayahuasca analogs'.

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REFERENCES

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RELATED MOLECULES

Other beta carbolines

Beta-carboline alkaloid and potent MAO-A inhibitor found in Banisteriopsis caapi. Enables oral activity of DMT in ayahuasca.

Banisteriopsis caapiPeganum harmala

The major beta-carboline alkaloid of Banisteriopsis caapi, and the primary MAO-A inhibitor responsible for making oral DMT active in ayahuasca. Acts as a reversible inhibitor of monoamine oxidase A and is itself mildly psychoactive at higher doses.

Banisteriopsis caapiPeganum harmala

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