Tetrahydroharmine (THH)

Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi. THH weakly inhibits serotonin reuptake. Two other harmala alkaloids in B. caapi, harmaline and harmine, are reversible inhibitors of monoamine oxidase A. Tetrahydroharmine, however, does not inhibit monoamine oxidase A. N,N-Dimethyltryptamine (DMT), harmine, harmaline and tetrahydroharmine (THH) are the characteristic alkaloids found in Amazonian sacraments known as hoasca, ayahuasca, and yajè. Such beverages are characterized by the presence of these three harmala alkaloids, where harmine and harmaline reversibly inhibit monoamine oxidase A (MAO-A) while tetrahydroharmine weakly inhibits the uptake of serotonin. Together, both actions increase central and peripheral serotonergic activity while facilitating the psychoactivity of DMT.