5methoxytryptamine

5-Methoxytryptamine (5-MT) is a substituted tryptamine with the chemical formula C11H12N2O. It consists of an indole ring, a methoxy group at the 5‑position of the ring, and an ethylamine side chain attached to the nitrogen of the indole. The compound is a derivative of tryptamine and is related structurally to serotonergic agents such as psilocin and DOI.

The synthesis of 5-MT typically involves the alkylation of 5‑hydroxytryptamine with a methyl donor, followed by N‑ethylation. In laboratory settings, 5‑MT can be produced by methylating 5‑hydroxytryptophan to 5‑methoxytryptamine through reductive amination of the carboxyl group to an ethylamine.

Pharmacologically, 5-MT is a partial agonist at serotonin (5‑HT) receptors, with a marked affinity for 5‑HT1A and 5‑HT2A receptors. It exhibits central nervous system activity but is considerably less potent than its analogues such as 5‑MT‑DMT. In vitro studies show moderate affinity for 5‑HT2A receptors with an IC₅₀ around 3–5 µM, while its affinity for 5‑HT1A is lower. 5‑MT does not inhibit the reuptake of serotonin nor does it inhibit monoamine oxidase significantly at low concentrations.

Legal status varies by country. In the United States, 5‑MT is not specifically scheduled, but analog laws could apply if it is considered an analog of a controlled substance. In the United Kingdom it falls under the Psychoactive Substances Act, rendering its sale or distribution illegal. Other jurisdictions may classify it analogously to other tryptamines.

Uses of 5-MT are largely restricted to research. Its moderate hallucinogenic properties have led to limited exploration in psychopharmacology and receptor-binding studies. The compound has not been reported for recreational use and is rarely encountered outside specialized laboratory contexts.

References to further reading can be found in peer‑reviewed pharmacological literature, including studies on tryptamine receptor affinity and behavioral effects in rodent models.