5-MeO-DMT-d4, also known as ñ,ñ,ò,ò-tetradeutero-5-MeO-DMT, is a serotonin receptor modulator and putative psychedelic drug of the tryptamine and 5-methoxytryptamine families related to 5-MeO-DMT. It is the isotopologue of 5-MeO-DMT in which the hydrogen atoms at the ñ and ò positions have been replaced with the deuterium isotopes.
5-MeO-DMT-d4 shows similar affinities for serotonin receptors and other targets as 5-MeO-DMT. However, the drug is thought to be much more resistant to metabolism by monoamine oxidase (MAO) than 5-MeO-DMT, which in turn may result in greater potency and/or a longer duration. In addition, it may result in the drug becoming orally active, though this remains to be studied. It is known that monoamine oxidase inhibitors (MAOIs) with 5-MeO-DMT increase brain exposure to 5-MeO-DMT by approximately 20-fold in animals. 5-MeO-DMT-d4 showed similar effects on locomotor activity in rodents as a combination of 5-MeO-DMT and a MAOI.
The chemical synthesis of 5-MeO-DMT-d4 has been described.
5-MeO-DMT-d4 was first described in the scientific literature by 1977. Subsequently, it was described in greater detail by Adam Halberstadt and David E. Nichols and colleagues in 2012. The study of 5-MeO-DMT-d4 was preceded by that of DMT-d4 which was described in the 1980s.