N-Methylmescaline


N-Methylmescaline, also known as methylmescaline, is an alkaloid and serotonin receptor modulator of the phenethylamine family related to mescaline that occurs naturally in cacti including Lophophora williamsii, Pelecyphora aselliformis, and Pachycereus pringlei, among others.

Use and effects

According to Alexander Shulgin, N-methylmescaline shows no central or peripheral effects at doses of up to 24 or 25mg, which is many times the minor or trace amounts present in peyote. Nonetheless, according to Shulgin, N-methylmescaline, in combination with potent isoquinoline monoamine oxidase inhibitors that are also present in the cactus, might be the active psychedelic constituent of Pachycereus pringlei, which notably does not contain mescaline.

Pharmacology

Pharmacodynamics

N-Methylmescaline shows weak affinity for serotonin receptors similarly to mescaline. It was found to have about half the serotonin receptor affinity as mescaline.
N-Methylmescaline failed to significantly substitute for mescaline in rodent drug discrimination tests either with intraperitoneal or intracerebroventricular injection. In contrast to N-methylmescaline however, trichocereine produced similar effects to mescaline at a dose of 50mg/kg intraperitoneally, whereas it only transiently substituted for mescaline when given intracerebroventricularly. Trichocereine has also been reported to be psychedelic in humans, although findings in this area are controversial and conflicting. It has been noted that N-methylation of psychedelic phenethylamines, for instance Beatrice, has invariably eliminated their hallucinogenic activity.
N-Methylmescaline is less toxic than mescaline in terms of lethal doses in animals.

Chemistry

N-Methylmescaline, also known as N-methyl-3,4,5-trimethoxyphenethylamine, is a substituted phenethylamine and scaline. It is specifically the N-methyl analogue of mescaline.

Synthesis

The chemical synthesis of N-methylmescaline has been described.

Analogues

Notable analogues of N-methylmescaline, besides mescaline, include trichocereine and N-acetylmescaline. Other psychedelic-related N-methylphenethylamines include methyl-TMA, Beatrice, N-methyl-DOET, N-methyl-DOB, N-methyl-2C-I, N-methyl-DMA, N-methyl-MMDA-2, and MDMA.

History

N-Methylmescaline was first described in the scientific literature by Ernst Späth and Johann Bruck in 1937. It was isolated from Lophophora williamsii by the researchers and was also synthesized.

Society and culture

Legal status

Canada

N-Methylmescaline is not a controlled substance in Canada as of 2025.

United States

N-Methylmescaline is not an explicitly controlled substance in the United States. However, it may be considered controlled in this country as it is a positional isomer of 3,4,5-trimethoxyamphetamine, which is a specifically regulated substance.