''N''-Methylserotonin is a

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

alkaloid. Chemically, it is a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

of serotonin in which a

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ma ...

resides at its alkyl amine. It is also called ''N''_ω-methylserotonin (''N''_ω-methyl-5-hydroxytryptamine) to distinguish it from tryptamine-derived compounds in which a methyl group is bonded to the nitrogen atom of the

indole Indole is an aromatic heterocyclic organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other c ...

group. ''N''-Methylserotonin is found in plants, animals, and fungi. These include the plants, '' Actaea racemosa'' (black cohosh) and ''

Zanthoxylum piperitum ''Zanthoxylum piperitum'', also known as Japanese pepper or Japanese prickly-ash is a deciduous aromatic spiny shrub or small tree of the citrus and rue family Rutaceae, native to Japan and Korea. It is called sanshō () in Japan and chopi () ...

'', the Green and Golden Bell Frog, ''

Litoria aurea The green and golden bell frog (''Ranoidea aurea''), also named the green bell frog, green and golden swamp frog and green frog, is a species of ground-dwelling tree frog native to eastern Australia. Despite its classification and climbing abi ...

'', and ''

Amanita The genus ''Amanita'' contains about 600 species of agarics, including some of the most toxic known mushrooms found worldwide, as well as some well-regarded edible species. This genus is responsible for approximately 95% of the fatalities resul ...

'' mushrooms. The compound binds to several

serotonin receptors 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory neur ...

, including the 5-HT₇ and 5-HT_1A receptors, with high affinity ( IC₅₀ ≤ 2 nM) and selectivity, and displays agonist activity; besides its direct interaction with the

, ''N''-methylserotonin also acts as a

selective serotonin reuptake inhibitor Selective serotonin reuptake inhibitors (SSRIs) are a class of drugs that are typically used as antidepressants in the treatment of major depressive disorder, anxiety disorders, and other psychological conditions. SSRIs increase the extracellul ...

Legal Status

United States

''N''-Methylserotonin is not scheduled at the federal level in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

,§1308.11 Schedule I.
/ref> but could be considered an analog (of

bufotenin Bufotenin (5-HO-DMT, bufotenine) is a tryptamine derivative - more specifically, a DMT derivative - related to the neurotransmitter serotonin. It is an alkaloid found in some species of toads (especially the skin), mushrooms and plants. ...

), in which case, sales or possession intended for human consumption could be prosecuted under the

Federal Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

Florida

''N''-Methylserotonin is a Schedule I

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Single ...

in the state of

Florida Florida is a state located in the Southeastern region of the United States. Florida is bordered to the west by the Gulf of Mexico, to the northwest by Alabama, to the north by Georgia, to the east by the Bahamas and Atlantic Ocean, and to ...

making it illegal to buy, sell, or possess in Florida.Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
/ref>

References

{{DEFAULTSORT:Methylserotonin, N- 5-HT1A agonists 5-HT7 agonists Serotonin receptor agonists Tryptamines