α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a
tryptamine derivative closely related to the
neurotransmitter
A neurotransmitter is a signaling molecule secreted by a neuron to affect another cell across a synapse. The cell receiving the signal, any main body part or target cell, may be another neuron, but could also be a gland or muscle cell.
Neuro ...
serotonin
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...
(5-HT). It acts as a non-
selective serotonin receptor agonist and has been used extensively in
scientific research to study the function of the serotonin system.
Unlike serotonin, αMS is not
metabolized
Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
by
monoamine oxidase
Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The first ...
on account of the α-
methyl
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 many ...
substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side ...
blocking the
enzyme's access to the
amine. As a result, it has a much longer
half-life in comparison.
Similarly to serotonin however, αMS poorly crosses the
blood-brain-barrier due to its free
hydroxyl group, and thus has only weak or no
central
Central is an adjective usually referring to being in the center of some place or (mathematical) object.
Central may also refer to:
Directions and generalised locations
* Central Africa, a region in the centre of Africa continent, also known as ...
effects when administered
peripheral
A peripheral or peripheral device is an auxiliary device used to put information into and get information out of a computer. The term ''peripheral device'' refers to all hardware components that are attached to a computer and are controlled by the ...
ly.
(αMTP) is a
prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
to αMS which does cross the blood-brain-barrier and thus efficiently delivers αMS into the central nervous system.
As a result, αMTP acts as an
orally
bioavailable false or
substitute neurotransmitter for serotonin, and has been suggested as a possible therapeutic agent in the treatment of disorders where serotonin is deficient.
The ''O''-
methyl
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 many ...
ated
analogue of αMS,
5-MeO-αMT, also readily enters the brain and could be used for this purpose as well.
Legal status
United States
5-Hydroxy-alpha-methyltryptamine is not scheduled at the federal level in the
United States,
[§1308.11 Schedule I.](_blank)
/ref> but it could be considered an analog of alpha-methyltryptamine (AMT), in which case, purchase, sales, or possession could be prosecuted under the Federal Analog Act.
Florida
5-Hydroxy-alpha-methyltryptamine is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL](_blank)
/ref>
See also
* 2-Methyl-5-hydroxytryptamine
2-Methyl-5-hydroxytryptamine (2-Methylserotonin, 2-Methyl-5-HT) is a tryptamine derivative closely related to the neurotransmitter serotonin which acts as a moderately selective full agonist at the 5-HT3 receptor.
See also
* 5-Carboxamidotry ...
* 5-Carboxamidotryptamine
5-Carboxamidotryptamine (5-CT) is a tryptamine derivative closely related to the neurotransmitter serotonin.
5-CT acts as a non-selective, high-affinity full agonist at the 5-HT1A, 5-HT1B, 5-HT1D, 5-HT5A, and 5-HT7 receptors, as well as ...
* 5-Methoxytryptamine
5-Methoxytryptamine (5-MT), also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels. It is biosynthesized via the deacet ...
* α-Methyldopamine
* Serotonin
Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...
References
{{DEFAULTSORT:Methylserotonin, alpha-
5-HT2B agonists
Psychedelic tryptamines
Serotonin receptor agonists
Tryptamines
Phenols
Peripherally selective drugs