alpha-Methylserotonin

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α-Methylserotonin
5-HO-AMT structure.png
α-Methyl-5-HT
Systematic (IUPAC) name
3-(2-aminopropyl)-1H-indol-5-ol
Clinical data
Legal status
Routes of
administration
Oral
Identifiers
CAS Number 304-52-9 YesY
ATC code none
PubChem CID: 2107
IUPHAR/BPS 152
ChemSpider 2023 YesY
ChEBI CHEBI:48295 YesY
ChEMBL CHEMBL275854 YesY
Chemical data
Formula C11H14N2O
Molecular mass 190.242 g/mol
  • c2cc(O)cc1c2ncc1CC(N)C
  • InChI=1S/C11H14N2O/c1-7(12)4-8-6-13-11-3-2-9(14)5-10(8)11/h2-3,5-7,13-14H,4,12H2,1H3 YesY
  • Key:LYPCGXKCQDYTFV-UHFFFAOYSA-N YesY
  (verify)

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 serotonin (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.[1]

Unlike serotonin, αMS is not metabolized by monoamine oxidase on account of the α-methyl substituent blocking the enzyme access to the amine. As a result, it has a much longer half-life in comparison.[2][3] 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 effects when administered peripherally.[2]

α-Methyltryptophan (αMTP) is a prodrug to αMS which does cross the blood-brain-barrier and thus efficiently delivers αMS into the central nervous system.[4][5] 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.[4][5] The O-methylated analogue of αMS, 5-MeO-αMT, also readily enters the brain and could be used for this purpose as well.[2][6]

Legal status

United States

5-Hydroxy-alpha-methyltryptamine is not scheduled at the federal level in the United States,[7] 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.[8]

See also

References

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  7. §1308.11 Schedule I.
  8. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL