alpha-Methylserotonin
![]() α-Methyl-5-HT
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Routes of administration |
Oral |
ATC code | none |
Legal status | |
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Identifiers | |
Systematic (IUPAC) name: 3-(2-aminopropyl)-1H-indol-5-ol
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CAS Number | 304-52-9 ![]() |
PubChem (CID) | 2107 |
IUPHAR/BPS | 152 |
ChemSpider | 2023 ![]() |
ChEBI | CHEBI:48295 ![]() |
ChEMBL | CHEMBL275854 ![]() |
Chemical and physical data | |
Formula | C11H14N2O |
Molar mass | 190.242 g/mol |
3D model (Jmol) | Interactive image |
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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[edit]
United States[edit]
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[edit]
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[edit]
References[edit]
- ^ Ismaiel AM, Titeler M, Miller KJ, Smith TS, Glennon RA (February 1990). "5-HT1 and 5-HT2 binding profiles of the serotonergic agents alpha-methylserotonin and 2-methylserotonin". Journal of Medicinal Chemistry. 33 (2): 755–8. doi:10.1021/jm00164a046. PMID 2299641.
- ^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT".
- ^ Diksic M, Nagahiro S, Sourkes TL, Yamamoto YL (January 1990). "A new method to measure brain serotonin synthesis in vivo. I. Theory and basic data for a biological model". Journal of Cerebral Blood Flow and Metabolism. 10 (1): 1–12. doi:10.1038/jcbfm.1990.2. PMID 2298826.
- ^ a b Sourkes TL, Montine TJ, Missala K (1990). "Alpha-methylserotonin, a substitute transmitter for serotonergic neurons". Progress in Neuro-psychopharmacology & Biological Psychiatry. 14 (5): 829–32. doi:10.1016/0278-5846(90)90055-l. PMID 1705718.
- ^ a b Sourkes TL (1991). "Alpha-methyltryptophan as a therapeutic agent". Progress in Neuro-psychopharmacology & Biological Psychiatry. 15 (6): 935–8. doi:10.1016/0278-5846(91)90020-2. PMID 1763198.
- ^ "Erowid Online Books : "TIHKAL" - #5. a,O-DMS".
- ^ §1308.11 Schedule I.
- ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL