Alpha-Methylserotonin
From Wikipedia, the free encyclopedia
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|---|---|
| Systematic (IUPAC) name | |
| 3-(2-aminopropyl)-1H-indol-5-ol | |
| Clinical data | |
| Legal status | Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries) |
| Routes | Oral |
| Identifiers | |
| CAS number | 304-52-9  |
| ATC code | None |
| PubChem | CID 2107 |
| IUPHAR ligand | 152 |
| ChemSpider | 2023 |
| ChEBI | CHEBI:48295 |
| ChEMBL | CHEMBL275854 |
| Chemical data | |
| Formula | C11H14N2O |
| Mol. mass | 190.242 g/mol |
| SMILES
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| (what is this?) (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, and 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 mental effects.[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 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 may be used for this purpose as well.[2][6]
See also
- 2-Methyl-5-hydroxytryptamine
- 5-Carboxamidotryptamine
- 5-Methoxytryptamine
- α-Methyldopamine
References
- ↑ 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.
- ↑ 2.0 2.1 2.2 "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.
- ↑ 4.0 4.1 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. PMID 1705718.
- ↑ 5.0 5.1 Sourkes TL (1991). "Alpha-methyltryptophan as a therapeutic agent". Progress in Neuro-psychopharmacology & Biological Psychiatry 15 (6): 935–8. PMID 1763198.
- ↑ "Erowid Online Books : "TIHKAL" - #5. a,O-DMS".
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