alpha-Methylserotonin

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α-Methylserotonin
5-HO-AMT structure.png
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 YesY
ATC code None
PubChem CID 2107
IUPHAR ligand 152
ChemSpider 2023 YesY
ChEBI CHEBI:48295 YesY
ChEMBL CHEMBL275854 YesY
Chemical data
Formula C11H14N2O 
Mol. mass 190.242 g/mol
 YesY (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[edit]

References[edit]

  1. ^ 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. ^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT". 
  3. ^ 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. ^ 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. 
  5. ^ 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. 
  6. ^ "Erowid Online Books : "TIHKAL" - #5. a,O-DMS".