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α-Methylserotonin

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α-Methylserotonin
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-(2-aminopropyl)-1H-indol-5-ol
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246g·mol−1
3D model (JSmol)
  • c2cc(O)cc1c2[nH]cc1CC(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,4,12H2,1H3checkY
  • Key:LYPCGXKCQDYTFV-UHFFFAOYSA-NcheckY
(verify)

α-Methylserotonin(αMS), also known asα-methyl-5-hydroxytryptamine(α-methyl-5-HT) or5-hydroxy-α-methyltryptamine(5-HO-αMT), is atryptaminederivativeclosely related to theneurotransmitterserotonin(5-HT). It acts as a non-selectiveserotonin receptor agonistand has been used extensively inscientific researchto study the function of the serotonin system.[1]

Unlike serotonin, αMS is notmetabolizedbymonoamine oxidaseon account of the α-methylsubstituentblocking theenzyme'saccess to theamine.As a result, it has a much longerhalf-lifein comparison.[2][3]Similarly to serotonin however, αMS poorly crosses theblood-brain-barrierdue to its freehydroxylgroup,and thus has only weak or nocentraleffects when administeredperipherally.[2]

α-Methyltryptophan(αMTP) is aprodrugto 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 anorallybioavailablefalseorsubstitute neurotransmitterfor serotonin, and has been suggested as a possible therapeutic agent in the treatment of disorders where serotonin is deficient.[4][5]TheO-methylatedanalogueof αMS,5-MeO-αMT,also readily enters the brain and could be used for this purpose as well.[2][6]

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United States

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5-Hydroxy-alpha-methyltryptamine is not scheduled at the federal level in theUnited States,[7]but it could be considered an analog ofalpha-methyltryptamine(AMT), in which case, purchase, sales, or possession could be prosecuted under theFederal Analog Act.

Florida

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5-Hydroxy-alpha-methyltryptamine is a Schedule Icontrolled substancein the state ofFloridamaking it illegal to buy, sell, or possess in Florida.[8]

See also

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References

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  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.PMID2299641.
  2. ^abc"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.PMID2298826.
  4. ^abSourkes 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.PMID1705718.S2CID25604266.
  5. ^abSourkes 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.PMID1763198.S2CID31504647.
  6. ^"Erowid Online Books:" TIHKAL "- #5. a,O-DMS".
  7. ^"§1308.11 Schedule I."Archived fromthe originalon 2009-08-27.Retrieved2014-12-17.
  8. ^Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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