alpha-Methylserotonin

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]

α-Methylserotonin
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Identifiers
IUPAC name
  • 3-(2-aminopropyl)-1H-indol-5-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
SMILES
  • c2cc(O)cc1c2[nH]cc1CC(N)C
InChI
  • 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 Y
  • Key:LYPCGXKCQDYTFV-UHFFFAOYSA-N Y
  (verify)

Unlike serotonin, αMS is not metabolized by monoamine oxidase on account of the α-methyl substituent blocking the enzyme's 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]

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
  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. "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. 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. S2CID 25604266.
  5. 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. S2CID 31504647.
  6. "Erowid Online Books : "TIHKAL" - #5. a,O-DMS".
  7. §1308.11 Schedule I.
  8. Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
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