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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
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)
  • 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,4,12H2,1H3 checkY
  • Key:LYPCGXKCQDYTFV-UHFFFAOYSA-N checkY
  (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]

Pharmacology

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αMS is a non-selective and near-full agonist of the serotonin 5-HT2 receptors.[2] It has similar affinity for the 5-HT2A, 5-HT2B, and 5-HT2C receptors.[2] The drug is also a ligand of the serotonin 5-HT1 receptors with high affinity, including of the serotonin 5-HT1A, 5-HT1B, and 5-HT1D receptors (Ki = 40–150 nM), but not of the serotonin 5-HT1E receptor (Ki > 10,000 nM).[1] In addition to its actions at the serotonin receptors, αMS has been found to act as a norepinephrine releasing agent similarly to α-methylphenylalanine and to other α-alkylated tryptamines.[3][4][5]

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.[6][7] 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.[6]

Chemistry

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αMS, also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT), is a substituted tryptamine derivative and the α-methylated analogue of serotonin (5-hydroxytryptamine or 5-HT).

The predicted log P (XLogP3) of αMS is 0.6.[8]

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United States

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αMS is not scheduled at the federal level in the United States,[9] but it could be considered an analogue of α-methyltryptamine (AMT), in which case, purchase, sales, or possession could be prosecuted under the Federal Analog Act.

Florida

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αMS is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[10]

Other drugs

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α-Methyltryptophan (αMTP) and α-methyl-5-hydroxytryptophan (α-Me-5-HTP) are prodrugs of αMS which cross the blood–brain barrier and thus efficiently deliver αMS into the central nervous system.[11][12] As a result, these compounds act as orally bioavailable false or substitute neurotransmitters for serotonin, and have been suggested as possible therapeutic agents in the treatment of disorders where serotonin is deficient.[11][12] The O-methylated analogue of αMS, 5-MeO-αMT, also readily enters the brain, and could be used for such purposes as well.[6][13]

See also

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References

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  1. ^ a b 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 Maroteaux L, Ayme-Dietrich E, Aubertin-Kirch G, Banas S, Quentin E, Lawson R, Monassier L (February 2017). "New therapeutic opportunities for 5-HT2 receptor ligands". Pharmacol Ther. 170: 14–36. doi:10.1016/j.pharmthera.2016.10.008. PMID 27771435. alpha-methyl-5-HT is a non-selective nearly full agonist at 5-HT2 receptors with similar affinity to 5-HT2A 5-HT2B and 5-HT2C receptors (Jerman, et al., 2001; Knight, et al., 2004; Porter, et al., 1999).
  3. ^ Lahti RA, Platz PA, Heinzelman RV (July 1969). "Effects of alpha-methyl-5-hydroxytryptophan and alpha-methyl-5-hydroxytryptamine on norepinephrine in mouse myocardium". Biochem Pharmacol. 18 (7): 1601–1608. doi:10.1016/0006-2952(69)90147-6. PMID 5306701.
  4. ^ Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC 4194234. PMID 24800892.
  5. ^ Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
  6. ^ a b c "Erowid Online Books : "TIHKAL" - #48 a-MT".
  7. ^ 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.
  8. ^ "3-(2-aminopropyl)-1H-indol-5-ol". PubChem. Retrieved 7 October 2024.
  9. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  10. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
  11. ^ 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. S2CID 25604266.
  12. ^ 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. S2CID 31504647.
  13. ^ "Erowid Online Books : "TIHKAL" - #5. a,O-DMS".
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