5-Methoxytryptamine

5-Methoxytryptamine
Clinical data
Other names5-MeO-T; 5-OMe-T; 5-MeOT; 5-MeO-TPA; 5-MT; MT; 5-Hydroxytryptamine methyl ether; Serotonin methyl ether; O-Methylserotonin; O-Methyl-5-HT; Mexamine; Meksamin; Mekasamin; PAL-234
Routes of
administration		Orally inactive[1][2]
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Pharmacokinetic data
MetabolismMAO-ATooltip Monoamine oxidase A
Identifiers
IUPAC name
  • 2-(5-Methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.231
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
SMILES
  • O(c1cc2c(cc1)[nH]cc2CCN)C
InChI
  • InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3 Y
  • Key:JTEJPPKMYBDEMY-UHFFFAOYSA-N Y
  (verify)

5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or O-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin.[3] It has been shown to occur naturally in the body in low levels, especially in the pineal gland.[3][4] It is formed via O-methylation of serotonin or N-deacetylation of melatonin.[3][5][4]

5-MT is a highly potent and non-selective serotonin receptor agonist[6][7][8][9] and shows serotonergic psychedelic-like effects in animals.[10] However, it is inactive in humans, at least orally, likely due to rapid metabolism by monoamine oxidase (MAO).[1][2] The levels and effects of 5-MT are dramatically potentiated by monoamine oxidase inhibitors (MAOIs) in animals.[11][12][13][14][15][16]

  1. ^ a b Cite error: The named reference Nichols2012 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference Nichols2018 was invoked but never defined (see the help page).
  3. ^ a b c Pévet P (1983). "Is 5-methoxytryptamine a pineal hormone?". Psychoneuroendocrinology. 8 (1): 61–73. doi:10.1016/0306-4530(83)90041-0. PMID 6136058.
  4. ^ a b Galzin AM, Eon MT, Esnaud H, Lee CR, Pévet P, Langer SZ (1988). "Day-night rhythm of 5-methoxytryptamine biosynthesis in the pineal gland of the golden hamster (Mesocricetus auratus)". J. Endocrinol. 118 (3): 389–397. doi:10.1677/joe.0.1180389. PMID 2460575.
  5. ^ Cite error: The named reference TanHardelandBack2016 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference PDSPKiDatabase was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference BindingDB was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference BloughLandavazoPartilla2014 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference BloughLandavazoDecker2014 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference PrzegalińskiZebrowska-LupinaWójcik1977 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference GreenHughesTordoff1975 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference ProzialekVogel1978 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference ProzialeckVogel1979 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference RaynaudPévet1991 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference VetulaniByrskaReichenberg1979 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference KolasaKleinrokRajtar1984 was invoked but never defined (see the help page).
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