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α-Methylmelatonin

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α-Methylmelatonin
Clinical data
Other namesα-Methyl-5-methoxy-N-acetyltryptamine; α-Methyl-N-acetyl-5-methoxytryptamine
Chemical and physical data
FormulaC14H18N2O2
Molar mass246.310 g·mol−1
3D model (JSmol)
  • O(C)C1C=CC2=C(C=1)C(=CN2[H])CC(C)N([H])C(C)=O
  • InChI=1S/C14H18N2O2/c1-9(16-10(2)17)6-11-8-15-14-5-4-12(18-3)7-13(11)14/h4-5,7-9,15H,6H2,1-3H3,(H,16,17)
  • Key:KEFHUIZLNNJKEM-UHFFFAOYSA-N

α-Methylmelatonin, also known as α-methyl-5-methoxy-N-acetyltryptamine, is a synthetic tryptamine derivative and analogue of the monoamine neurotransmitter melatonin.[1] It is a metabolite of α-methyltryptophan, α-methyl-5-hydroxytryptophan, and α-methylserotonin that can be formed in small amounts via aralkylamine N-acetyltransferase (AANAT).[1] α-Methyltryptophan and α-methyl-5-hydroxytryptophan are prodrugs of α-methylserotonin that have serotonergic actions and have been suggested for potential therapeutic use.[2][3][4][5] However, while formation of α-methylmelatonin can occur from these compounds, α-alkylated tryptamines show 95% reduced suitability as substrates for AANAT compared to non-α-alkylated tryptamines in vitro and no α-methylmelatonin could be detected with administration of α-methyltryptophan in vivo in animals.[1] α-Methyl-N-acetylserotonin is an intermediate is the formation of α-methylmelatonin from α-methylserotonin.[1][6]

References

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  1. ^ a b c d Montine TJ, Missala K, Sourkes TL (January 1992). "Alpha-methyltryptophan metabolism in rat pineal gland and brain". J Pineal Res. 12 (1): 43–48. doi:10.1111/j.1600-079x.1992.tb00024.x. PMID 1564632.
  2. ^ Sourkes TL (1991). "Alpha-methyltryptophan as a therapeutic agent". Prog Neuropsychopharmacol Biol Psychiatry. 15 (6): 935–938. doi:10.1016/0278-5846(91)90020-2. PMID 1763198.
  3. ^ Diksic M, Young SN (September 2001). "Study of the brain serotonergic system with labeled alpha-methyl-L-tryptophan". J Neurochem. 78 (6): 1185–1200. doi:10.1046/j.1471-4159.2001.00536.x. PMID 11579128.
  4. ^ Sourkes TL (1993). "Conversion of alpha-methyltryptophan to alpha-methylserotonin in vivo. New techniques for imaging serotonin". Adv Neurol. 60: 515–518. PMID 8420181.
  5. ^ Diksic M, Grdisa M (November 1995). "Alpha-methyl-L-tryptophan as a tracer to study brain serotonergic system". Neurochem Res. 20 (11): 1353–1360. doi:10.1007/BF00992511. PMID 8786822.
  6. ^ "CID 54262547". PubChem. Retrieved 8 October 2024.
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