5-Methoxyharmalan

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5-Methoxyharmalan
File:5-Methoxyharmalan.svg
File:5-Methoxyharmalan 3D.png
Clinical data
Other names5-MeO-harmalan; 5-OMe-harmalan; 5-Methoxy-1-methyl-4,9-dihydro-3H-β-carboline
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 5-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
PubChem CID
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC13H14N2O
Molar mass214.268 g·mol−1
3D model (JSmol)
  • CC1=NCCC2=C1NC3=C2C(=CC=C3)OC
  • InChI=1S/C13H14N2O/c1-8-13-9(6-7-14-8)12-10(15-13)4-3-5-11(12)16-2/h3-5,15H,6-7H2,1-2H3
  • Key:RFGOJFHLZUEUIV-UHFFFAOYSA-N

5-Methoxyharmalan, also known as 5-methoxy-1-methyl-4,9-dihydro-3H-β-carboline, is a serotonin receptor modulator of the β-carboline family.[1][2][3] It is a cyclized tryptamine analogue of 4-MeO-DMT and a positional isomer of 6-methoxyharmalan and harmaline (7-methoxyharmalan).[2][3]

Pharmacology

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The drug shows high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 86–137 nM and 69 nM, respectively).[2][3] It had higher affinity for these receptors than any other assessed β-carboline, with 1.7–4.6-fold, 57–58-fold, and >73–116-fold the affinity of harmine, harmaline, and tetrahydroharmine for the serotonin 5-HT2A receptor, respectively.[2][3] However, like harmaline and 6-methoxyharmalan, 5-methoxyharmalan showed no agonist or antagonist activity at the serotonin 5-HT2A receptor in terms of phosphatidylinositol (PI) hydrolysis in vitro at concentrations of up to 10,000 nM (and harmaline further showed no agonist activity in this assay at up to 20,000 nM).[2] It is unclear whether the serotonin 5-HT2A receptor is involved in the hallucinogenic or other psychoactive effects of β-carbolines.[2][3]

5-Methoxyharmalan showed no affinity for the melatonin receptors.[4] The 1-demethyl analogue of 5-methoxyharmalan shows high affinity for the imidazoline I2 receptor and the α2 receptor, whereas 5-methoxyharmalan itself was not assessed.[5]

History

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5-Methoxyharmalan was first described in the scientific literature by 1993.[4]

See also

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References

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