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5-Methoxyharmalan

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Pharmaceutical compound
5-Methoxyharmalan
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
PubChemCID
ChemSpider
ChEMBL
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 as5-methoxy-1-methyl-4,9-dihydro-3H-β-carboline, is aserotonin receptor modulator of theβ-carboline family.[1][2][3] It is acyclized tryptamineanalogue of4-MeO-DMT and apositional isomer of6-methoxyharmalan andharmaline (7-methoxyharmalan).[2][3]

Pharmacology

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The drug shows highaffinity for theserotonin5-HT2A and5-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 ofharmine, harmaline, andtetrahydroharmine for the serotonin 5-HT2A receptor, respectively.[2][3] However, like harmaline and 6-methoxyharmalan, 5-methoxyharmalan showed noagonist orantagonist activity at the serotonin 5-HT2A receptor in terms ofphosphatidylinositol (PI)hydrolysisin 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 thehallucinogenic or otherpsychoactive effects of β-carbolines.[2][3]

5-Methoxyharmalan showed no affinity for themelatonin receptors.[4] The 1-demethyl analogue of 5-methoxyharmalan shows high affinity for theimidazolineI2 receptor and theα2 receptor, whereas 5-methoxyharmalan itself was not assessed.[5]

History

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

See also

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References

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  1. ^Yu L, Shen N, Ren J, Xin H, Cui Y (January 2025). "Resource distribution, pharmacological activity, toxicology and clinical drugs of β-Carboline alkaloids: An updated and systematic review".Fitoterapia.180 106326.doi:10.1016/j.fitote.2024.106326.PMID 39645053.
  2. ^abcdefGlennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000)."Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors"(PDF).Drug and Alcohol Dependence.60 (2):121–132.doi:10.1016/s0376-8716(99)00148-9.hdl:11380/17721.PMID 10940539.
  3. ^abcdeGrella B, Dukat M, Young R, Teitler M, Herrick-Davis K, Gauthier CB, et al. (April 1998). "Investigation of hallucinogenic and related beta-carbolines".Drug and Alcohol Dependence.50 (2):99–107.doi:10.1016/s0376-8716(97)00163-4.PMID 9649961.
  4. ^abSong Y, Poon AM, Lee PP, Pang SF (October 1993). "Putative melatonin receptors in the male guinea pig kidney".Journal of Pineal Research.15 (3):153–160.doi:10.1111/j.1600-079x.1993.tb00523.x.PMID 8106962.
  5. ^Glennon RA, Grella B, Tyacke RJ, Lau A, Westaway J, Hudson AL (February 2004). "Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation".Bioorganic & Medicinal Chemistry Letters.14 (4):999–1002.doi:10.1016/j.bmcl.2003.11.078.PMID 15013009.

External links

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5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
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