Jump to content

5-Methoxyharmalan

Add links
From Wikipedia, the free encyclopedia
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
PubChem CID
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 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]

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]

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

See also

[edit]

References

[edit]
  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. ^ a b c d e f Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, Smith C, Egan C, Davis K, Mattson MV (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 Alcohol Depend. 60 (2): 121–132. doi:10.1016/s0376-8716(99)00148-9. hdl:11380/17721. PMID 10940539.
  3. ^ a b c d e Grella B, Dukat M, Young R, Teitler M, Herrick-Davis K, Gauthier CB, Glennon RA (April 1998). "Investigation of hallucinogenic and related beta-carbolines". Drug Alcohol Depend. 50 (2): 99–107. doi:10.1016/s0376-8716(97)00163-4. PMID 9649961.
  4. ^ a b Song Y, Poon AM, Lee PP, Pang SF (October 1993). "Putative melatonin receptors in the male guinea pig kidney". J Pineal Res. 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". Bioorg Med Chem Lett. 14 (4): 999–1002. doi:10.1016/j.bmcl.2003.11.078. PMID 15013009.
[edit]



Stub icon

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=5-Methoxyharmalan&oldid=1296209304"