Chemistry:5-Methoxyharmalan

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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

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

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

See also

References

  1. ↑ "Resource distribution, pharmacological activity, toxicology and clinical drugs of β-Carboline alkaloids: An updated and systematic review". Fitoterapia 180. January 2025. doi:10.1016/j.fitote.2024.106326. PMID 39645053. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence 60 (2): 121–132. August 2000. doi:10.1016/s0376-8716(99)00148-9. PMID 10940539. https://psilosybiini.info/paperit/Binding%20of%20%DF-carbolines%20and%20related%20agents%20at%20serotonin%20(5-HT2%20and%205-HT1A),%20dopamine%20(D2)%20and%20benzodiazepine%20receptors%20(Glennon%20et%20al.,%202000).pdf. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "Investigation of hallucinogenic and related beta-carbolines". Drug and Alcohol Dependence 50 (2): 99–107. April 1998. doi:10.1016/s0376-8716(97)00163-4. PMID 9649961. 
  4. ↑ 4.0 4.1 "Putative melatonin receptors in the male guinea pig kidney". Journal of Pineal Research 15 (3): 153–160. October 1993. doi:10.1111/j.1600-079x.1993.tb00523.x. PMID 8106962. 
  5. ↑ "Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation". Bioorganic & Medicinal Chemistry Letters 14 (4): 999–1002. February 2004. doi:10.1016/j.bmcl.2003.11.078. PMID 15013009. 




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