Chemistry:Mebfap

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Mebfap, also known as 1-(5-methoxybenzofuran-3-yl)-2-aminopropane or 5-methoxy-3-(2-aminopropyl)benzofuran (5-MeO-3-APB) as well as 1-oxa-5-MeO-AMT, is a serotonin receptor modulator of the benzofuran family related to the psychedelic tryptamine 5-MeO-AMT.[1][2][3] It is the analogue and bioisostere of 5-MeO-AMT in which the nitrogen atom of the indole ring has been replaced with an oxygen atom, resulting in the drug being a benzofuran rather than tryptamine derivative.[1][2][3] Mebfap is a ligand of serotonin receptors similarly to 5-MeO-AMT, but shows about 6-fold lower affinity than 5-MeO-AMT.[1][2][3] It was first described in the scientific literature by David E. Nichols and colleagues by 1992.[3]

See also

References

  1. ↑ 1.0 1.1 1.2 Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. "Replacing the indole nitrogen of the tryptamines with an oxygen atom affords a benzo[b]furan, another potential bioisostere of tryptamines. Compounds 13 and 14 both had about one-sixth the affinity of their indole congeners, using displacement of [125I]DOI from rat frontal cortical homogenate (Tomaszewski et al. 1992). McKenna et al. (1990) reported a similar finding, assessing ability of N-methyl-N-isopropyltryptamine to displace [125I]-R-DOI from rat cortical homogenate, compared with its benzo[b]furan isostere. The tryptamine IC50 of 38 nM was about 13-fold lower than the benzofuran, which had an IC50 of 500 nM." 
  2. ↑ 2.0 2.1 2.2 "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. 2012. doi:10.1002/wmts.42. ISSN 2190-460X. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=e28e0e22c3145af5a787c34fbedbaa8f81e1ed6b. Retrieved 7 February 2025. "Other potential bioisosteres of tryptamines would include replacing the indole N with an oxygen atom to give benzo[b]furans (Figure 7). The dimethylamino compound 10 and the racemic α-methyl congener 11 both had about one-sixth the affinity of their indole congeners, measured using displacement of [125I]DOI from rat frontal cortical homogenate.10 This result parallels the findingsby McKenna et al.,4 who compared N-methyl-Nisopropyltryptamine with its benzofuran isostere in its ability to displace [125I]-R-DOI from rat cortical homogenate. In that report, the tryptamine had an IC50 of 38 nM whereas the benzofuran IC50 was 500 nM, 13-fold lower affinity. [...] FIGURE 7 | Benzofuran bioisosteres of tryptamines.". 
  3. ↑ 3.0 3.1 3.2 3.3 "Benzofuran bioisosteres of hallucinogenic tryptamines". Journal of Medicinal Chemistry 35 (11): 2061–2064. May 1992. doi:10.1021/jm00089a017. PMID 1534585. 



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