Mebfap, also known as 1-(5-methoxybenzofuran-3-yl)-2-aminopropane, is a serotonin receptor modulator of the benzofuran family.[1][2][3] It is an analogue of 5-MeO-AMT in which the indole ring has been replaced with a benzofuran ring.[1][2][3] Put another way, it is the analogue of 5-MeO-AMT in which the nitrogen atom in its indole ring has been replaced with a carbon atom to make a benzofuran ring.[1][2][3] The drug is a ligand of serotonin receptors similarly to 5-MeO-AMT, but shows about one-sixth the affinity of 5-MeO-AMT.[1][2][3] Mebfap was first described in the scientific literature by 1992.[3]

See also

References

  1. ^ a b c d Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Curr Top Behav Neurosci. 36: 1–43. doi:10.1007/7854_2017_475. PMID 28401524. 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. ^ a b c d Nichols, David E. (2012). "Structure–activity relationships of serotonin 5‐HT 2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. 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. ^ a b c d e Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines". J Med Chem. 35 (11): 2061–2064. doi:10.1021/jm00089a017. PMID 1534585.


Allikas: https://en.wikipedia.org/wiki/Mebfap
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