Edge Rewrite
restyle Source code View original
// HTMLRewriter · presentation

This page was redesigned at the edge.

Cloudflare fetched the original article and streamed it through HTMLRewriter to apply an entirely new visual system without rebuilding the source page.

Jump to content

Mebfap

Add links
From Wikipedia, the free encyclopedia

Mebfap
Clinical data
Other namesMEBFAP; 1-(5-Methoxybenzofuran-3-yl)-2-aminopropane; 5-Methoxy-3-(2-aminopropyl)benzofuran; 3-(2-Aminopropyl)-5-methoxybenzofuran; 5-MeO-3-APB
Drug classSerotonin receptor modulator
Identifiers
  • 1-(5-methoxy-1-benzofuran-3-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC12H15NO2
Molar mass205.257 g·mol−1
3D model (JSmol)
  • CC(CC1=COC2=C1C=C(C=C2)OC)N
  • InChI=1S/C12H15NO2/c1-8(13)5-9-7-15-12-4-3-10(14-2)6-11(9)12/h3-4,6-8H,5,13H2,1-2H3
  • Key:PMAFEFSQHHKAKM-UHFFFAOYSA-N

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

[edit]

References

[edit]
  1. 1 2 3 Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. 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. 1 2 3 Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A 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. 1 2 3 4 Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 35 (11): 2061–2064. doi:10.1021/jm00089a017. PMID 1534585.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=Mebfap&oldid=1332267773"