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Mebfap

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Pharmaceutical compound
Mebfap
Clinical data
Other namesMEBFAP; 1-(5-Methoxybenzofuran-3-yl)-2-aminopropane; 5-Methoxy-3-(2-aminopropyl)benzofuran; 5-MeO-3-APB; 3-(2-Aminopropyl)-5-methoxybenzofuran
Drug classSerotonin receptormodulator
Identifiers
  • 1-(5-methoxy-1-benzofuran-3-yl)propan-2-amine
CAS Number
PubChemCID
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 as1-(5-methoxybenzofuran-3-yl)-2-aminopropane, is aserotonin receptormodulator of thebenzofuran family.[1][2][3] It is ananalogue of5-MeO-AMT in which theindolering has been replaced with abenzofuran ring.[1][2][3] Put another way, it is the analogue of 5-MeO-AMT in which thenitrogenatom in its indole ring has been replaced with acarbon atom to make a benzofuran ring.[1][2][3] The drug is aligand of serotonin receptors similarly to 5-MeO-AMT, but shows about one-sixth theaffinity of 5-MeO-AMT.[1][2][3] Mebfap was first described in thescientific literature by 1992.[3]

See also

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References

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  1. ^abcdNichols 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. ^abcdNichols 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. Retrieved7 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. ^abcdeTomaszewski 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.

External links

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