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MiPBF

MiPBF
Clinical data
Other namesMethylisopropylbenzofuran; MIPBF; N-Methyl-N-isopropyl-3-(2-aminoethyl)benzofuran; 1-Oxa-N-methyl-N-isopropyltryptamine; 1-Oxa-MiPT
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • N-[2-(1-benzofuran-3-yl)ethyl]-N-methylpropan-2-amine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC14H19NO
Molar mass217.312 g·mol−1
3D model (JSmol)
  • CC(C)N(C)CCC1=COC2=CC=CC=C21
  • InChI=1S/C14H19NO/c1-11(2)15(3)9-8-12-10-16-14-7-5-4-6-13(12)14/h4-7,10-11H,8-9H2,1-3H3
  • Key:HNYJKEQVSSYBRE-UHFFFAOYSA-N

MiPBF, also known as N-methyl-N-isopropyl-3-(2-aminoethyl)benzofuran or as 1-oxa-N-methyl-N-isopropyltryptamine (1-oxa-MiPT), is a serotonin receptor modulator of the benzofuran family related to the psychedelic tryptamine methylisopropyltryptamine (MiPT).[1][2] It is the analogue and bioisostere of MiPT in which the indole nitrogen has been replaced with an oxygen atom, making it a benzofuran rather than tryptamine derivative.[1][2] The drug shows affinity for serotonin receptors, including the serotonin 5-HT1A, 5-HT2A, and 5-HT2B receptors (IC50Tooltip half-maximal inhibitory concentration = 5,000 nM, 500 nM, and 800 nM, respectively).[1][2] Its affinities for these receptors were 7-fold, 13-fold, and 1.5-fold lower than those of MiPT, respectively.[1][2] MiPBF was first described in the scientific literature by Dennis McKenna and David Repke and colleagues in 1990.[1][2]

See also

References

  1. ^ a b c d e Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. Bioisosteric replacements of the pyrrole ring have also been reported. For example, the indole core was replaced with the benzofuran scaffold. However, this scaffold provided compounds with significantly reduced binding affinity compared to the tryptamine counterpart (21, Ki = 470 nM; 20, Ki = 36 nM; [125I]R-(−)-DOI) at the 5-HT2AR (Figure 5C).124
  2. ^ a b c d e McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186. Fig. 1. Structures of indolealkylamine derivatives assayed in radioligand competition studies. [...] Table 1. Inhibition constants for tryptamine derivatives [...] The difference in affinities between N-methyl-N-isopropyltryptamine and the benzofuran analog is worth noting; the indole displayed approximately 13- and 7-fold greater affinity at the 5-HT2A and 5-HT1A sites, respectively, than the benzofuran. This indicates that the indolic nitrogen is an important determinant of affinity at these sites. In fact, the importance of the indole nitrogen to the biological activity of the tryptamines has been demonstrated by Winter, Gessner and Godse (1967) and by Pinder, Green and Thompson (1971), in studies in which the indole nitrogen was replaced by oxygen, sulfur or methylene. [...] The difference between the benzofuran and tryptamine derivatives at the 5-HT2B site, however, was less marked.
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