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MiPBF

From Wikipedia, the free encyclopedia

Pharmaceutical compound
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
PubChemCID
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 asN-methyl-N-isopropyl-3-(2-aminoethyl)benzofuran or as1-oxa-N-methyl-N-isopropyltryptamine (1-oxa-MiPT), is aserotonin receptor modulator of thebenzofuran family related to thepsychedelictryptaminemethylisopropyltryptamine (MiPT).[1][2] It is theanalogue andbioisostere of MiPT in which theindolenitrogen has been replaced with anoxygenatom, making it a benzofuran rather than tryptaminederivative.[1][2] The drug showsaffinity forserotonin receptors, including theserotonin5-HT1A,5-HT2A, and5-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 thescientific literature byDennis McKenna andDavid Repke and colleagues in 1990.[1][2]

See also

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References

[edit]
  1. ^abcdeDuan 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. ^abcdeMcKenna 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.

External links

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5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
α-Ketotryptamines
Cyclized tryptamines
Isotryptamines
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