2-BFI hydrochloride - CAS 89196-95-2
Category: Inhibitor
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Molecular Formula:
C11H10N2O.HCl
Molecular Weight:
222.67
COA:
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Targets:
Imidazoline Receptor
Description:
2-BFI hydrochloride is a high affinity I2 ligand (Ki = 9.8 nM) that acts as a putative I2 agonist. 2-BFI potentiates morphine antinociception.
Brife Description:
putative I2 agonist
Related CAS:
72583-92-7 (free base)
Synonyms:
2-(2-Benzofuranyl)-2-imidazoline hydrochloride; 2-(1-benzofuran-2-yl)-4,5-dihydro-1H-imidazole hydrochloride
MSDS:
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InChIKey:
RFNFFVDVGWOSNZ-UHFFFAOYSA-N
InChI:
InChI=1S/C11H10N2O.ClH/c1-2-4-9-8(3-1)7-10(14-9)11-12-5-6-13-11;/h1-4,7H,5-6H2,(H,12,13);1H
Canonical SMILES:
C1CN=C(N1)C2=CC3=CC=CC=C3O2.Cl
1.Neuroanatomical characterization of imidazoline I
Siemian JN;Jia S;Liu JF;Zhang Y;Li JX Eur J Neurosci. 2018 May;47(9):1087-1095. doi: 10.1111/ejn.13899. Epub 2018 Mar 23.
Chronic pain is a significant public health problem with a lack of safe and effective analgesics. The imidazoline I;2; receptor (I;2; R) is a promising analgesic target, but the neuroanatomical structures involved in mediating I;2; R-associated behaviors are unknown. I;2; Rs are enriched in the arcuate nucleus, dorsal raphe (DR), interpeduncular nucleus, lateral mammillary body, medial habenula, nucleus accumbens (NAc) and paraventricular nucleus; thus, this study investigated the antinociceptive and hypothermic effects of microinjections of the I;2; R agonist 2-(2-benzofuranyl)-2-imidazoline hydrochloride (2-BFI). In rats, intra-DR microinjections produced antinociception in complete Freund's adjuvant- and chronic constriction injury-induced pain models. Intra-NAc microinjections produced antinociception and increased noxious stimulus-associated side time in a place escape/avoidance paradigm. Intra-NAc pretreatment with the I;2; R antagonist idazoxan but not the D1 receptor antagonist SCH23390 or the D2 receptor antagonist raclopride attenuated intra-NAc 2-BFI-induced antinociception. Intra-NAc idazoxan did not attenuate systemically administered 2-BFI-induced antinociception. Microinjections into the other regions did not produce antinociception, and in none of the regions produced hypothermia.
2.Computational comparison of imidazoline association with the I2 binding site in human monoamine oxidases.
Basile L;Pappalardo M;Guccione S;Milardi D;Ramsay RR J Chem Inf Model. 2014 Apr 28;54(4):1200-7. doi: 10.1021/ci400346k. Epub 2014 Apr 2.
Imidazoline ligands in I2-type binding sites in the brain alter monoamine turnover and release. One example of an I2 binding site characterized by binding studies, kinetics, and crystal structure has been described in monoamine oxidase B (MAO B). MAO A also binds imidazolines but has a different active site structure. Docking and molecular dynamics were used to explore how 2-(2-benzofuranyl)-2-imidazoline hydrochloride (2-BFI) binds to MAO A and to explain why tranylcypromine increases tight binding to MAO B. The energy for 2-BFI binding to MAO A was comparable to that for tranylcypromine-modified MAO B, but the location of 2-BFI in the MAO A could be anywhere in the monopartite substrate cavity. Binding to the tranylcypromine-modified MAO B was with high affinity and in the entrance cavity as in the crystal structure, but the energies of interaction with the native MAO B were less favorable. Molecular dynamics revealed that the entrance cavity of MAO B after tranylcypromine modification is both smaller and less flexible. This change in the presence of tranylcypromine may be responsible for the greater affinity of tranylcypromine-modified MAO B for imidazoline ligands.
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CAS 89196-95-2 2-BFI hydrochloride

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