B4063

Sigma-Aldrich

BIMU8 hydrate

≥98% (HPLC)

Synonym(s):
2,3-Dihydro-N-[(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-3-(1-methylethyl)-2-oxo-1H-benzimidazole-1-carboxamide Hydrochloride (1:1) hydrate
Empirical Formula (Hill Notation):
C19H26N4O2·HCl · xH2O
Molecular Weight:
378.90 (anhydrous basis)
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥98% (HPLC)

storage condition

desiccated

color

off-white to light tan

solubility

H2O: ≥5 mg/mL

storage temp.

2-8°C

InChI

1S/C19H26N4O2.ClH.H2O/c1-12(2)22-16-6-4-5-7-17(16)23(19(22)25)18(24)20-13-10-14-8-9-15(11-13)21(14)3;;/h4-7,12-15H,8-11H2,1-3H3,(H,20,24);1H;1H2/t13-,14+,15-;;

InChI key

HZJJVFOOACXPTH-XZAJHMFNSA-N

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

BIMU8 hydrate is a potent 5-HT4 serotonin receptor agonist. Serotonin (5-HT) is a major neurotransmitter that acts through a family of GPCRs and one ion channel. 5-HT4 receptor is GPCR expressed in many tissues, including brain, and modulates dopamine secretion, learning, and memory. BIMU8 is a full agonist at 5-HT4, but it binds differently than the endogenous ligand, 5-HT, shown through site-directed mutagenesis studies. It depolarizes neurons and was used to localize 5-HT4 to somatic but not dendritic regions of CA1 pyramidal neurons.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
A Dumuis et al.
Naunyn-Schmiedeberg's archives of pharmacology, 345(3), 264-269 (1992-03-01)
Three chemical classes of serotonin 5-HT4 receptor agonists have been identified so far: 5-substituted indoles (e.g. 5-HT), benzamides (e.g. renzapride) and benzimidazolones (e.g. BIMU 8). In a search for 5-HT4 receptor antagonists, we have discovered that the benzimidazolone derivative DAU...
V Contesse et al.
European journal of pharmacology, 265(1-2), 27-33 (1994-11-14)
We have previously shown that serotonin (5-hydroxytryptamine, 5-HT) stimulate corticosterone and aldosterone secretion from perifused frog adrenal gland in vitro through activation of 5-HT4 receptors. In the present study, we have used this model to investigate the effect of newly...
J K Weatherspoon et al.
European journal of pharmacology, 326(2-3), 133-138 (1997-05-20)
The binding profile of the sigma2 receptor ligand endo-N-(8-methyl-8-azabicyclo[3.2.1.]oct-3-yl)-2,3-dihydro-(1-methyl)eth yl-2-oxo-1H-benzimidazole-1-carboxamidehydrochloride (BIMU-8) had previously been determined, but its agonist/antagonist status at sigma2 receptors had not been identified. We therefore investigated the effects of BIMU-8 for its ability to regulate the stimulated...
A Dumuis et al.
Naunyn-Schmiedeberg's archives of pharmacology, 343(3), 245-251 (1991-03-01)
Recent experimental evidence indicates that central 5-HT4 receptors which are positively coupled to adenylate cyclase, are stimulated by a family of 2-methoxy-4-amino-5-chloro substituted benzamide derivatives. These compounds are also potent stimulants of the gastro-intestinal motility. In this study the ability...
G S Baxter et al.
European journal of pharmacology, 212(2-3), 225-229 (1992-03-03)
Three benzimidazolone derivatives have been evaluated in the tunica muscularis mucosae preparation of the rat oesophagus for activity at the 5-HT4 receptor. BIMU 1 (endo-N-(8-methyl-8-azabicyclo-[3.2.1]oct-3-yl)-2,3-dihydro-3-ethyl-2-ox o- 1H-benzimidazole-1-carboxamide HCl) and BIMU 8 (endo-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-2,3-dihydro-(1-methyl)eth yl- 2-oxo-1H-benzimidazole-1-carboxamide HCl) acted as potent but partial...

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