| Field | Specification |
|---|---|
| Target | |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C22H29NO5 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Trimebutine is a multi-target inhibitor and opioid receptor agonist with antimuscarinic activity. It inhibits L-type Ca2+ channels and large-conductance calcium-activated potassium channels (BKCa channels), thereby reducing extracellular calcium influx and potassium ion efflux. It also targets Toll-like receptors, inhibiting Toll-like receptor 2/4/7/8/9 signals and blocking LPS-induced IRAK1 activation as well as ERK1/2, JNK and NF-κB activation, thereby exerting anti-inflammatory effects. It induces tumor cell apoptosis by inhibiting the AKT/ERK pathway and inhibits excessive contraction of smooth muscle, and can be used in the study of gastrointestinal disorders such as irritable bowel syndrome (IBS)[1][2][3][4][5][6]. It is supplied as a white to off-white solid (C22H29NO5, MW 387.47) at 99.42% purity.
Physical & Chemical Properties
| CAS Number | 39133-31-8 |
|---|---|
| Molecular Formula | C22H29NO5 |
| Molecular Weight | 387.47 g/mol |
| Purity | 99.42% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | O=C(OCC(C1=CC=CC=C1)(N(C)C)CC)C2=CC(OC)=C(OC)C(OC)=C2 |
| Target | μ Opioid Receptor/MOR, L-type calcium channel, IRAK-1, ERK1, ERK2 |
| Signaling Pathway | GPCR/G Protein; Membrane Transporter/Ion Channel; NF-κB; Immunology/Inflammation; Stem Cell/Wnt; Apoptosis; Neuronal Signaling; MAPK/ERK Pathway; PI3K/Akt/mTOR |
| Solubility | In Vitro: DMSO: 100 mg/mL (258.08 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | 4°C, protect from light. In solvent: -80°C, 6 months; -20°C, 1 month (protect from light). |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (258.08 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 6 months) or -20°C (up to 1 month); protect from light; avoid repeated freeze-thaw cycles.
Data provided by the manufacturer.
In Vitro
Trimebutine (0-1000 μM; 48 h) significantly lowers viability in SHG44, U251, and U-87 MG glioma cells, with IC50 values of 98.28 μM, 128.27 μM, and 204.06 μM, respectively, while showing low toxicity toward normal HEB cells[1]. Trimebutine (0-200 μM; 24-72 h) suppresses U-87 MG cell migration in a concentration- and time-dependent manner[1]. In glioma cells, Trimebutine (0-200 μM; 48-72 h) induces apoptosis, with Bcl-2 downregulation, Bax upregulation, and Caspase-3 activation, and inhibits phosphorylation of AKT (Ser473) and ERK (Thr202/Tyr204)[1].
Cell Viability Assay[1]
| Cell Line | SHG44, U251, U-87 MG |
|---|---|
| Concentration | 0, 10, 50, 100, 200 μM |
| Incubation Time | 48 h and 72 h |
| Result | Reduced phosphorylated AKT (Ser473) and ERK (Thr202/Tyr204) levels in a dose-dependent manner at both time points, while total AKT and ERK protein levels remained unchanged. The inhibition was more pronounced at 72 h for higher concentrations (100-200 μM). |
In Vivo
In a subcutaneous xenograft model of U-87 MG glioma in female nude mice, Trimebutine (100 mg/kg/day; intraperitoneal injection; once a day; 7 days) suppresses tumor growth, raises the number of TUNEL-positive apoptotic cells in tumor tissues, downregulates Bcl-2, upregulates Bax, and inhibits p-AKT and p-ERK signaling pathways[1]. In the colorectal distension model in male mice, Trimebutine (50 mg/kg; oral; single dose) significantly lowers the pain response at 60 mmHg pressure 4 hours after treatment, and shows a weaker overall effect than GIC-1001 at an equimolar dose[2].
- Animal Model:
- Dosage:
- Administration:
- Result: Animal Model: Female nude mice (4-week-old), subcutaneous U-87 MG glioblastoma xenograft model[1] Dosage (solvent): 100 mg/kg/day (DMSO) Administration: Intraperitoneal injection (i.p.), once daily for 7 days, starting when tumors reached ~2 mm3; monitored at days 7, 10, 14, 16, 18, 21. Result: Significantly reduced tumor volume compared to the vehicle control group, with final tumor weight decreasing by ~30%. Histological analysis showed increased TUNEL-positive apoptotic cells in tumor sections. Downregulated Bcl-2 and upregulated Bax protein levels, along with reduced phosphorylation of AKT (Ser473) and ERK (Thr202/Tyr204), indicating modulation of apoptotic and proliferative signaling pathways. No significant toxicity was observed in treated mice, as body weight and general activity remained comparable to controls.
| Animal Model | Female nude mice (4-week-old), subcutaneous U-87 MG glioblastoma xenograft model[1] |
|---|---|
| Dosage | 100 mg/kg/day |
| Administration | Intraperitoneal injection (i.p.), once daily for 7 days, starting when tumors reached ~2 mm3; monitored at days 7, 10, 14, 16, 18, 21. |
| Result | Significantly reduced tumor volume compared to the vehicle control group, with final tumor weight decreasing by ~30%. Histological analysis showed increased TUNEL-positive apoptotic cells in tumor sections. Downregulated Bcl-2 and upregulated Bax protein levels, along with reduced phosphorylation of AKT (Ser473) and ERK (Thr202/Tyr204), indicating modulation of apoptotic and proliferative signaling pathways. No significant toxicity was observed in treated mice, as body weight and general activity remained comparable to controls. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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