An opioid receptor agonist
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Active Metabolite(s)
347503,4,5-Trimethoxybenzoic Acid
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Trimebutine

Item No. 31574

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3,4,5-trimethoxy-benzoic acid, 2-(dimethylamino)-2-phenylbutyl ester
CAS Number
39133-31-8
Synonyms
  • (±)-Trimebutine
Molecular Formula
C22H29NO5
Formula Weight
387.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:8): 0.11 mg/mlDMSO: 1 mg/ml
SMILES
O=C(C1=CC(OC)=C(C(OC)=C1)OC)OCC(C2=CC=CC=C2)(N(C)C)CC
InChi Code
InChI=1S/C22H29NO5/c1-7-22(23(2)3,17-11-9-8-10-12-17)15-28-21(24)16-13-18(25-4)20(27-6)19(14-16)26-5/h8-14H,7,15H2,1-6H3
InChi Key
LORDFXWUHHSAQU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $49

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    10 g

    $93

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    25 g

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    50 g

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    Product Description

    Trimebutine is an opioid receptor agonist.1,2,3 It binds to μ-, δ-, and κ-opioid receptors with Ki values of 0.34, 0.5, and 0.58 μM, respectively, in canine myenteric plexus synaptosomes.2 Trimebutine inhibits twitch contraction and acetylcholine (ACh) release induced by low-frequency electrical stimulation in isolated guinea pig longitudinal muscle with myenteric plexus (LM-MP; EC50s = 0.274 and 0.215 μM, respectively), effects that are inhibited by the opioid receptor antagonists naloxone and MR2266.3 It increases twitch contraction and ACh release induced by high-frequency electrical stimulation in isolated guinea pig LM-MP when used at concentrations of 1 μM or less, but inhibits these effects at 10 μM or more. Trimebutine (30, 100, and 300 μM) decreases the amplitude and frequency of spontaneous contractions in isolated guinea pig colonic smooth muscle strips.4 It also inhibits large conductance calcium-activated potassium (BKCa) and L-type calcium currents in colonic smooth muscle cells in a concentration-dependent manner.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Delvaux, M., and Wingate, D. Trimebutine: Mechanism of action, effects on gastrointestinal function and clinical results. J. Int. Med. Res. 25(5), 225-246 (1997).

    2. Allescher, H.D., Ahmad, S., and Daniel, E.E. Interaction of trimebutine and Jo-1196 (fedotozine) with opioid receptors in the canine ileum. J. Pharmacol. Exp. Ther. 257(2), 836-842 (1991).

    3. Taniyama, K., Sano, I., Taniyama, S., et al. Dual effect of trimebutine on contractility of the guinea pig ileum via the opioid receptors. Gastroenterology 101(6), 1579-1587 (1991).

    4. Tan, W., Zhang, H., Luo, H.-S., et al. Effects of trimebutine maleate on colonic motility through Ca²+-activated K+ channels and L-type Ca²+ channels. Arch. Pharm. Res. 34(6), 979-985 (2011).