An internal standard for the quantification of metoclopramide
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Metoclopramide-d3

Item No. 28885

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-(methoxy-d3)benzamide
CAS Number
1216522-89-2
Molecular Formula
C14H19ClD3N3O2
Formula Weight
302.8
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: slightly solubleMethanol: slightly soluble
SMILES
ClC1=CC(C(NCCN(CC)CC)=O)=C(OC([2H])([2H])[2H])C=C1N
InChi Code
InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)/i3D3
InChi Key
TTWJBBZEZQICBI-HPRDVNIFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

    $127

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    Product Description

    Metoclopramide-d3 is intended for use as an internal standard for the quantification of metoclopramide (Item Nos. 39844 | 23360) by GC- or LC-MS. Metoclopramide is a dual antagonist of the serotonin (5-HT) receptor subtype 5-HT3 and dopamine D2 receptor (IC50s = 308 and 483 nM, respectively).1 It also reversibly inhibits acetylcholinesterase (AChE) isolated from human postmortem caudate nucleus (Kis = 9.3 and 82 μM for competitive and non-competitive inhibition, respectively).2 Oral administration of metoclopramide inhibits emesis induced by the DNA cross-linking agent cisplatin (Item No. 13119) in ferrets (ED50 = 6,170 µg/kg) and the dopamine receptor agonist apomorphine in dogs (ED50 = 0.45 mg/kg).3,1 Metoclopramide also inhibits apomorphine-induced climbing and stereotypy in mice (ED50s = 2.2 and 6.5 mg/kg, respectively).4 Formulations containing metoclopramide have been used in the treatment of gastroesophageal reflux disease (GERD) and diabetic gastroparesis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hirokawa, Y., Harada, H., Yoshikawa, T., et al. Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist. Chem. Pharm. Bull. (Tokyo) 50(7), 941-959 (2002).

    2. Chemnitius, J.M., Haselmeyer, K.H., Gonska, B.D., et al. Indirect parasympathomimetic activity of metoclopramide: Reversible inhibition of cholinesterases from human central nervous system and blood. Pharmacol. Res. 34(1-2), 65-72 (1996).

    3. Youssefyeh, R.D., Campbell, H.F., Klein, S., et al. Development of high-affinity 5-HT3 receptor antagonists. 1. Initial structure-activity relationship of novel benzamides. J. Med. Chem. 35(5), 895-903 (1992).

    4. Altar, C.A., Boyar, W.C., Wasley, A., et al. Dopamine neurochemical profile of atypical antipsychotics resembles that of D-1 antagonists. Naunyn Schmiedebergs Arch. Pharmacol. 338(2), 162-168 (1988).