An internal standard for the quantification of prochlorperazine
Related Products
Unlabeled Version(s)
20742Prochlorperazine (maleate)
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Prochlorperazine-d8 (hydrochloride)

Item No. 31916

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-chloro-10-[3-(4-methyl-1-piperazinyl-d8)propyl]-10H-phenothiazine, dihydrochloride
CAS Number
2930627-64-6
Molecular Formula
C20H16ClD8N3S • 2HCl
Formula Weight
454.9
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
CN1C([2H])([2H])C([2H])([2H])N(CCCN2C(C=CC=C3)=C3SC4=C2C=C(Cl)C=C4)C([2H])([2H])C1([2H])[2H].Cl.Cl
InChi Code
InChI=1S/C20H24ClN3S.2ClH/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24;;/h2-3,5-8,15H,4,9-14H2,1H3;2*1H/i11D2,12D2,13D2,14D2;;
InChi Key
FVKRDYKLIRFKLL-ZWKVGDSCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Prochlorperazine-d8 is intended for use as an internal standard for the quantification of prochlorperazine (Item No. 20742) by GC- or LC-MS. Prochlorperazine is a dopamine D2 receptor antagonist with Ki values of 4.7 and 2.9 nM for rat recombinant D2 receptors in CHO cells and rat striatal membranes, respectively.1,2 It also binds to rat recombinant D3 receptors expressed in CHO cells (Ki = 35 nM) and to the serotonin (5-HT) receptor subtype 5-HT3 in N1E-115 mouse neuroblastoma cell membranes (Ki = 1,200 nM).1,3 Prochlorperazine (2 mg/kg) increases the latency to paw licking in a hot plate test, indicating analgesia, an effect that is blocked by antisense oligonucleotides against the M1 muscarinic receptor.4 It also inhibits emesis induced by apomorphine (Item No. 16094) in dogs (ED50 = 0.34 mg/kg).5 Formulations containing prochlorperazine have been used in the treatment of psychotic disorders and as antiemetics.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sokoloff, P., Giros, B., Martres, M.P., et al. Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics. Nature 137(6289), 146-151 (1990).

    2. Tsuchihashi, H., Sasaki, T., Kojima, S., et al. Binding of [3H]haloperidol to dopamine D2 receptors in the rat striatum. J. Pharm. Pharmacol. 44(11), 911-914 (1992).

    3. Lummis, S.C., and Baker, J. Radioligand binding and photoaffinity labelling studies show a direct interaction of phenothiazines at 5-HT3 receptors. Neuropharmacology 36(4-5), 665-670 (1997).

    4. Ghelardini, C., Galeotti, N., Uslenghi, C., et al. Prochlorperazine induces central antinociception mediated by the muscarinic system. Pharmacol. Res. 50(3), 351-358 (2004).

    5. Niemegeers, C.J.E. Antiemetic specificity of dopamine antagonists. Psychopharmacology (Berl.) 78(3), 210-213 (1982).