An inactive metabolite of meclizine and chlorcyclizine
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1-(4-Chlorobenzhydryl)piperazine

Item No. 34518

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(4-chlorophenyl)phenylmethyl]-piperazine
CAS Number
303-26-4
Synonyms
  • N-(p-Chlorobenzhydryl)-piperazine
  • Norchlorcyclizine
  • NSC 86164
Molecular Formula
C17H19ClN2
Formula Weight
286.8
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.2 mg/mlEthanol: 25 mg/ml
λmax
231 nm
SMILES
ClC1=CC=C(C(N2CCNCC2)C3=CC=CC=C3)C=C1
InChi Code
InChI=1S/C17H19ClN2/c18-16-8-6-15(7-9-16)17(14-4-2-1-3-5-14)20-12-10-19-11-13-20/h1-9,17,19H,10-13H2
InChi Key
UZKBSZSTDQSMDR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

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    Product Description

    1-(4-Chlorobenzhydryl)piperazine is an inactive metabolite of meclizine (Item No. 14615) and chlorcyclizine (Item No. 19239).1,2 It has also been found as an impurity in commercial preparations of hydroxyzine (Item No. 24039) and cetirizine (Item No. 19686).3,4 1-(4-Chlorobenzhydryl)piperazine has been used in the synthesis of voltage-gated sodium channel 1.7 (Nav1.7) inhibitors, anticancer agents, and antihistamines.5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gaertner, H.J., Breyer, U., and Liomin, G. Chronic administration of chlorcyclizine and meclizine to rats: Accumulation of a metabolite formed by piperazine ring cleavage. J. Pharmacol. Exp. Ther. 185(2), 195-201 (1973).

    2. Kuntzman, R., Klutch, A., Tsai, I., et al. Physiological distribution and metabolic inactivation of chlorcyclizine and cyclizine. J. Pharmacol. Exp. Ther. 149(1), 29-35 (1965).

    3. Simpson, D., Skellern, G.G., and Miller, J.H. Method for the control of known impurities in hydroxyzine hydrochloride. J. Pharm. Biomed. Anal. 14(8-10), 1371-1375 (1996).

    4. Javid, F.S., Shafaat, A., and Zarghi, A. Determination of cetirizine and its impurities in bulk and tablet formulation using a validated capillary zone electrophoretic method. J. Anal. Chem. 69(5), 442-447 (2014).

    5. Back, S.K., Kam, Y.L., Oh, J.A., et al. Synthesis and evaluation of (4-chlorobenzhydryl) piperazine amides as sodium channel Nav1.7 inhibitors. Bull. Korean Chem. Soc. 36(9), 2290-2297 (2015).

    6. Yarim, M., Koksal, M., Durmaz, I., et al. Cancer cell cytotoxicities of 1-(4-substitutedbenzoyl)-4-(4-chlorobenzhydryl)piperazine derivatives. Int. J. Mol. Sci. 13(7), 8071-8085 (2012).

    7. Narsaiah, A.V., and Narssimha, P. Efficient synthesis of antihistamines clocinizine and chlorcyclizine. Med. Chem. Res. 21, 538–541 (2012).