An internal standard for the quantification of N-desmethylclozapine
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Unlabeled Version(s)
26153N-Desmethylclozapine
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N-Desmethylclozapine-d8

Item No. 26027

Technical Information
Formal Name
8-chloro-11-(piperazin-1-yl-2,2,3,3,5,5,6,6-d8)-5H-dibenzo[b,e][1,4]diazepine
CAS Number
1189888-77-4
Synonyms
  • Norclozapine-d8
Molecular Formula
C17H9ClD8N4
Formula Weight
Purity
≥99% deuterated forms (d1-d8)
A solid
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
229, 260, 297 nm
SMILES
ClC(C=C1)=CC2=C1NC(C=CC=C3)=C3C(N4C([2H])([2H])C([2H])([2H])NC([2H])([2H])C4([2H])[2H])=N2
InChi Code
InChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2/i7D2,8D2,9D2,10D2
InChi Key
JNNOSTQEZICQQP-UFBJYANTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    N-Desmethylclozapine-d8 is intended for use as an internal standard for the quantification of N-desmethylclozapine by GC- or LC-MS. N-Desmethylclozapine is an active metabolite of the atypical antipsychotic clozapine (Item Nos. 12059 | 25779).1 It was originally described as an antagonist of serotonin (5-HT) receptor subtype 5-HT2C (IC50 = 7.1 nM in rat choroid plexus) and later as an inverse agonist using human recombinant receptors.2,3 N-Desmethylclozapine is an antagonist at dopamine D4 receptors, an agonist at δ-opioid receptors, and a partial agonist at dopamine D2 and D3, M1 muscarinic acetylcholine, and 5-HT1A receptors.3,1,4 N-Desmethylclozapine (30 mg/kg) decreases exploratory locomotor activity and increases prepulse inhibiton of the acoustic startle response in mice.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Burstein, E.S., Ma, J., Wong, S., et alIntrinsic efficacy of antipsychotics at human D2, D3, and D4 dopamine receptors: Identification of the clozapine metabolite N-desmethylclozapine as a D2/D3 partial agonist. J. Pharmacol. Exp. Ther. 315(3), 1278-1287 (2005).

    2. Kuoppamäki, M., Syvälahti, E., and Hietala, J. Clozapine and N-desmethylclozapine are potent 5-HT1C receptor antagonists. Eur. J. Pharmacol. 245(2), 179-182 (1993).

    3. Lameh, J., Burstein, E.S., Taylor, E., et alPharmacology of N-desmethylclozapine. Pharmacol. Ther. 115(2), 223-231 (2007).

    4. Odagaki, Y., Kinoshita, M., and Ota, T. Comparative analysis of pharmacological properties of xanomeline and N-desmethylclozapine in rat brain membranes. J. Psychopharmacol. 30(9), 896-912 (2016).

    5. Maehara, S., Hikichi, H., and Ohta, H. Behavioral effects of N-desmethylclozapine on locomotor activity and sensorimotor gating function in mice-Possible involvement of muscarinic receptors. Brain Res. 1418, 111-119 (2011).