An internal standard for the quantification of imipramine
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Unlabeled Version(s)
15890Imipramine (hydrochloride)
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Imipramine-d4 (hydrochloride)

Item No. 43809

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-2,4,6,8-d4-5-propanamine, monohydrochloride
CAS Number
61361-33-9
Synonyms
  • Melipramine-d4
Molecular Formula
C19H20D4N2 • HCl
Formula Weight
320.9
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 25 mg/mlPBS (7.2 pH): 0.5 mg/ml
SMILES
CN(C)CCCN1C2=C(C=C([2H])C=C2[2H])CCC3=C1C([2H])=CC([2H])=C3.Cl
InChi Code
InChI=1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H/i3D,4D,10D,11D;
InChi Key
XZZXIYZZBJDEEP-PTAOTMHMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $369

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    Product Description

    Imipramine-d4 is intended for use as an internal standard for the quantification of imipramine (Item No. 15890) by GC- or LC-MS. Imipramine is a first generation tricyclic antidepressant.1 It inhibits serotonin (5-HT) uptake by isolated human platelets by 54 and 79% when used at concentrations of 1 and 4 µg/ml, respectively, and inhibits norepinephrine uptake in rat brain by 63% when administered at a dose of 20 mg/kg.2,3 It also binds to histamine H1, M1 muscarinic acetylcholine, and α1-adrenergic receptors (Kds = 37, 46, and 32 nM, respectively).4 Imipramine (10 and 20 µM) prevents acid sphingomyelinase activation and subsequent ceramide release induced by infection with replication-deficient vesicular stomatitis virus pseudoviral particles (pp-VSV) presenting the severe acute respiratory coronavirus 2 (SARS-CoV-2) spike protein in Vero cells, an effect that can be overcome with exogenous application of C16 ceramide (d18:1/16:0) (Item No. 10681).5 Formulations containing imipramine have been used in the treatment of depression and as an adjunct in the treatment of childhood enuresis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Spencer, P.S. Review of the pharmacology of existing antidepressants. Br. J. Clin. Pharmacol. 4(Suppl 2), 57S-68S (1977).

    2. Yates, C.M., Todrick, A., and Tait, A.C. Effect of imipramine and some analogues on the uptake of 5-hydroxytryptamine by human blood platelets in vitro. J. Pharm. Pharmacol. 16, 460-463 (1964).

    3. Glowinski, J., and Axelrod, J. Inhibition of uptake of tritiated-noradrenaline in the intact rat brain by imipramine and structurally related compounds. Nature 204, 1318-1319 (1964).

    4. Cusack, B., Nelson, A., and Richelson, E. Binding of antidepressants to human brain receptors: Focus on newer generation compounds. Psychopharmacology (Berl.) 114(4), 559-565 (1994).

    5. Carpinteiro, A., Edwards, M.J., Hoffmann, M., et al. Pharmacological inhibition of acid sphingomyelinase prevents uptake of SARS-CoV-2 by epithelial cells. Cell Rep. Med. 1(8), 100142 (2020).