An internal standard for the quantification of maprotiline
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Unlabeled Version(s)
15892Maprotiline (hydrochloride)
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Maprotiline-d3 (hydrochloride)

Item No. 33301

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-methyl-d3-9,10-ethanoanthracene-9(10H)-propanamine, monohydrochloride
CAS Number
1329496-63-0
Synonyms
  • Ba 34276-d3
Molecular Formula
C20H20D3N • HCl
Formula Weight
316.9
Purity
≥99% deuterated forms (d1-d3)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
SMILES
[2H]C([2H])([2H])NCCCC1(CC2)C3=CC=CC=C3C2C4=C1C=CC=C4.Cl
InChi Code
InChI=1S/C20H23N.ClH/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20;/h2-5,7-10,15,21H,6,11-14H2,1H3;1H/i1D3;
InChi Key
NZDMFGKECODQRY-NIIDSAIPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Maprotiline-d3 is intended for use as an internal standard for the quantification of maprotiline (Item No. 15892) by GC- or LC-MS. Maprotiline is a tricyclic antidepressant.1,2 It binds to the norepinephrine transporter (NET; Kd = 11 nM) and is selective for NET over the serotonin (5-HT) and dopamine transporters (Kds = 5,800 and 1,000 nM, respectively).2 Maprotiline also binds to the 5-HT receptor subtype 5-HT2A (Ki = 51 nM), as well as histamine H1, muscarinic acetylcholine, α1-adrenergic, and dopamine D2 receptors (Kds = 2, 570, 90, and 350 nM, respectively).3 In vivo, maprotiline inhibits norepinephrine reuptake in rat brain and peripheral tissues.4 It reduces isolation-induced aggressive behavior and inhibits electrical foot-shock stimulation-induced belligerence in mice when administered at doses ranging from 3 to 10 mg/kg. Maprotiline (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 (Item No. 10681).5 Formulations containing maprotiline have been used in the treatment of depression and anxiety. This product is also available as an analytical reference material (Item Nos. 32702 | 33077).

    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. Tatsumi, M., Groshan, K., Blakely, R.D., et al. Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur. J. Pharmacol. 340(2-3), 249-258 (1997).

    3. Richelson, E., and Nelson, A. Antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro. J. Pharmacol. Exp. Ther. 230(1), 94-102 (1984).

    4. Pinder, R.M., Brogden, R.N., Speight, T.M., et al. Maprotiline: A review of its pharmacological properties and therapeutic efficacy in mental depressive states. Drugs 13(5), 321-352 (1977).

    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).