A tricyclic antidepressant
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Doxepin (hydrochloride)

Item No. 15888

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(dibenz[b,e]oxepin-11(6H)-ylidene)-N,N-dimethyl-1-propanamine, monohydrochloride
CAS Number
1229-29-4
Molecular Formula
C19H21NO • HCl
Formula Weight
315.8
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
296 nm
SMILES
CN(C)CC/C=C1C2=C(C=CC=C2)COC3=C/1C=CC=C3.Cl
InChi Code
InChI=1S/C19H21NO.ClH/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19;/h3-6,8-12H,7,13-14H2,1-2H3;1H/b17-11-;
InChi Key
MHNSPTUQQIYJOT-CULRIWENSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $41

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    5 g

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    Product Description

    Doxepin is a tricyclic antidepressant that binds to the serotonin (5-HT) transporter (SERT) and norepinephrine transporter (NET; Kds = 68 and 29.5 nM, respectively).1 It is a histamine H1 receptor antagonist (Ki = 1.23 nM).2 Doxepin selectively binds to SERT and NET over the dopamine transporter (DAT; Kd = 12,100 nM) and inhibits histamine H1 over H2, H3, and H4 receptors (Kis = 170, 39,810, and 15,135 nM, respectively).1,2 It also binds to the 5-HT2 receptor, as well as to muscarinic acetylcholine and α1-adrenergic receptors (α1-ARs; Kds = 27, 23, and 23.5 nM, respectively).3 Doxepin (10 mg/kg, i.p.) decreases allodynia and hyperalgesia in a mouse model of chronic constriction injury-induced neuropathic pain.4 It increases the distance traveled in the center of the open field test and reduces immobility time in the forced swim test in a mouse model of depression induced by chronic stress when administered orally at a dose of 15 mg/kg.5 Formulations containing doxepin have been used in the treatment of depression and insomnia.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Appl, H., Holzammer, T., Dove, S., et al. Interactions of recombinant human histamine H1, H2, H3, and H4 receptors with 34 antidepressants and antipsychotics. Naunyn-Schmiedebergs Arch. Pharmacol. 385(2), 145-170 (2012).

    3. 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).

    4. Mika, J., Jurga, A.M., Starnowska, J., et al. Effects of chronic doxepin and amitriptyline administration in naïve mice and in neuropathic pain mice model. Neuroscience 294, 38-50 (2015).

    5. Kim, Y.R., Park, B.-K., Kim, Y.H., et al. Antidepressant effect of Fraxinus rhynchophylla Hance extract in a mouse model of chronic stress-induced depression. BioMed. Res. Int. 8249563 (2018).