Synonym
Doxepin HCl; (e)-doxepin hydrochloride; Adapin; Doxepine hydrochloride; Novoxapin hydrochloride
IUPAC/Chemical Name
(3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine;hydrochloride
InChi Key
MHNSPTUQQIYJOT-SJDTYFKWSA-N
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+;
SMILES Code
CN(C)CC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31.Cl
Appearance
White to off-white crystalline powder.
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Doxepin hydrochloride is a potent and selective histamine receptor H1 antagonist.
In vitro activity:
As shown in the present study, doxepin significantly diminished the stimulatory effect of GPVI agonist collagen-related peptide (CRP) on intracellular Ca2+ release as well as subsequent extracellular Ca2+ influx. Doxepin was partially effective by impairment of CRP-dependent IP3 production. Moreover, doxepin abrogated CRP-induced platelet degranulation and integrin αIIbβ3 activation and aggregation. Finally, doxepin markedly blunted in vitro platelet adhesion to collagen and thrombus formation under high arterial shear rates (1,700-s).
Reference: Iran J Basic Med Sci. 2017 Sep;20(9):1044-1049. https://pubmed.ncbi.nlm.nih.gov/29085600/
In vivo activity:
Administration of Doxepin considerably increased the step through latencies in the rats that received the doses of 1 and 5 mg/kg (P < 0.05). These results indicate that Doxepin has desirable effects on cognitive functions in low doses. Therefore, Doxepin can be considered as memory enhancers that understanding the underling mechanisms need further investigation.
Reference: Adv Biomed Res. 2013 Jul 30;2:66. https://pubmed.ncbi.nlm.nih.gov/24223381/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
20.0 |
63.32 |
| DMSO |
62.7 |
198.41 |
| Ethanol |
46.5 |
147.23 |
| PBS (pH 7.2) |
10.0 |
0.32 |
| Water |
56.5 |
178.89 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
315.84
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Geue S, Walker-Allgaier B, Eißler D, Tegtmeyer R, Schaub M, Lang F, Gawaz M, Borst O, Münzer P. Doxepin inhibits GPVI-dependent platelet Ca2+ signaling and collagen-dependent thrombus formation. Am J Physiol Cell Physiol. 2017 Jun 1;312(6):C765-C774. doi: 10.1152/ajpcell.00262.2016. Epub 2017 Apr 12. PMID: 28404545.
2. Cusack B, Nelson A, Richelson E. Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. doi: 10.1007/BF02244985. PMID: 7855217.
3. Bu J, Zu H. Mechanism underlying the effects of doxepin on β-amyloid -induced memory impairment in rats. Iran J Basic Med Sci. 2017 Sep;20(9):1044-1049. doi: 10.22038/IJBMS.2017.9274. PMID: 29085600; PMCID: PMC5651458.
4. Gharzi M, Dolatabadi HR, Reisi P, Javanmard SH. Effects of different doses of doxepin on passive avoidance learning in rats. Adv Biomed Res. 2013 Jul 30;2:66. doi: 10.4103/2277-9175.115823. PMID: 24223381; PMCID: PMC3814585.
In vitro protocol:
1. Geue S, Walker-Allgaier B, Eißler D, Tegtmeyer R, Schaub M, Lang F, Gawaz M, Borst O, Münzer P. Doxepin inhibits GPVI-dependent platelet Ca2+ signaling and collagen-dependent thrombus formation. Am J Physiol Cell Physiol. 2017 Jun 1;312(6):C765-C774. doi: 10.1152/ajpcell.00262.2016. Epub 2017 Apr 12. PMID: 28404545.
2. Cusack B, Nelson A, Richelson E. Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. doi: 10.1007/BF02244985. PMID: 7855217.
In vivo protocol:
1. Bu J, Zu H. Mechanism underlying the effects of doxepin on β-amyloid -induced memory impairment in rats. Iran J Basic Med Sci. 2017 Sep;20(9):1044-1049. doi: 10.22038/IJBMS.2017.9274. PMID: 29085600; PMCID: PMC5651458.
2. Gharzi M, Dolatabadi HR, Reisi P, Javanmard SH. Effects of different doses of doxepin on passive avoidance learning in rats. Adv Biomed Res. 2013 Jul 30;2:66. doi: 10.4103/2277-9175.115823. PMID: 24223381; PMCID: PMC3814585.
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determination of doxepin hydrochloride in commercial dosage forms. AAPS
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21. PubMed PMID: 19936937; PubMed Central PMCID: PMC2799607.
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hydrochloride and fast green and its application]. Guang Pu Xue Yu Guang Pu Fen
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4: Kandagal PB, Seetharamappa J, Ashoka S, Shaikh SM, Manjunatha DH. Study of the
interaction between doxepin hydrochloride and bovine serum albumin by
spectroscopic techniques. Int J Biol Macromol. 2006 Nov 15;39(4-5):234-9. Epub
2006 Apr 1. PubMed PMID: 16678251.
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doxepin hydrochloride in pharmaceutical preparations using titanium (IV) and iron
(III) thiocyanate complexes. Farmaco. 2005 Jan;60(1):61-9. Epub 2004 Dec 19.
PubMed PMID: 15652371.
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Jan;33(1):88-9. PubMed PMID: 11879844.
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combination of both produces analgesia in chronic human neuropathic pain: a
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dermatitis caused by doxepin hydrochloride cream. J Am Acad Dermatol. 1996
Jan;34(1):143-4. PubMed PMID: 8543684.
9: Whall TJ, Dokladalova J. High-performance liquid chromatographic determination
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Nov;68(11):1454-6. PubMed PMID: 512900.
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PubMed PMID: 4604347.
11: Watanabe S, Morimoto Y, Ueki S. [Electroencephalographic effects of doxepin
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PMID: 4676617.
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Yakurigaku Zasshi. 1972 Nov;68(6):762-99. Japanese. PubMed PMID: 4676615.
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effects of doxepin hydrochloride]. Nihon Yakurigaku Zasshi. 1972
Nov;68(6):716-61. Japanese. PubMed PMID: 4676614.
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thymoanaleptic agent]. Nouv Presse Med. 1972 Jun 17;1(25):1717-8. French. PubMed
PMID: 5041723.
15: Dobkin AB, Desai AA. Double-blind evaluation of doxepin hydrochloride
(Sinequan) for preanaesthetic medication. Can Anaesth Soc J. 1972
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16: Naftulin DH, Ware JE Jr. A behavioral and clinical evaluation of two
psychotropic agents: doxepin-hydrochloride and perphenazine-amitriptylin
hydrochloride. Psychosomatics. 1972 Mar-Apr;13(2):125-30. PubMed PMID: 4603988.
17: Saito S, Jinnai K, Ikemura K. [Use of Sinequan (doxepin hydrochloride) in
urology]. Hinyokika Kiyo. 1972 Feb;18(2):101-4. Japanese. PubMed PMID: 5064088.
18: Evaluation of doxepin hydrochloride (Sinequan). JAMA. 1971 Mar
22;215(12):1967-8. PubMed PMID: 4993965.
19: Montgomery BA, Cullinan TR, Bayley AJ. A double-blind comparative trial of
doxepin hydrochloride and chlordiazepoxide in anxiety and depression in general
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