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MedKoo Cat#: 584712 | Name: Doxepin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Doxepin is a dibenzoxepin tricyclic compound that possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.

Chemical Structure

Doxepin
Doxepin
CAS#1668-19-5 (free base)

Theoretical Analysis

MedKoo Cat#: 584712

Name: Doxepin

CAS#: 1668-19-5 (free base)

Chemical Formula: C19H21NO

Exact Mass: 279.1623

Molecular Weight: 279.38

Elemental Analysis: C, 81.68; H, 7.58; N, 5.01; O, 5.73

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
1668-19-5 (free base) 1229-29-4 (HCl)
Synonym
Doxepin; Doxepine; (e)-doxepin; Doxepina; Doxepinum; trans-doxepin
IUPAC/Chemical Name
1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl-
InChi Key
ODQWQRRAPPTVAG-GZTJUZNOSA-N
InChi Code
InChI=1S/C19H21NO/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/b17-11+
SMILES Code
CN(C)CC/C=C1C2=CC=CC=C2OCC3=CC=CC=C/13
Appearance
Solid powder
Purity
>98% (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
Shelf Life
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 279.38 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.

Recalculate based on batch purity %
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
1: Matheson E, Hainer BL. Insomnia: Pharmacologic Therapy. Am Fam Physician. 2017 Jul 1;96(1):29-35. Review. PubMed PMID: 28671376. 2: Edmonds C, Swanoski M. A Review of Suvorexant, Doxepin, Ramelteon, and Tasimelteon for the Treatment of Insomnia in Geriatric Patients. Consult Pharm. 2017 Mar 1;32(3):156-160. doi: 10.4140/TCP.n.2017.156. Review. PubMed PMID: 28270270. 3: Yeung WF, Chung KF, Yung KP, Ng TH. Doxepin for insomnia: a systematic review of randomized placebo-controlled trials. Sleep Med Rev. 2015 Feb;19:75-83. doi: 10.1016/j.smrv.2014.06.001. Epub 2014 Jun 19. Review. PubMed PMID: 25047681. 4: Leenstra JL, Miller RC, Qin R, Martenson JA, Dornfeld KJ, Bearden JD, Puri DR, Stella PJ, Mazurczak MA, Klish MD, Novotny PJ, Foote RL, Loprinzi CL. Doxepin rinse versus placebo in the treatment of acute oral mucositis pain in patients receiving head and neck radiotherapy with or without chemotherapy: a phase III, randomized, double-blind trial (NCCTG-N09C6 [Alliance]). J Clin Oncol. 2014 May 20;32(15):1571-7. doi: 10.1200/JCO.2013.53.2630. Epub 2014 Apr 14. PubMed PMID: 24733799; PubMed Central PMCID: PMC4026580. 5: Laffleur F, Zilio M, Shuwisitkul D. Modified biomolecule as potential vehicle for buccal delivery of doxepin. Ther Deliv. 2016 Oct;7(10):683-689. PubMed PMID: 27790954. 6: Foroutan N, Etminan A, Nikvarz N, Shojai Shahrokh Abadi M. Comparison of pregabalin with doxepin in the management of uremic pruritus: a randomized single blind clinical trial. Hemodial Int. 2017 Jan;21(1):63-71. doi: 10.1111/hdi.12455. Epub 2016 Jul 11. PubMed PMID: 27397522. 7: Unterecker S, Reif A, Hempel S, Proft F, Riederer P, Deckert J, Pfuhlmann B. Interaction of valproic acid and the antidepressant drugs doxepin and venlafaxine: analysis of therapeutic drug monitoring data under naturalistic conditions. Int Clin Psychopharmacol. 2014 Jul;29(4):206-11. doi: 10.1097/YIC.0000000000000025. PubMed PMID: 24374906; PubMed Central PMCID: PMC4047312. 8: Shiroishi M, Kobayashi T. Structural Analysis of the Histamine H(1) Receptor. Handb Exp Pharmacol. 2017;241:21-30. doi: 10.1007/164_2016_10. Review. PubMed PMID: 27826702. 9: Paulzen M, Haen E, Hiemke C, Fay B, Unholzer S, Gründer G, Schoretsanitis G. Antidepressant polypharmacy and the potential of pharmacokinetic interactions: Doxepin but not mirtazapine causes clinically relevant changes in venlafaxine metabolism. J Affect Disord. 2018 Feb;227:506-511. doi: 10.1016/j.jad.2017.11.046. Epub 2017 Nov 13. PubMed PMID: 29156365. 10: Gimeno A, Calpena AC, Sanz R, Mallandrich M, Peraire C, Clares B. Transbuccal delivery of doxepin: studies on permeation and histological investigation. Int J Pharm. 2014 Dec 30;477(1-2):650-4. doi: 10.1016/j.ijpharm.2014.10.060. Epub 2014 Nov 1. PubMed PMID: 25445535. 11: Sanz R, Calpena AC, Mallandrich M, Gimeno Á, Halbaut L, Clares B. Development of a buccal doxepin platform for pain in oral mucositis derived from head and neck cancer treatment. Eur J Pharm Biopharm. 2017 Aug;117:203-211. doi: 10.1016/j.ejpb.2017.04.019. Epub 2017 Apr 21. PubMed PMID: 28438551. 12: Shamsayei M, Yamini Y, Asiabi H. Polythiophene/graphene oxide nanostructured electrodeposited coating for on-line electrochemically controlled in-tube solid-phase microextraction. J Chromatogr A. 2016 Dec 2;1475:8-17. doi: 10.1016/j.chroma.2016.11.003. Epub 2016 Nov 4. PubMed PMID: 27836227. 13: Su YT, Meng XX, Zhang X, Guo YB, Zhang HJ, Cheng YP, Xie XP, Chang YM, Bao JX. Doxepin Mitigates Noise-induced Neuronal Damage in Primary Auditory Cortex of Mice via Suppression of Acid Sphingomyelinase/Ceramide Pathway. Anat Rec (Hoboken). 2017 Dec;300(12):2220-2232. doi: 10.1002/ar.23677. Epub 2017 Aug 28. PubMed PMID: 28806500. 14: Drake CL, Durrence H, Cheng P, Roth T, Pillai V, Peterson EL, Singh M, Tran KM. Arousability and Fall Risk During Forced Awakenings From Nocturnal Sleep Among Healthy Males Following Administration of Zolpidem 10 mg and Doxepin 6 mg: A Randomized, Placebo-Controlled, Four-Way Crossover Trial. Sleep. 2017 Jul 1;40(7). doi: 10.1093/sleep/zsx086. PubMed PMID: 28575467. 15: Fahimirad B, Asghari A, Bazregar M, Rajabi M, Fahimi E. Application of tandem dispersive liquid-liquid microextraction for the determination of doxepin, citalopram, and fluvoxamine in complicated samples. J Sep Sci. 2016 Dec;39(24):4828-4834. doi: 10.1002/jssc.201600673. Epub 2016 Nov 25. PubMed PMID: 27804252. 16: Park HJ, Baik HJ, Kim DY, Lee GY, Woo JH, Zuo Z, Chung RK. Doxepin and imipramine but not fluoxetine reduce the activity of the rat glutamate transporter EAAT3 expressed in Xenopus oocytes. BMC Anesthesiol. 2015 Aug 8;15:116. doi: 10.1186/s12871-015-0098-5. PubMed PMID: 26253075; PubMed Central PMCID: PMC4528682. 17: Rajendiran N, Thulasidhasan J. Spectroscopic, electrochemical and molecular docking studies of dothiepin and doxepin with bovine serum albumin and DNA base. Luminescence. 2016 Dec;31(8):1438-1447. doi: 10.1002/bio.3126. Epub 2016 Mar 17. PubMed PMID: 26991906. 18: Cobanoglu H, Coskun M, Çayir A, Coskun M. In vitro genotoxic and cytotoxic effects of doxepin and escitalopram on human peripheral lymphocytes. Drug Chem Toxicol. 2018 Apr;41(2):238-244. doi: 10.1080/01480545.2017.1365885. Epub 2017 Aug 31. PubMed PMID: 28854817. 19: Neukamm MA, Vogt S, Hermanns-Clausen M, Naue J, Thierauf A, Auwärter V. Fatal doxepin intoxication--suicide or slow gradual intoxication? Forensic Sci Int. 2013 Apr 10;227(1-3):82-4. doi: 10.1016/j.forsciint.2012.08.050. Epub 2012 Sep 19. PubMed PMID: 22999230. 20: Ye Y, Liu C, Liu X, Huang S. Ovariectomy changes the response to antidepressant drugs in tail suspension test in mice. Gynecol Endocrinol. 2016 Dec;32(12):986-990. Epub 2016 Jun 26. PubMed PMID: 27345718.

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