Doxepin

Modify Date: 2024-01-02 12:25:15

Doxepin structure	Common Name	Doxepin
	CAS Number	1668-19-5	Molecular Weight	279.37600
	Density	1.122 g/cm3	Boiling Point	413.3ºC at 760 mmHg
	Molecular Formula	C₁₉H₂₁NO	Melting Point	187-189ºC
	MSDS	N/A	Flash Point	121.3ºC

Use of Doxepin

Doxepin inhibits reuptake of serotonin and norepinephrine as a tricyclic antidepressant. Doxepin has therapeutic effects in atopic dermatitis，chronic urticarial，can improve cognitive processes， protect central nervous system. Doxepin has also been proposed as a protective factor against oxidative stress[1][2][3].

Name	doxepin
Synonym	More Synonyms

Description	Doxepin inhibits reuptake of serotonin and norepinephrine as a tricyclic antidepressant. Doxepin has therapeutic effects in atopic dermatitis，chronic urticarial，can improve cognitive processes， protect central nervous system. Doxepin has also been proposed as a protective factor against oxidative stress[1][2][3].
Related Catalog	Signaling Pathways >> PI3K/Akt/mTOR >> mTOR Signaling Pathways >> PI3K/Akt/mTOR >> PI3K Signaling Pathways >> PI3K/Akt/mTOR >> Akt Research Areas >> Neurological Disease
In Vitro	The protective effect of doxepin is associated with the enhancement of PSD-95 and synapsin 1 expression via PI3K/AKT/mTOR signaling pathway[4]. Western Blot Analysis[4] Cell Line: SH-SY5Y human neuroblastoma cell line Concentration: 10 ng/mL Incubation Time: 2 h Result: Improved the protein expre-ssion levels of PSD-95, synapsin 1 and p-AKT in SH-SY5Y cells, and decreased the protein expression level of p-mTOR in SH-SY5Y cells.
In Vivo	Doxepin (intraperitoneal injection of 1 mg/kg and 5 mg/kg doxepin once a day for 21 days) can protect against the Aβ1-42-induced memory impairment in rats[4]. Animal Model: SD male rats[4] Dosage: 1, 5mg/kg Administration: Doxepin (intraperitoneal injection of 1 mg/kg and 5 mg/kg doxepin once a day for 21 days) Result: Improved the protein expression levels of PSD-95 and synapsin 1 in hippocampus and tem-poral lobe, and decreased the protein expression level of p-AKT in hippocampus and temporal lobe after treatment of 1 mg/kg of doxepin.
References	[1]. AnnemiekVermeeren, et al. Effects of the use of hypnotics on cognition. Progress in brain research vol. 190 (2011): 89-103. [2]. G Hajak, et al. Doxepin in the treatment of primary insomnia: a placebo-controlled, double-blind, polysomnographic study. The Journal of clinical psychiatry vol. 62,6 (2001): 453-63. [3]. Mahsa Gharzi, et al. Effects of different doses of doxepin on passive avoidance learning in rats. Advanced biomedical research vol. 2 66. 30 Jul. 2013. [4]. Jimei Bu, et al. 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.

Density	1.122 g/cm3
Boiling Point	413.3ºC at 760 mmHg
Melting Point	187-189ºC
Molecular Formula	C₁₉H₂₁NO
Molecular Weight	279.37600
Flash Point	121.3ºC
Exact Mass	279.16200
PSA	12.47000
LogP	3.96240
Vapour Pressure	4.87E-07mmHg at 25°C
Index of Refraction	1.5000 (estimate)
Storage condition	Store at RT

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HQ4300000

CHEMICAL NAME :: Dibenz(b,e)oxepin-delta(sup 11(6H)),gamma-propylamine, N,N-dimethyl-

CAS REGISTRY NUMBER :: 1668-19-5

LAST UPDATED :: 199107

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C19-H21-N-O

MOLECULAR WEIGHT :: 279.41

WISWESSER LINE NOTATION :: T C676 BY IO JHJ BU3N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - bronchiectasis

REFERENCE :: CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 10,327,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 147 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 182 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 135 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 79 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 11 mg/kg

TOXIC EFFECTS :: Autonomic Nervous System - parasympatholytic Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 15,863,1965

Hazard Codes	T
Risk Phrases	25
Safety Phrases	36/37/39-45
HS Code	2932999099

11-(3-chloropro...

CAS#:1221-23-4

Dimethylamine

CAS#:124-40-3

~71%

Doxepin

CAS#:1668-19-5

Literature: SOMAXON PHARMACEUTICALS, INC. Patent: WO2008/85567 A1, 2008 ; Location in patent: Page/Page column 23; 24 ;

Doxepin N-Oxide

CAS#:22684-91-9

~93%

Doxepin

CAS#:1668-19-5

Literature: Gowda, Narendra B.; Rao, Gopal Krishna; Ramakrishna, Ramesha A. Tetrahedron Letters, 2010 , vol. 51, # 43 p. 5690 - 5693

Doxepin hydroch...

CAS#:1229-29-4

Doxepin

CAS#:1668-19-5

Literature: US2007/281990 A1, ; Page/Page column 10 ;

Precursor 3
CAS#:124-40-3 Dimethylamine CAS#:22684-91-9 Doxepin N-Oxide CAS#:1229-29-4 Doxepin hydroch...
DownStream 1
CAS#:22684-91-9 Doxepin N-Oxide

HS Code	2932999099
Summary	2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Doxepin hydrochloride,11-(3-dimethylaminopropylidene)-6,11-dihydrodibenz[b,e]oxepinhydrochloride

Doxepin

Use of Doxepin

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Doxepin Biological Activity

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