2-[(2-ethoxyphenoxy)methyl]morpholine

Modify Date: 2025-08-20 02:55:13

2-[(2-ethoxyphenoxy)methyl]morpholine Structure
2-[(2-ethoxyphenoxy)methyl]morpholine structure
 Common Name 2-[(2-ethoxyphenoxy)methyl]morpholine
CAS Number 46817-91-8 Molecular Weight 237.29500
Density 1.061 g/cm3 Boiling Point 350.5ºC at 760 mmHg
Molecular Formula C13H19NO3 Melting Point 185-186ºC
MSDS N/A Flash Point 144.3ºC

 Use of 2-[(2-ethoxyphenoxy)methyl]morpholine


Viloxazine (Viloxazin) is a norepinephrine reuptake inhibitor, also a potent 5-HT2C agonist and 5-HT2B antagonist with an EC50 of 32 μM and an IC50 of 27 μM for 5-HT2C and 5-HT2B, respectively. The mechanism of action of Viloxazine predominantly involves serotonergic and noradrenergic pathways. Viloxazine can be used for researching depression[1][2].

 Names

Name 2-[(2-ethoxyphenoxy)methyl]morpholine
Synonym More Synonyms

 2-[(2-ethoxyphenoxy)methyl]morpholine Biological Activity

Description Viloxazine (Viloxazin) is a norepinephrine reuptake inhibitor, also a potent 5-HT2C agonist and 5-HT2B antagonist with an EC50 of 32 μM and an IC50 of 27 μM for 5-HT2C and 5-HT2B, respectively. The mechanism of action of Viloxazine predominantly involves serotonergic and noradrenergic pathways. Viloxazine can be used for researching depression[1][2].
Related Catalog
Target

Human 5-HT2C Receptor:32 μM (EC50)

human 5-HT2B Receptor:27 μM (IC50)

References

[1]. Yu C, et al. New Insights into the Mechanism of Action of Viloxazine: Serotonin and Norepinephrine Modulating Properties. J Exp Pharmacol. 2020 Aug 25;12:285-300.

[2]. Pinder RM, et al. Viloxazine: a review of its pharmacological properties and therapeutic efficacy in depressive illness. Drugs. 1977 Jun;13(6):401-21.

 Chemical & Physical Properties

Density 1.061 g/cm3
Boiling Point 350.5ºC at 760 mmHg
Melting Point 185-186ºC
Molecular Formula C13H19NO3
Molecular Weight 237.29500
Flash Point 144.3ºC
Exact Mass 237.13600
PSA 39.72000
LogP 1.78130
Index of Refraction 1.499

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QE3940000
CHEMICAL NAME :
Morpholine, 2-((2-ethoxyphenoxy)methyl)-
CAS REGISTRY NUMBER :
46817-91-8
LAST UPDATED :
199403
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C13-H19-N-O3
MOLECULAR WEIGHT :
237.33
WISWESSER LINE NOTATION :
T6M DOTJ C1OR BO2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity
REFERENCE :
HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity
REFERENCE :
HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
552 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 27,437,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Behavioral - muscle weakness Behavioral - ataxia Behavioral - muscle contraction or spasticity
REFERENCE :
HEPHD2 Handbook of Experimental Pharmacology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.50- 1978- Volume(issue)/page/year: 55,527,1980 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
130 mg/kg
SEX/DURATION :
female 8-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral
REFERENCE :
ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) No.1- 1978- Volume(issue)/page/year: 7,504,1984

 Synthetic Route

(+/-)-4-benzyl-2-(2-ethoxyphenoxymethyl)morpholine structure

(+/-)-4-benzyl-...

CAS#:47374-79-8

~98%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Audouze, Karine; Nielsen, Elsebet stergaard.; Peters, Dan Journal of Medicinal Chemistry, 2004 , vol. 47, # 12 p. 3089 - 3104
2-[(2-ethoxyphenoxy)methyl]morpholine hydrochloride structure

2-[(2-ethoxyphe...

CAS#:35604-67-2

~%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Supernus Pharmaceuticals Inc. Patent: US2011/251198 A1, 2011 ; Location in patent: Page/Page column 15 ;
2-Ethoxyphenol structure

2-Ethoxyphenol

CAS#:94-71-3

~%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Audouze, Karine; Nielsen, Elsebet stergaard.; Peters, Dan Journal of Medicinal Chemistry, 2004 , vol. 47, # 12 p. 3089 - 3104
4-Benzyl-2-(chloromethyl)morpholine structure

4-Benzyl-2-(chl...

CAS#:40987-25-5

~%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Audouze, Karine; Nielsen, Elsebet stergaard.; Peters, Dan Journal of Medicinal Chemistry, 2004 , vol. 47, # 12 p. 3089 - 3104
2-[(2-ethoxyphenoxy)methyl]oxirane structure

2-[(2-ethoxyphe...

CAS#:5296-35-5

Ethanolamine-O-sulfate structure

Ethanolamine-O-...

CAS#:926-39-6

~39%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Supernus Pharmaceuticals Inc. Patent: US2011/251198 A1, 2011 ; Location in patent: Page/Page column 13-14 ;
N/A structure

N/A

CAS#:1338700-16-5

~%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Supernus Pharmaceuticals Inc. Patent: US2011/251198 A1, 2011 ;
2-[(2-ethoxyphenoxy)methyl]oxirane structure

2-[(2-ethoxyphe...

CAS#:5296-35-5

~%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Supernus Pharmaceuticals Inc. Patent: US2011/251198 A1, 2011 ;
tert-butyl 2-((2-ethoxyphenoxy)methyl)morpholine-4-carboxylate structure

tert-butyl 2-((...

CAS#:1330189-29-1

~%

2-[(2-ethoxyphenoxy)methyl]morpholine Structure

2-[(2-ethoxyphe...

CAS#:46817-91-8

Literature: Letavic, Michael A.; Keith, John M.; Ly, Kiev S.; Bonaventure, Pascal; Feinstein, Mark A.; Lord, Brian; Miller, Kirsten L.; Motley, S. Timothy; Nepomuceno, Diane; Sutton, Steven W.; Carruthers, Nicholas I. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 21 p. 5796 - 5799

 Synonyms

Emovit
Morpholine,2-((2-ethoxyphenoxy)methyl)
Viloxazinum [INN-Latin]
2-(2-Ethoxy-phenoxymethyl)-morpholine
2-(o-ethoxyphenoxymethyl)morpholine
viloxazine
Viloxazina [INN-Spanish]
Viloxazin
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