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SML3133

Sigma-Aldrich

Viloxazine hydrochloride

≥95% (HPLC)

Synonym(s):

1. 2-(2-Ethoxyphenoxymethyl-2,3,5,6-tetrahydro-1,4-oxazine hydrochloride salt, 2-((2-Ethoxyphenoxy)methyl)morpholine hydrochloride, 2-(o-Ethoxyphenoxymethyl)morpholine hydrochloride, 2-[(2-Ethoxyphenoxy)methyl]morpholinium chloride, I.C.I. 58,834 HCl, ICI 58,834 HCl, SPN-812, Viloxazine HCl, rac Viloxazine HCl, rac Viloxazine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C13H19NO3 · HCl
CAS Number:
35604-67-2
Molecular Weight:
273.76
MDL number:
MFCD00661100
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CCOC1=C(OCC2OCCNC2)C=CC=C1.Cl

InChI

1S/C13H19NO3.ClH/c1-2-15-12-5-3-4-6-13(12)17-10-11-9-14-7-8-16-11;/h3-6,11,14H,2,7-10H2,1H3;1H

InChI key

HJOCKFVCMLCPTP-UHFFFAOYSA-N

Biochem/physiol Actions

Viloxazine (ICI 58,834) is an orally active serotonin norepinephrine modulating agent (SNMA) originally reported as a norepinephrine reuptake inhibitor (NRI) with antidepressant (ED10 from 0.3-1 mg/kg p.o. against reserpine-induced hypothermia in mice), while exhibiting less sedative efficacy (locomotor activity reduction ED10 from 3-10 mg/kg p.o. in mice) and no monoamine oxidase inhibitory potency. Viloxazine shows 5-HT2B antagonist and 5-HT2C agonist activity in vitro and increases extracellular 5-HT levels in the prefrontal cortex (PFC) in vivo, a brain area implicated in Attention deficit hyperactivity disorder (ADHD).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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2-(2-ethoxyphenoxymethyl)tetrahydro-1,4-oxazine hydrochloride, a potential psychotropic agent.
K B Mallion et al.
Nature, 238(5360), 157-158 (1972-07-21)
R Howe et al.
Journal of medicinal chemistry, 19(8), 1074-1074 (1976-08-01)
The optical isomers of 2-(2-ethoxyphenoxymethyl)tetrahydro-1,4-oxazine (viloxazine) and 2-(3-methoxyphenoxymethyl)tetrahydro-1,4-oxazine have been prepared and absolute configurations have been assigned. In their action on the central nervous system the S isomers are at least ten times more potent than the R isomers. The
W Lippman et al.
Canadian journal of physiology and pharmacology, 54(4), 494-509 (1976-08-01)
The effects of viloxazine, a clinically effective antidepressant, on noradrenaline (NA) and 5-hydroxytryptamine (5-HT) uptake and various related pharmacological activities were determined and compared to those of the tricyclic antidepressants desimipramine, imipramine, and amitriptyline. Viloxazine inhibitied [3H]NA uptake in the
D T Greenwood et al.
Journal of medicinal chemistry, 18(6), 573-577 (1975-06-01)
Some 2-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazines have been shown to possess marked antidepressant activity. The 1,4-oxazines were synthesized by lithium aluminum hydride reduction of the readily available 6-aryloxymethyl-2,3,5,6-tetrahydro-1,4-oxazin-3-ones. High antidepressant activity was associated with ortho substitution of the 2-phenoxymethyl group and with 1,4-oxazines devoid
Chungping Yu et al.
Journal of experimental pharmacology, 12, 285-300 (2020-09-19)
Viloxazine was historically described as a norepinephrine reuptake inhibitor (NRI). Since NRIs have previously demonstrated efficacy in attention deficit/hyperactivity disorder (ADHD), viloxazine underwent contemporary investigation in the treatment of ADHD. Its clinical and safety profile, however, was found to be

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