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SML3133

Sigma-Aldrich

Viloxazine hydrochloride

≥95% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C13H19NO3 · HCl
Numéro CAS:
35604-67-2
Poids moléculaire :
273.76
Numéro MDL:
MFCD00661100
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥95% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

HJOCKFVCMLCPTP-UHFFFAOYSA-N

Actions biochimiques/physiologiques

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).

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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
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)
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
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
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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