Compound: viloxazine
SMILES: O1C(CNCC1)COc2c(OCC)cccc2
InChIKey: YWPHCCPCQOJSGZ-UHFFFAOYSA-N
Synonyms: viloxazine, 46817-91-8, 2-((2-ETHOXYPHENOXY)METHYL)MORPHOLINE, Viloxazin, 2-[(2-ethoxyphenoxy)methyl]morpholine, Viloxazina, Viloxazinum, Morpholine, 2-((2-ethoxyphenoxy)methyl)-, 5I5Y2789ZF, Morpholine, 2-[(2-ethoxyphenoxy)methyl]-, DTXSID6057900, RefChem:56627, DTXCID0031683, N06AX09, ICI58,834, 256-281-7, Emovit, 2-(2-Ethoxyphenoxymethyl)tetrahydro-1,4-oxazine, CHEMBL306700, Viloxazine (INN), VILOXAZINE [INN], Viloxazine [INN:BAN], Viloxazinum [INN-Latin], Viloxazina [INN-Spanish], CCRIS 9180, EINECS 256-281-7, UNII-5I5Y2789ZF, 2-(o-ethoxyphenoxymethyl)morpholine, MFCD00865384, ICI-58,834, VILOXAZINE [MI], VILOXAZINE [VANDF], VILOXAZINE [WHO-DD], Oprea1_394269, SCHEMBL34168, DivK1c_001019, orb1689691, SCHEMBL29359040, CHEBI:94405, GTPL11502, KBio1_001019, NINDS_001019, BDBM50025691, EBC-06656, 2-[(o-Ethoxyphenoxy)methyl]morpholine, AKOS013400287, 2-(2-Ethoxy-phenoxymethyl)-morpholine, DB09185, HY-W380450, IDI1_001019, TS-09233, DB-363818, CS-0491105, NS00007820, D08673, EN300-253642, H36386, 2-(2-Ethoxy-phenoxymethyl)-morpholine(viloxazine), Q907148, (+/-)-2-(O-ETHOXYPHENOXYMETHYL)MORPHOLINE, 2-(2-Ethoxy-phenoxymethyl)-morpholine (viloxazine), BRD-A59198242-003-01-1, BRD-A59198242-003-02-9, Z1235945951
Theoretical properties:
molecular_formula: C13H19NO3
molecular_weight: 237.29 g/mol
exact_mass: 237.13649347 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 17
topological_polar_surface_area: 39.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 178-180
Descriptions:
pubchem: 2-[(2-ethoxyphenoxy)methyl]morpholine is an aromatic ether.
chembl: VILOXAZINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Viloxazine, sold under the brand name Qelbree among others, is a selective norepinephrine reuptake inhibitor medication that is indicated in the treatment of attention deficit hyperactivity disorder (ADHD) in children and adults. It was marketed for almost 30 years as an antidepressant for the treatment of depression before being discontinued and subsequently repurposed as a treatment for ADHD. Viloxazine is taken orally. It was used as an antidepressant in an immediate-release form and is used in ADHD in an extended-release form, although current evidence indicates that it is significantly less effective at reducing ADHD symptoms compared to stimulant medications like methylphenidate.
Side effects of viloxazine include insomnia, headache, somnolence, fatigue, nausea, vomiting, decreased appetite, dry mouth, constipation, irritability, increased heart rate, and increased blood pressure. Rarely, the medication may cause suicidal thoughts and behaviors. It can also activate mania or hypomania in people with bipolar disorder. Viloxazine acts as a selective norepinephrine reuptake inhibitor (sNRI). The immediate-release form has an elimination half-life of 2.5 hours while the half-life of the extended-release form is 7 hours.
Viloxazine was first described by 1972 and was marketed as an antidepressant in Europe in 1974. It was not marketed in the United States at this time. The medication was discontinued in 2002 for commercial reasons. However, it was repurposed for the treatment of ADHD and was reintroduced, in the United States, in April 2021. Viloxazine is a non-stimulant medication; it has no known misuse liability and is not a controlled substance.