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5-Methoxy-1-(4-(trifluoromethyl)phenyl)-1-pentanone O-(2-aminoethyl)oxime

HCID 3404
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
54739-18-3
Standard SMILES
COCCCCC(=NOCCN)c1ccc(C(F)(F)F)cc1
InChIKey
CJOFXWAVKWHTFT-UHFFFAOYSA-N
Molecular formula
C15H21F3N2O2
Average molar mass
318.33 g/mol
Monoisotopic mass
318.1555124

Names & identifiers

Preferred name
5-Methoxy-1-(4-(trifluoromethyl)phenyl)-1-pentanone O-(2-aminoethyl)oxime
IUPAC
2-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine
English name
Fluvoxamine
Molecular formula
C15H21F3N2O2
Molecular weight
318.33

Names & synonyms

61718-81-8RefChem:10730545-Methoxy-1-(4-(trifluoromethyl)phenyl)-1-pentanone O-(2-aminoethyl)oxime2-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]pentylidene]amino]oxyethanamine917096-37-8(Z)-FluvoxamineLuvox (Salt/Mix)Dumirox (Salt/Mix)Faverin (Salt/Mix)Fevarin (Salt/Mix)Maveral (Salt/Mix)Floxyfral (Salt/Mix)
Show more names
2-[[5-methoxy-1-[4-(trifluoromethyl)phenyl]-pentylidene]amino]oxyethanamineFLUVOXAMINEFluvoxamine USP/EP/BPFluvoxamine Impurity 7Fluvoxamine in MethanolFluvoxamine See: F603500Fluvoxamine Also See: F603500δ-Methoxy-4'-(trifluoromethyl)valerophenone (E)-O-(2-aminoethyl)oxime(E)-ω-Methoxy-4'-(trifluoromethyl)valerophenone O-(2-aminoethyl)oxime5-Methoxy-4’-(triflluoromethyl)valerophenone(E)-O-(2-aminoethyl) oxime
Fluvoxaminum [INN-Latin]Fluvoxamina [INN-Spanish]MK-264 (Salt/Mix)DU-23000 (Salt/Mix)fluvoxamine-CRNCGC00018193-06Fluvoxamine impurity B(Z)-Fluvoxamine - EP

Properties

Computed structural propertiesFilling in

XLogP
2.6
Topological polar surface area
56.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
9
Heavy atoms
22
Formal charge
0
Complexity
327

Physicochemical properties

Melting point
122 °C · 122 °C
Boiling point
370.6 · 370.6±52.0 °C(Predicted)
Density
1.16 · 1.16±0.1 g/cm3(Predicted)
storage temp.
2 · Sealed in dry,2-8°C
solubility
Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
pka
8.7 · pKa 8.7 (Uncertain)
form
powder to crystal
color
White to Almost white
InChI
InChI=1S/C15H21F3N2O2/c1-21-10-3-2-4-14(20-22-11-9-19)12-5-7-13(8-6-12)15(16,17)18/h5-8H,2-4,9-11,19H2,1H3/b20-14+
InChIKey
CJOFXWAVKWHTFT-XSFVSMFZSA-N
SMILES
C(=N/OCCN)(\C1=CC=C(C(F)(F)F)C=C1)/CCCCOC
CAS DataBase Reference
54739 · 54739-18-3(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
fluvoxamine
FDA UNII
4 L1XPO44W · O4L1XPO44W

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Signal word
Danger
Symbol(GHS)
GHS07,GHS09,GHS06
Hazard statements
H302-H335-H331-H410-H319
REACH Registrations
Active
Precautionary statements
P273-P391-P501-P264-P280-P305+P351+P338-P337+P313P-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 3 items

HistoryThe development of Fluvoxamine began in the 1970s, led by a research team at the Belgian pharmaceutical company Solvay. As the first successfully commercialized selective serotonin reuptake inhibitor (SSRI), fluvoxamine was designed and synthesized to exert its antidepressant effect by highly selectively inhibiting the presynaptic serotonin transporter, while exhibiting a higher safety profile compared to tricyclic antidepressants. This compound received its first clinical approval and market launch in Switzerland in 1983, marking the beginning of the SSRI era. Leading researchers in psychopharmacology, including C. M. van Hout, systematically elucidated the pharmacological properties and clinical efficacy of fluvoxamine. With the expansion of its clinical applications, fluvoxamine has also established a therapeutic role in indications such as obsessive-compulsive disorder, and during the COVID-19 pandemic, its re-evaluation as a potential immunomodulator sparked renewed research interest, reflecting its evolution from a classic antidepressant to a multi-purpose psychopharmacological drug.

UsesA selective serotonin reuptake inhibitor (SSRI) used as an anti-depressant.

General DescriptionThe E-isomer of fluvoxamine (Luvox) can fold after protonation to the β-arylamine–like grouping. Here,the “extra” hydrophobic group is aliphatic.

Upstream & downstream products

Upstream raw materials

2-Aminooxyethylamine dihydrochloride5-Methoxy-1-[4-(trifluoromethyl)phenyl]-1-pentanoneMaleic anhydride

Suppliers89 total

北京华美互利生物化工010-56205725 · [email protected]

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
54739-18-3、61718-81-8
PubChem CID
3404
DTXSID
DTXSID70860673
ATC code
6 AB08 · N06AB08
NIST Chemistry Reference
Fluvoxamine(54739-18-3)
Symbol(GHS)
7 · GHS07,GHS09,GHS06
Signal word
Danger
Hazard statements
302 · H302-H335-H331-H410-H319
Precautionary statements
273 · P273-P391-P501-P264-P280-P305+P351+P338-P337+P313P-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P264-P270-P301+P312-P330-P501
REACH Registrations
Active
上海阿拉丁生化科技股份有限公司
400-6206333 13167063860 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
湖北长耀生物科技有限公司17683887209 17683887209 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
杭州明苏科技有限公司571-88199336 17826832916 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
湖北成海化工有限公司027-59220433 18327245847 · [email protected]
ZHEJIANG JIUZHOU CHEM CO., LTD+86-0576225566889 +86-13454675544 · [email protected];[email protected];[email protected]
杭州云易国科生物科技有限公司18457506494 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
上海遐瑞医药科技有限公司+86 21 61551611
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
武汉锦烁达新材料有限公司19292735370 19292735370 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
北京奥秘佳得医药科技有限公司+86-13522808617 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
上海楼岚生物科技有限公司021-52996696,15000506266 15000506266
海南瀚海致远生物科技有限公司18171012772 · [email protected]
杭州安凯生物医药有限公司+86-0571-28186870; +undefined8613073685410 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
淄博航宇生物科技发展有限公司13053322091 13053322091 · [email protected]
深圳卓越生物医药科技有限公司26050679 18318671572 · [email protected]
上海烁点生物科技有限公司18221553137 · [email protected]
江西普欣生物科技有限公司15867635987 · [email protected]
风咏生物(AbMole)021-10000000 13000000000 · [email protected]
台州市瑞欣化工有限公司0576-89085261 15867635987 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
河南中梵实业发展有限公司+86-18906033525 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Musechem+1-800-259-7612 · [email protected]
江苏艾康生物医药研发有限公司025-58859352 19370895928 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Fluvoxamine is an oxime O-ether that is benzene substituted by a (1E)-N-(2-aminoethoxy)-5-methoxypentanimidoyl group at position 1 and a trifluoromethyl group at position 4. It is a selective serotonin reuptake inhibitor that is used for the treatment of obsessive-compulsive disorder. It has a role as an antidepressant, a serotonin uptake inhibitor and an anxiolytic drug. It is a 5-methoxyvalerophenone O-(2-aminoethyl)oxime and a member of (trifluoromethyl)benzenes. It is functionally related to a (trifluoromethyl)benzene.