Natrium-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methansulfonat

Bezeichnung:Natrium-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methansulfonat

CAS-Nr68-89-3

Englisch Name:Metamizole sodium

CBNumberCB7741339

SummenformelC13H16N3NaO4S

Molgewicht333.34

MOL-Datei68-89-3.mol

Synonyma

Natrium-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methansulfonat

Natrium-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methansulfonat physikalisch-chemischer Eigenschaften

Schmelzpunkt	227 °C
Dichte	1.388 g/cm3
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand	Solid
Farbe	Minute crystals
Stabilität	Stable. Incompatible with strong oxidizing agents.
InChI	InChI=1S/C13H17N3O4S.Na/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11;/h4-8H,9H2,1-3H3,(H,18,19,20);/q;+1/p-1
InChIKey	DJGAAPFSPWAYTJ-UHFFFAOYSA-M
SMILES	[Na+].C(N(C1=C(C)N(C)N(C2=CC=CC=C2)C1=O)C)S([O-])(=O)=O
CAS Datenbank	68-89-3(CAS DataBase Reference)
NIST chemische Informationen	Dipyrone(68-89-3)
EPA chemische Informationen	Methanesulfonic acid, 1-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]-, sodium salt (1:1) (68-89-3)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	42/43
S-Sätze:	36
WGK Germany	2
RTECS-Nr.	PB1300000
HS Code	29331920
Toxizität	LD50 orl-rat: 3 g/kg ARZNAD 21,719,71

Gefahreninformationscode (GHS)

Metamizole sodium Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
solid
Verwenden
A non-steroidal anti-inflammatory drug that, when coadministered with morphine, potentiates its antinociceptive action and delays the development of tolerance. Dipyrone is a relatively selective inhibitor of cyclooxygenase-3 (COX-3), with lower activity against COX-1 and no activity against COX-2. Blocks PGE2-induced hyperalgesia in several models.
Verwenden
Methamizole sodium has expressed analgesic and fever-reducing properties and poorly expressed anti-inflammatory action, and is very convenient in cases where high concentrations of drug need to be quickly reached. Methamizole sodium is used for relieving pain of various origins (renal and biliary colic, neuralgia, myalgia, trauma, burns, headaches, and toothaches). Use of this drug may cause allergic reactions, and long-term use may cause granulocytopenia.
Verwenden
Dipyrone is a non-steroidal anti-inflammatory drug that, when coadministered with morphine, potentiates its antinociceptive action and delays the development of tolerance. Dipyrone is a relatively sel ective inhibitor of cyclooxygenase-3 (COX-3), with lower activity against COX-1 and no activity against COX-2. Dipyrone blocks PGE2-induced hyperalgesia in several models.
Definition
ChEBI: An organic sodium salt of antipyrine substituted at C-4 by a methyl(sulfonatomethyl)amino group, commonly used as a powerful analgesic and antipyretic.
Trademarks
Diprofarn (Farmitalia, Societa Farmaceutici Italia, Italy); Novaldin (Sterling Winthrop);Abalgine;Acabel compositum;Acefalgin;Acrobal;Acrogesico;Adolkin;Algia-nil;Alginodia compose;Algisedal;Algobuscopan;Algopriv;Algopyriv;Alkozin;Amiglan;Aminocid;Amitralil;Ampi tumisan;Anadex;Analcedor;Analject;Anarinyl;Anchrina;Anespas cpto;Angiter;Ankaljin;An-t;Apasmo;Arantil;Arquidon;Artritex;Ascorbalgine;Ascortin;Aseptobron;Atecilina;Atn-020/2;Avafortan;Ayoral;Bayer 1387;Bebealjin;Bebigut;Belatropin;Belflex/2;Beneurin;Bexopirona;Biogamma2;Biotangin;Bipasmin compuesto;Bort;Bristacilia;Britercina;Bromalgin;Bromalgon;Broncofenil;Broncolysin;Bucarboxal;Buscapina comp.;Buscapina compuesto;Buscapina compuestum;Buscol compositum;Buscopan composto;Buscopan compostum;Buscopina compostum;Butalgine;Butylpan;Calgayan-c;Calmetron;Camizol;Causalon;Cessantyl;Chini-med;Cintaverin compuesto;Clizim;Clofexan;Codalgin;Codasal injetavel;Colgenol;Comaril 5000;Corilin pediatric;Cortempirol;Cortitracin;Cronopen balsamico;Deltricin;Devalgin;Dexa butarin;Di-bal-rone;Dimethedon;Dinopirina;Dioxadol;Dipirona;Diprofarm;Dipyrivo;Dispalgine;Divarin;Divarmin;Do-ba-rone;Dolatets;Dolazon;Dolemicin;Dolispasmo;Dolo adamon;Dolo baralgine;Dolo buscopan;Dolo nerv;Dolo neurobion forte;Dolo pangavit;Dolo raptalgin;Dolo spasuret;Dolojudolor;Dolo-neurobion;Dolopirina;Doloscopin;Dopiral;Dorflex merrell;Dorlisin;Doron;Dorscopena;D-pron;Dumalgin;Duralnordin;Dya-tran;Edgartet;Eespanal;Enzipan combinado;Espasfher;Espasmir;Espasmo-cibalgina;Espasmoqual;Espasmotex;Espasmoviral;Espyre;Farbinol;Flogolisin;G.r. ulix compuesto;Genservet;Gentil;Geralgine;Glutisal;Greplicina belsa;H 116;H 117;H 118;Hagalgin;Hasain;Indextron;Influbene;Kb-502;Kefren;Kesan;Killgrip;Kipyrone;Kitax alpha;Kitax n;Konitan;Labymetacincpo;Lactmicina;Lagalgine;Lamprcsnum;Lapalgine;Larq 731;Lasain;Lavaciclina;Levapa;Levismon;Lisalgil;Magdor;Magnalsa;Magnemidon;Mapir;Mecoten;Megal;Melpen;Menalgine;Mialgan;Minalgine;Minoval;Miocitalgan;Nadalgine;Naftalgin;Naltrium;Napasone;Nartate;Natralgin;Natric;Neo-melubrim;Neo-melubrina;Neo-melubrine;Neo-oxipen;Neosal-n;Neosoldina;Neuro-fortamin;Nisidina;Nlo conicilina balsamica;Nobelgin;Nolotil composirum;Notermin;Novacid;Novalcina;Novalgetol;Novalgin quinine;Novalgina;Novalgine;Nova-lyseen;Novamidazofen;Novamidazophen;Novamideazophene;Novaminophenazone;Novaminsulfon ratiopharm;Novaminsulfone sodium;Novaminsulfonium;Novaminsulfonum;Novaminsulton;Novazolon dexametasona;Noveltex;Novemida;Novemina;Novil;Oftlamin;Orphalginen;Ortopirona;Oxiquiunazine;Pabron gold;Panalvon;Patalgin;Pentrodin;Phanalgin;Pharmalgine;Porbiot;Pplan 2500;Probaphen;Prodol;Prydonnal;Pydirone;Pyralgine;Pyrilgin;Pyriligin;Pyrisan;Quarelin;Reflex rectal;Relexal compuesto;Repriman;Resquim;Rheuma-spalt;Ridol;Rumalisine;Rupalgin;Santeprednisan a;Sebon;Sedabel;Sedarel;Sedarene;Sedazepane;Selpiran;Sertalanalgesico;Severen;Sinalgex;Sintaverin;Sinvirol;Spasdolsom;Spaslar;Spasmalgon;Spasmium-comp.;Spasmizol;Spasmodor;Spasmopyralgin;Spasmothil;Sufonovin;Sulfonovin;Supadol;Supergine;Surpyrine;Tanper;Tapal;Tega-pyrone;Tempil;Tepal;Termonil;Tetrabal-hosbon;Tetraspasmil;Tiadexol;Tiartan;Toloxin andromaco;Trenteron;Triartan;Trinalgen.
Weltgesundheitsorganisation (WHO)
Metamizole sodium, a pyrazolone derivative with analgesic, antipyretic and antinflammatory activity, was introduced in 1921 and has since been widely available in over-the-counter products. By the early 1970s its use had been associated, as with some other pyrazolones, with serious and sometimes fatal adverse reactions, notably cases of blood dyscrasias including agranulocytosis, which led to its withdrawal by some regulatory authorities. Although preparations of metamirole sodium are prohibited in certain countries, they remain widely available in others and, in some cases, in over-the-counter products.
Sicherheitsprofil
Poison by subcutaneous route. Moderately toxic by several other routes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. Questionable carcinogen with experimental neoplastigenic data. See also SULFONATES. When heated to decomposition it emits very toxic fumes of NOx,, Na2O, and SOx,.
Synthese
Methamizole sodium, 1-phenyl-2,3-dimethyl-4-methylaminopyrazolone-5-N-sodium methansulfonate (3.2.16), is synthesized in a multi-stage synthesis from acetoacetic ester and phenylhydrazine. Their reaction leads to the formation of 1-phenyl- 3-methylpyrazolone-5 (3.2.9). Methylation of this product with methyl iodide gives 1-phenyl- 2,3-dimethylpyrazolone-5 (3.2.10). This compound is used independently in medicine as a fever-reducing and anti-inflammatory analgesic under the name antipyrin. It undergoes nitrozation by sodium nitrite in an acidic medium, forming 1-phenyl-2,3-dimethyl-4- nitrozopyrazolone-5 (3.2.11). Reduction of the nitrous derivative (3.2.11) by different reducing agents leads to the formation of 1-phenyl-2,3-dimethyl-4-aminopyrazolone-5 (3.2.12). This product is reacted with benzaldehyde, forming an easily separable crystalline 1-phenyl- 2,3-dimethyl-4-benzylidenaminopyrazolone-5 (3.2.13), which is methylated at the imine atom of nitrogen by dimethylsulfate, giving a quaternary salt (3.2.14). Hydrolysis of the resulting salt gives 1-phenyl-2,3-dimethyl-4-methylaminopyrazolone-5 (3.2.15). Treating the product with a water solution of a mixture of sodium bisulfite and formaldehyde leads to the formation of 1-phenyl-2,3-dimethyl-4-methylaminopyrazolone-5-N-sodium methanesulfonate (3.2.16), the desired sodium methamizole [72¨C75].

Metamizole sodium Upstream-Materialien And Downstream Produkte

Natrium-[(2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino]methansulfonat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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