Product Name

  • Name

    Dipyrone

  • EINECS 200-694-7
  • CAS No. 68-89-3
  • Density 1.388 g/cm3
  • Solubility easily soluble in water, little soluble in alcohol
  • Melting Point 187oC
  • Formula C13H16N3NaO4S
  • Boiling Point
  • Molecular Weight 333.344
  • Flash Point
  • Transport Information
  • Appearance solid
  • Safety 36
  • Risk Codes 42/43
  • Molecular Structure Molecular Structure of 68-89-3 (Dipyrone)
  • Hazard Symbols HarmfulXn
  • Synonyms Dipyrone(6CI);Methanesulfonic acid, (antipyrinylmethylamino)-, sodium salt (8CI);ARPF;Optalgin;Pyralgine;Pyretin;Sodium1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethanesulfonate;Sodium noramidopyrine methanesulfonate;Sulpin;Sulpyrine;Algopyrin;Anador;Analgin;Andolor;Conmel;Diprofarn;Metamizol;Metamizole sodium;Metamizole sodium salt;Methamizole sodium;Metilon;Neo-melubrine;Noramidopyrine methanesulfonatesodium;Noraminophenazone sodium mesylate;Novalgetol;Novamidazophen;Novaminsulfone;Novaminsulfonium;Noveltex;
  • PSA 95.75000
  • LogP 1.50410

Synthetic route

metamizol
68-89-3

metamizol

Metamizol
50567-35-6

Metamizol

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20 - 30℃; for 1h; Solvent; Reagent/catalyst;93.3%
metamizol
68-89-3

metamizol

4-methylaminoantipyrine
519-98-2

4-methylaminoantipyrine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 60℃; for 3h;86.7%
In water for 4h; Irradiation; Yield given;
bromopentacarbonylmanganese(I)
14516-54-2

bromopentacarbonylmanganese(I)

metamizol
68-89-3

metamizol

fac-[Mn(CO)3(metamizole)]

fac-[Mn(CO)3(metamizole)]

Conditions
ConditionsYield
With acetone for 0.333333h; Inert atmosphere; Darkness; Reflux;82%
metamizol
68-89-3

metamizol

Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid
38988-02-2

Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid

Conditions
ConditionsYield
With dihydrogen peroxide for 0.0833333h;79%
metamizol
68-89-3

metamizol

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

(1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethane sulphonate)nickel(II)
84110-66-7

(1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethane sulphonate)nickel(II)

Conditions
ConditionsYield
In ethanol for 1 - 3h; Reflux;77%
cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

metamizol
68-89-3

metamizol

(1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethane sulphonate)cobalt(II)
84110-65-6

(1-phenyl-2,3-dimethyl-5-pyrazolone-4-methylaminomethane sulphonate)cobalt(II)

Conditions
ConditionsYield
In ethanol for 1 - 3h; Reflux;73%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

metamizol
68-89-3

metamizol

Cu([(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonate)2

Cu([(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonate)2

Conditions
ConditionsYield
In ethanol for 1 - 3h; Reflux;68%
diammonium hexachlororhenate(IV)

diammonium hexachlororhenate(IV)

metamizol
68-89-3

metamizol

2C13H17N3O4S*2H(1+)*{ReCl6}(2-)=(C13H18N3O4S)2{ReCl6}

2C13H17N3O4S*2H(1+)*{ReCl6}(2-)=(C13H18N3O4S)2{ReCl6}

Conditions
ConditionsYield
In hydrogenchloride satg. 6 M HCl with (NH4)2(ReCl6); treating soln. with ethanol satd. with NaC13H16N3O4S (25°C, magnetic stirring);; pptn.; rinsing with 6 M HCl; drying to const. wt. at 105°C; elem. anal. (Re is partially oxidized);;50%
tetracyanodinitrosylmanganate(0)
125841-54-5

tetracyanodinitrosylmanganate(0)

metamizol
68-89-3

metamizol

Mn(2+)*2NO*2CN(1-)*2Na(1+)*2C13H16N3O4S(1-)*H2O = [Mn(NO)2(CN)2Na2(C13H16N3O4S)2]*H2O

Mn(2+)*2NO*2CN(1-)*2Na(1+)*2C13H16N3O4S(1-)*H2O = [Mn(NO)2(CN)2Na2(C13H16N3O4S)2]*H2O

Conditions
ConditionsYield
In acetic acid aq. acetic acid; refluxing (80°C, 2 h); ppt. washing (dild. acetic acid, water), drying (vac.); elem. anal.;40%
potassium hexabromorhenate (IV)

potassium hexabromorhenate (IV)

metamizol
68-89-3

metamizol

2C13H17N3O4S*2H(1+)*{ReBr6}(2-)=(C13H18N3O4S)2{ReBr6}

2C13H17N3O4S*2H(1+)*{ReBr6}(2-)=(C13H18N3O4S)2{ReBr6}

Conditions
ConditionsYield
In hydrogen bromide aq. HBr; satg. 6 M HBr with K2(ReBr6); treating soln. with ethanol satd. with NaC13H16N3O4S (25°C, magnetic stirring);; pptn.; rinsing with 6 M HBr; drying to const. wt. at 105°C; elem. anal. (Re is partially oxidized);;35%
metamizol
68-89-3

metamizol

1-phenyl-3,4-dimethyl-5-hydroxy-imidazoline-2-on
96337-48-3

1-phenyl-3,4-dimethyl-5-hydroxy-imidazoline-2-on

Conditions
ConditionsYield
In water at 20℃; for 1.5h; Product distribution; Irradiation; photochemical decomposition studies to different products at different times;32%
In water at 20℃; for 1.5h; Irradiation;32%
metamizol
68-89-3

metamizol

A

3-Methyl-1-phenyl-2-pyrazoline-4,5-dione
881-05-0

3-Methyl-1-phenyl-2-pyrazoline-4,5-dione

B

1-acetyl-1-methyl-2-phenylhydrazine
38604-70-5

1-acetyl-1-methyl-2-phenylhydrazine

C

Sodium; [methyl-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-amino]-methanesulfonate

Sodium; [methyl-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-amino]-methanesulfonate

D

Glyoxilic acid
298-12-4

Glyoxilic acid

E

4-hydroxyantipyrine
1672-63-5

4-hydroxyantipyrine

F

5-hydroxy-1,5-dimethyl-3-phenyl-imidazolidine-2,4-dione
50871-97-1

5-hydroxy-1,5-dimethyl-3-phenyl-imidazolidine-2,4-dione

Conditions
ConditionsYield
In water Kinetics; Irradiation; photochemical decomposition, λ=254 nm;
metamizol
68-89-3

metamizol

A

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one
83-07-8

4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one

B

4-methylaminoantipyrine
519-98-2

4-methylaminoantipyrine

Conditions
ConditionsYield
In water Kinetics; Irradiation; photochemical decomposition, λ=254 nm;
metamizol
68-89-3

metamizol

A

formaldehyd
50-00-0

formaldehyd

B

4-methylaminoantipyrine
519-98-2

4-methylaminoantipyrine

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 0.5h;
metamizol
68-89-3

metamizol

A

phenyl isocyanate
1197040-29-1

phenyl isocyanate

B

1,5-dimethyl-3-phenyl-2,4-imidazolidinedione
2221-10-5

1,5-dimethyl-3-phenyl-2,4-imidazolidinedione

C

Sodium; [(2,3-dihydroxy-1,3-dimethyl-aziridin-2-yl)-methyl-amino]-methanesulfonate

Sodium; [(2,3-dihydroxy-1,3-dimethyl-aziridin-2-yl)-methyl-amino]-methanesulfonate

D

Sodium; [methyl-(2-{1-[(E)-methylimino]-ethyl}-3-oxo-1-phenyl-aziridin-2-yl)-amino]-methanesulfonate

Sodium; [methyl-(2-{1-[(E)-methylimino]-ethyl}-3-oxo-1-phenyl-aziridin-2-yl)-amino]-methanesulfonate

E

Sodium; [(4-hydroxy-1,5-dimethyl-3-oxo-2-phenyl-pyrazolidin-4-yl)-methyl-amino]-methanesulfonate

Sodium; [(4-hydroxy-1,5-dimethyl-3-oxo-2-phenyl-pyrazolidin-4-yl)-methyl-amino]-methanesulfonate

F

Formanilid
103-70-8

Formanilid

Conditions
ConditionsYield
In water Kinetics; Irradiation; photochemical decomposition, λ=254 nm;
metamizol
68-89-3

metamizol

A

phenyl isocyanate
1197040-29-1

phenyl isocyanate

B

Sodium; [(2,3-dihydroxy-1,3-dimethyl-aziridin-2-yl)-methyl-amino]-methanesulfonate

Sodium; [(2,3-dihydroxy-1,3-dimethyl-aziridin-2-yl)-methyl-amino]-methanesulfonate

C

Sodium; [methyl-(2-{1-[(E)-methylimino]-ethyl}-3-oxo-1-phenyl-aziridin-2-yl)-amino]-methanesulfonate

Sodium; [methyl-(2-{1-[(E)-methylimino]-ethyl}-3-oxo-1-phenyl-aziridin-2-yl)-amino]-methanesulfonate

D

Sodium; [(4-hydroxy-1,5-dimethyl-3-oxo-2-phenyl-pyrazolidin-4-yl)-methyl-amino]-methanesulfonate

Sodium; [(4-hydroxy-1,5-dimethyl-3-oxo-2-phenyl-pyrazolidin-4-yl)-methyl-amino]-methanesulfonate

E

1-phenyl-3,4-dimethylimidazol-2(1H)-one
16939-00-7

1-phenyl-3,4-dimethylimidazol-2(1H)-one

F

Formanilid
103-70-8

Formanilid

Conditions
ConditionsYield
In water Kinetics; Irradiation; photochemical decomposition, λ=254 nm;
metamizol
68-89-3

metamizol

1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(N,N'-dimethyl-N,N'-methanediyl-diamino)-bis-pyrazol-3-one
810-16-2

1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(N,N'-dimethyl-N,N'-methanediyl-diamino)-bis-pyrazol-3-one

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;
metamizol
68-89-3

metamizol

A

1-acetyl-1-methyl-2-phenylhydrazine
38604-70-5

1-acetyl-1-methyl-2-phenylhydrazine

B

Methylaminooxoessigsaeure-2-acetyl-2-methyl-1-phenylhydrazid
92569-10-3

Methylaminooxoessigsaeure-2-acetyl-2-methyl-1-phenylhydrazid

C

Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid
38988-02-2

Oxalsaeure-mono(2-acetyl-2-methyl-1-phenyl)hydrazid

Conditions
ConditionsYield
With sodium hydroxide; phosphate buffer; dihydrogen peroxide In water for 24h; Product distribution; Ambient temperature; var. of pH;
hydrogenchloride
7647-01-0

hydrogenchloride

water
7732-18-5

water

metamizol
68-89-3

metamizol

A

4-methylaminoantipyrine
519-98-2

4-methylaminoantipyrine

B

aminopyrine
58-15-1

aminopyrine

hydrogenchloride
7647-01-0

hydrogenchloride

water
7732-18-5

water

metamizol
68-89-3

metamizol

A

4-methylaminoantipyrine
519-98-2

4-methylaminoantipyrine

B

1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(N,N'-dimethyl-N,N'-methanediyl-diamino)-bis-pyrazol-3-one
810-16-2

1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(N,N'-dimethyl-N,N'-methanediyl-diamino)-bis-pyrazol-3-one

metamizol
68-89-3

metamizol

A

formaldehyd
50-00-0

formaldehyd

B

4-methylaminoantipyrine
519-98-2

4-methylaminoantipyrine

C

NaHSO3

NaHSO3

Conditions
ConditionsYield
With sodium hydroxide at 100℃; for 0.5h; Mechanism; dependence from temperature;
(±)-3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol
515114-52-0

(±)-3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol

metamizol
68-89-3

metamizol

3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol ((1,5-dimethyl-3-oxo-2-phenylpyrazolidin-4-yl)(methyl)amino)methanesulfonate

3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol ((1,5-dimethyl-3-oxo-2-phenylpyrazolidin-4-yl)(methyl)amino)methanesulfonate

Conditions
ConditionsYield
In acetone at 20 - 40℃;
metamizol
68-89-3

metamizol

1-phenyl-2,3-dimethyl-4-methylaminopyrazoline-5-one N-methylsulfonate magnesium hexahydrate

1-phenyl-2,3-dimethyl-4-methylaminopyrazoline-5-one N-methylsulfonate magnesium hexahydrate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / ethanol / 1 h / 20 - 30 °C
2: magnesium oxide / isopropyl alcohol / 3 h / 20 - 30 °C
View Scheme

Dipyrone Chemical Properties

IUPAC Name: Sodium [(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-methylamino]methanesulfonate
Synonyms of Aminopyrine sodium sulfonate (CAS NO.68-89-3): Dipyrone ; Methanesulfonic acid, ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino)-, sodium salt ; Methanesulfonic acid, (antipyrinylmethylamino)-, monosodium salt ; Sodium ((2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)methylamino)methanesulphonate
CAS NO: 68-89-3
Classification Code: Analgesics ; Analgesics, Non-Narcotic ; Anti-Inflammatory Agents ; Anti-inflammatory agents, non-steroidal ; Antirheumatic Agents ; Drug / Therapeutic Agent ; Human Data ; Mutation data ; Peripheral Nervous System Agents ; Reproductive Effect ; Sensory System Agents ; Tumor data
Molecular Formula: C13H16N3NaO4S
Molecular Weight: 333.3386
Molecular Structure:

Polar Surface Area: 89.54 Å2
Product Categories: PHARMACEUTICALS ; DIO - DIZForensic and Veterinary Standards ; Alphabetic ; D ; Drugs&Metabolites ; Neat Compounds ; Cosmetic Ingredients & Chemicals

Dipyrone Uses

 Aminopyrine sodium sulfonate (CAS NO.68-89-3), with detoxification, analgesic, anti-rheumatic effect, is mainly used for cooling, also used for acute arthritis, rheumatic pain, muscle pain, headache and so on.

Dipyrone Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo subcutaneous 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
mouse LC50 inhalation 37200mg/m3 (37200mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(10), Pg. 36, 1969.
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 107, Pg. 322, 1956.
mouse LD50 intravenous 2197mg/kg (2197mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
mouse LD50 oral 2891mg/kg (2891mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.
mouse LD50 subcutaneous 69mg/kg (69mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 53, 1968.
mouse LD50 unreported 2750mg/kg (2750mg/kg)   Journal of Drug Research. Vol. 4, Pg. 89, 1972.
rabbit LD50 oral 2150mg/kg (2150mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 47, 1979.
rabbit LDLo subcutaneous 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 213, 1955.
rat LC inhalation > 900mg/m3 (900mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(12), Pg. 47, 1979.
rat LD50 intramuscular 1625mg/kg (1625mg/kg)   Russian Pharmacology and Toxicology Vol. 51, Pg. 183, 1988.
rat LD50 intraperitoneal 2470mg/kg (2470mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 11, Pg. 478, 1977.
rat LD50 intravenous 2182mg/kg (2182mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 703, 1976.
rat LD50 oral 3gm/kg (3000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
rat LD50 subcutaneous 2117mg/kg (2117mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 600, 1974.

Dipyrone Safety Profile

Hazard Codes of Aminopyrine sodium sulfonate (CAS NO.68-89-3): HarmfulXn
Risk Statements: 42/43 
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 36 
S36: Wear suitable protective clothing.
WGK Germany: 2
RTECS: PB1300000
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.

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