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60166-93-0

Basic Information
CAS No.: 60166-93-0
Name: Iopamidol
Article Data: 17
Molecular Structure:
Molecular Structure of 60166-93-0 (Iopamidol)
Formula: C17H22I3N3O8
Molecular Weight: 777.09
Synonyms: 1,3-Benzenedicarboxamide,N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-hydroxy-1-oxopropyl)amino]-2,4,6-triiodo-,(S)-;1,3-Benzenedicarboxamide,N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[[(2S)-2-hydroxy-1-oxopropyl]amino]-2,4,6-triiodo-(9CI);Gastromiro;Iopamidol 300;Iopamiro;Iopamiro 370;Iopamiron 300;Iopamiron 370;Isovue;Isovue 300;Isovue 370;Jopamiron 200;Niopam;Niopam 300;Oypalomin;Oypalomin 150;Solutrast;Solutrast 370;
EINECS: 262-093-6
Density: 2.281 g/cm3
Melting Point: >320 °C (dec)
Boiling Point: 785.3 °C at 760 mmHg
Flash Point: 428.8 °C
Solubility: 473.7g/L(25 oC)
Appearance: White Crystalline Powder
PSA: 188.45000
LogP: -0.15950
Synthetic route

S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-(acetyloxy)-1-oxo-propyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

60166-93-0

Iopamidol

Conditions
ConditionsYield
With sodium hydroxide for 0.166667h;99%
With water; sodium hydroxide at 40℃; pH=~ 11;76.4%
With water; sodium hydroxide at 40℃; pH=Ca. 11;76.4%
Stage #1: S-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-[(2-(acetyloxy)-1-oxo-propyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide With water; sodium hydroxide In ISOPROPYLAMIDE at 35℃; for 7h;
Stage #2: With hydrogenchloride In ISOPROPYLAMIDE; water pH=~ 7;
With water; sodium hydroxide at 35℃; pH=12;159 g

(S)-5-(2-amino-1-methyl-2-oxoethoxy)-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

60166-93-0

Iopamidol

Conditions
ConditionsYield
With Amberlite IRA400 In water for 32h; pH=6 - 7; Product distribution / selectivity; Smiles Rearrangement;95%
With Amberlite IRA400 In water for 32h; Smiles Aromatic Rearrangement;95%
With sodium methylate In methanol; N,N-dimethyl-formamide at 25℃; Smiles rearrangement;89%
With potassium hydroxide In methanol; water
60166-91-8

S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride

534-03-2

serinol

60166-93-0

Iopamidol

Conditions
ConditionsYield
In ISOPROPYLAMIDE at 8 - 20℃; for 10h;94%
Stage #1: S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride; serinol at 44 - 48℃; for 48 - 70h;
Stage #2: With water at 52 - 57℃; for 2 - 4h;
78%

(S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid

60166-93-0

Iopamidol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphorus pentachloride / ISOPROPYLAMIDE / 6 h / 40 °C
2: triethylamine / ISOPROPYLAMIDE / 6 h / 50 °C
3: sodium hydroxide; water / 40 °C / pH ~ 11
View Scheme
Multi-step reaction with 3 steps
1: phosphorus pentachloride / N,N-dimethyl acetamide / 6 h / 40 °C
2: triethylamine / N,N-dimethyl acetamide / 6 h / 50 °C
3: water; sodium hydroxide / 40 °C / pH Ca. 11
View Scheme
35453-19-1

2,4,6-triiodo-5-aminoisophthalic acid

60166-93-0

Iopamidol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ISOPROPYLAMIDE / 22 h / 20 - 50 °C
2: phosphorus pentachloride / ISOPROPYLAMIDE / 6 h / 40 °C
3: triethylamine / ISOPROPYLAMIDE / 6 h / 50 °C
4: sodium hydroxide; water / 40 °C / pH ~ 11
View Scheme
Multi-step reaction with 4 steps
1: N,N-dimethyl acetamide / 22 h / 20 - 50 °C
2: phosphorus pentachloride / N,N-dimethyl acetamide / 6 h / 40 °C
3: triethylamine / N,N-dimethyl acetamide / 6 h / 50 °C
4: water; sodium hydroxide / 40 °C / pH Ca. 11
View Scheme
60166-91-8

S-(-)-5-[[2-(acetyloxy)-1-oxopropyl]amino]-2,4,6-triiodo-1,3-benzenedicarboxylic acid dichloride

60166-93-0

Iopamidol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / N,N-dimethyl acetamide / 6 h / 50 °C
2: water; sodium hydroxide / 40 °C / pH Ca. 11
View Scheme

C28H28B2I3N3O6

60166-93-0

Iopamidol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl acetamide / 18 h / 30 - 35 °C / Inert atmosphere; Large scale
2: sodium hydroxide; water / N,N-dimethyl acetamide / Large scale
View Scheme

C33H34B2I3N3O9

60166-93-0

Iopamidol

Conditions
ConditionsYield
With water; sodium hydroxide In N,N-dimethyl acetamide Large scale;992 g

C27H38B2I3N3O9

60166-93-0

Iopamidol

Conditions
ConditionsYield
With water; sodium hydroxide In N,N-dimethyl acetamide Large scale;992 g

C22H32B2I3N3O8

60166-93-0

Iopamidol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl acetamide / 18 h / 20 °C / Inert atmosphere
2: water / N,N-dimethyl acetamide / 1 h
3: sodium hydroxide; water / 35 °C / pH 12
View Scheme
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Chemistry

Molecular Structure of Iopamiron (CAS NO.60166-93-0):

IUPAC Name: 1-N,3-N-bis(1,3-dihydroxypropan-2-yl)-5-[[(2S)-2-hydroxypropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarboxamide 
Empirical Formula: C17H22I3N3O8
Molecular Weight: 777.0853
H bond acceptors: 11
H bond donors: 8
Freely Rotating Bonds: 15
Polar Surface Area: 107.08Å2
Index of Refraction: 1.738
Molar Refractivity: 137.2 cm3
Molar Volume: 340.6 cm3
Surface Tension: 86.5 dyne/cm
Density: 2.281 g/cm3
Flash Point: 428.8 °C
Enthalpy of Vaporization: 119.83 kJ/mol
Boiling Point: 785.3 °C at 760 mmHg
Vapour Pressure: 5.57E-26 mmHg at 25°C
Melting point: >3200C (dec)
EINECS: 262-093-6
Product Categories: Diagnostic; Intermediates & Fine Chemicals; Pharmaceuticals
InChI
InChI=1/C17H22I3N3O8/c1-6(28)15(29)23-14-12(19)9(16(30)21-7(2-24)3-25)11(18)10(13(14)20)17(31)22-8(4-26)5-27/h6-8,24-28H,2-5H2,1H3,(H,21,30)(H,22,31)(H,23,29)/t6-/m0/s1
Smiles
C(=O)(NC(CO)CO)c1c(c(C(=O)NC(CO)CO)c(c(c1I)NC(=O)[C@H](C)O)I)I

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 35gm/kg (35000mg/kg)   Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977.
man TDLo intraspinal 214uL/kg (0.214mL/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
American Journal of Emergency Medicine. Vol. 12, Pg. 329, 1994.
man TDLo intravenous 600mg/kg/3S-C (600mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

CARDIAC: CHANGE IN RATE
Archives of Internal Medicine. Vol. 147, Pg. 2208, 1987.
man TDLo intravenous 1657mg/kg (1657mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Annals of Internal Medicine. Vol. 107, Pg. 116, 1987.
mouse LD50 intracrebral 3gm/kg (3000mg/kg)   Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977.
mouse LD50 intraperitoneal 40825mg/kg (40825mg/kg)   United States Patent Document. Vol. #4001323,
mouse LD50 intravenous 33gm/kg (33000mg/kg) SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
mouse LD50 oral > 49gm/kg (49000mg/kg)   Drugs in Japan Vol. -, Pg. 104, 1990.
mouse LD50 subcutaneous > 49gm/kg (49000mg/kg)   Drugs in Japan Vol. -, Pg. 104, 1990.
rabbit LD50 intravenous 20gm/kg (20000mg/kg)   Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977.
rabbit LD50 parenteral 510mg/kg (510mg/kg)   United States Patent Document. Vol. #4001323,
rabbit LD50 unreported > 245mg/kg (245mg/kg)   Journal of the American College of Toxicology. Vol. 9, Pg. 563, 1990.
rat LD oral > 49gm/kg (49000mg/kg)   Farmaco, Edizione Scientifica. Vol. 32, Pg. 835, 1977.
rat LD50 intraarterial 13268mg/kg (13268mg/kg)   United States Patent Document. Vol. #4001323,
rat LD50 intracrebral 2449mg/kg (2449mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 200, 1995.
rat LD50 intraperitoneal 35gm/kg (35000mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 12(Suppl,
rat LD50 intravenous 22044mg/kg (22044mg/kg)   Acta Radiologica, Supplementum. Vol. 370, Pg. 41, 1987.
rat LD50 subcutaneous > 49gm/kg (49000mg/kg)   Drugs in Japan Vol. -, Pg. 104, 1990.
rat LDLo parenteral 2041mg/kg (2041mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 22, Pg. 769, 1994.

Specification

  Iopamiron , with CAS number of 60166-93-0, can be called (S)-N,N'-bis(2-Hydroxy-1-(hydroxymethyl)ethyl)-2,4,6-triiodo-5-lactamidoisophthalamide ; 1,3-Benzenedicarboxamide, N,N'-bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydroxy-1-oxopropyl)amino)-2,4,6-triiodo-, (S)- ; Iopamidol-200 in plastic container ; L-(+)-N,N'-Bis(2-hydroxy-1-hydroxymethylethyl)-2,4,6-triiodo-5-lactamide isophthalamide ; L-5alpha-Hydroxypropionylamino-2,4,6-triiodoisophthalic acid di(1,3-dihydroxy-2-propylamide) ; L-5alpha-Idrossipropionilamino-2,4,6-triiodoisoftal-di(1,3-diidrossi-2-propilamide) . It is a white crystalline powder, used as nonionic radiocontrast medium.