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Home > Encyclopedia > Indigo carmine

Indigo carmine

pharmaceutical raw materials
Indigo carmine structure

Indigo carmine 

structure
  • CAS No:

    860-22-0

  • Formula:

    C16H10N2O8S2.2Na

  • Chemical Name:

    Indigo carmine

  • Synonyms:

    1H-Indole-5-sulfonic acid,2-(1,3-dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene)-2,3-dihydro-3-oxo-,sodium salt (1:2);[Δ2,2′-Biindoline]-5,5′-disulfonic acid,3,3′-dioxo-,disodium salt;C.I. Acid Blue 74;1H-Indole-5-sulfonic acid,2-(1,3-dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene)-2,3-dihydro-3-oxo-,disodium salt;1311 Blue;12070 Blue;C.I. 73015;C.I. 75781;Acid Blue W;Acid Leather Blue IC;Airedale Blue IN;Amacid Brilliant Blue;Aniline Carmine Powder;Atul Indigo Carmine;FD & C Blue 2;A.F. Blue No. 2;Bucacid Indigotine B;Canacert Indigo Carmine;Carmine Blue;Cilefa Blue R;C.I. Food Blue 1;C.I. Natural Blue 2;Dolkwal Indigo Carmine;Edicol Supra Blue X;Food Blue 1;Grape Blue A;HD Indigo Carmine;HD Indigo Carmine Supra;Hexacert Blue No. 2;Hexacol Indigo Carmine Supra;Indigo carmine;Indigo Carmine A;Indigo Carmine AC;Indigo Carmine BP;Indigo Carmine Conc. FQ;Indigo Carmine Powder;Indigo Extract;Indigo Carmine X;Indigotine B;Indigotine I;Indigotine N;Indigotine Blue LZ;Indigotine disodium salt;Indigotine Extra Pure A;Indigotine Lake;Indocarmine F;Intense Blue;Maple Indigo Carmine;Mitsui Indigo Carmine;San-ei Indigo Carmine;Sodium 5,5′-indigotindisulfonate;Soluble indigo;Sumitomo Wool Blue SBC;Usacert Blue No. 2;FD and C Blue No. 2;Indigotine IA;Sodium 5,5′-indigodisulfonate;Disodium 5,5′-indigodisulfonate;L Blue Z 5010;Disodium 5,5′-indigotin disulfonate;Soluble indigo blue;Acid Blue 74;Food Blue No. 1;FD&C Blue No. 2;Indigotine Carmine;Indigotine;E 132;Indigotin (solubilized);Indigotin;5,5′-Indigodisulfonic acid disodium salt;Japan Blue 2;FD and C Blue 2;Usacert FD and C Blue No. 2;Ariavit Indigo Carmine;Food Blue No. 2;Food Blue 2;Indigo carmine NB;WAS 35;Sepisperse Dry 1003;Indigo Carmine 37006;Indigo Carmine 307019;Water Blue 177558;Water Blue 177557;FD & C Blue No 2-307045;Usacert FD & C Blue No 2-310118;Necol Indigo Carmine;Indigo Carmine 36009;Neelicol Indigo Carmine;Eurocert Indigo Carmine 311811;FD&C Blue No. 2-37006;Basovit Blue 665E;Cogilor Blue 511.11;Blue 2;

  • Categories:

    Cosmetic Ingredient  >  Cosmetic Colorant

Description

purple powder FD & C Blue No. 2 is principally the disodium salt of 2-( 1,3-dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene)-2,3-dihydro3-oxo-lH-indole-5-sulfonic acid.
The colorant is a blue-brown to red-brown powder that dissolves in water to give a solution that is blue at neutrality, blue-violet in acid, and green to yellow-green in base. When dissolved in concentrated sulfuric acid, it yields a blue-violet solution that turns blue when diluted with water. It is soluble in 95% ethanol.
FD


Indigo to dark blue powder. (NTP, 1992)


Indigo to dark blue powder. (NTP, 1992)|Indigo carmine is an organic sodium salt resulting from the formal condensation of indigo carmine (acid form) with two equivalents of sodium hydroxide. It is an indicator at pH 11.5-14, changing from blue to yellow. It has a role as a food colouring, a histological dye and a two-colour indicator. It contains an indigo carmine(2-).|Indigotindisulfonate Sodium is the sodium salt form of indigotindisulfonate, a synthetic blue dye and food colorant derived from indigo, that can be used as a stain in medical imaging and as a redox and pH indicator. Upon intravenous administration, indigotindisulfonate is filtered rapidly by the kidneys from the blood and colors the urinary tract which enables the urinary tract to be seen during surgery. It can also be used ex vivo to stain certain specimens, differentiate between benign and malignant lesions, and help stage and diagnose certain types of cancers.|Indolesulfonic acid used as a dye in renal function testing for the detection of nitrates and chlorates, and in the testing of milk.

Indigo carmine Basic Attributes

466.35

465.951752

4103904

212-728-8

D3741U8K7L

DTXSID1020190|DTXSID6044224|DTXSID0044288

C83799

Purple powder|Dark blue powder with coppery luster|Blue-red to red-brown powder or dark blue solid

V - Various

2933990090

Characteristics

189.36000

3.06060

Very dark blue to purple Powder/Solid

1.01 g/mL at20 °C

>300°C

n20/D1.335

H2O: 1 g/100 mL (25 ºC)

Store below +30°C.

LD50 orally in Rabbit: > 2000 mg/kg

Solutions have a blue or bluish-purple color ... The color is easily discharged by nitric acid, chlorates, etc; color of the aqueous solution fades on standing. Very sensitive to oxidizing agents|When heated to decomposition ... emits very toxic fumes of SOx, NOx, and Na2O

Water soluble.

Amines, Phosphines, and Pyridines

Sensitive to light. Very sensitive to oxidizing agents. Color is readily discharged by nitric acid, chlorates, etc. Color of aqueous solutions fades on standing. (NTP, 1992)

Safety Information

NONH for all modes of transport

3

22-36/37/38

22-24/25-36/37/39-27-26

DU3000000

Xn,Xi

Stable. Incompatible with strong oxidizing agents.

P264, P270, P301+P312, P330, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

All batches of this color additive when used for coloring foods (including dietary supplements) shall meet the specifications, uses and restrictions, and labeling regulations contained in 21 CFR Part 74 and be certified in accordance with regulations in 21 CFR Part 80.

Flash point data for this compound is not available, but it is probably combustible. (NTP, 1992)

|Warning|H302 (94.51%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 310 companies from 6 notifications to the ECHA C&L Inventory.

Fires involving this material can be controlled with a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

LD50 Rat iv 93 mg/kg

/A case of severe hypotension and bradycardia following intravenous indigo carmine injection in a patient with known sulfa allergy /is reported/.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 9,691 workers (3,035 of these were female) were potentially exposed to FD&C Blue No. 2 in the US(1).

Drug Information

The blue dye indigo carmine (sodium indigotindisulfonate) is administered intravascularly in a variety of treatments: to locate ureteral orifices (1), to endoscopically examine gastric cancer (2), and to adjust the position of a catheter in the chemotherapy of hepatic tumors (3) and of oralmaxillo-facial tumors.|Indigo carmine (sodium indigotindisulfonate) is a blue dye routinely administered IV during urologic and gynecologic procedures to localize the ureteral orifices.

... Severe hypotension /occurred/ in a patient who received vaginal administration of indigo carmine (IC). The severe hypotension observed seemed to have been induced by vasodilation rather than cardiac depression resulting from IC because of increased HR. Although IC's structural similarity to 5-hydroxytryptamine has previously been referred to a hypertensive and bradycardic episode caused by IC , /it was/ speculated that vasodilative substances such as NO might be released by IC in /the/ patient. When IC is given IV and IM in patients with normal renal function, it appears in urine after 5-7 min and 20-30 min, respectively. The appearance of IC in the patient urine should suggest that surgical manipulation for multiple submucosal myoma could damage the endometrium, and thus predisposed local absorption of IC. Although the mechanism for hypotension with IC is unclear, we should be aware that IC, when given vaginally as well as IV, could cause severe hypotension. Because of its known adverse effects, vaginal IC should not be considered totally safe.|... 4 patients ... had facial color changes to a blue-green-gray color and decreased oxygen saturation as measured by pulse oximetry. Patient 1 received an intravenous (IV) methylene blue solution during a urologic procedure, and the remaining three patients were administered subcutaneous indigo carmine (patient 2) or Patent Blue (Patients 3 and 4) for axillary lymph node mapping. All patients had above normal methemoglobin levels. Two (Patients 2 and 3) had hypotension, and one (Patient 3) required IV ephedrine to restore hemodynamic stability. Patient 4 had a hypersensitivity reaction characterized by systemic urticaria and blue-colored subintegumentary edema due to the subcutaneous administration.|... A case of severe hypotension and bradycardia following intravenous indigo carmine injection in a patient with known sulfa allergy /is reported/.|The hemodynamic effects most often encountered on intravascular indigo carmine administration are increases in diastolic and systolic blood pressure (BP(, which usually elicit reflex decreases in stroke volume and heart rate (HR). In contrast, severe bradycardia without changes in BP occurred in /a/ patient who was administered indigo carmine intraarterially. /The authors/ had previously experienced similar severe bradycardia in three other patients; on injection of 3 mL of 0.8% indigo carmine into the superficial temporal artery during IV sedation, HR rapidly decreased from 62-74 bpm to 45- 52 bpm, but BP was not changed. After the HR was restored, 5 mL of saline was injected into the same artery, but no changes in hemodynamics were observed. Thus, bradycardia associated with indigo carmine does not always occur after hypertension... Sudden severe hypotension also occurs in an otherwise stable surgery when indigo carmine is injected IV. Hence, the effects of intravascularly injected indigo carmine on hemodynamics are variable and difficult to anticipate ...|For more Drug Warnings (Complete) data for Indigotindisulfonate sodium (11 total), please visit the HSDB record page.

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)

Indigo carmine was metabolized by cecal microflora /of rats/ to four [corrected] fluorescent metabolites with Rf values of 0.09, 0.27, 0.5 and 0.72 ...

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/CASE REPORTS/ ... A case of severe hypotension and bradycardia following intravenous indigo carmine injection in a patient with known sulfa allergy /is reported/.|/CASE REPORTS/ Although considered biologically inactive, /indigo carmine/ has been associated with hypotension when administered in the presence of lumbar epidural anesthesia using local anesthetics ... A case of severe hypotension after the administration of indigo carmine /is described in a patient under general anesthesia with no significant epidural sympathectomy.|/CASE REPORTS/ ... A case of severe life-threatening anaphylactoid reaction followed by cardiac arrest associated with intravenous indigo carmine injection /is described/.|/CASE REPORTS/ ... A life-threatening anaphylactoid reaction to indigo carmine that may have been due to either a drug allergy or to its intrinsic serotonergic properties /is described/.|For more Human Toxicity Excerpts (Complete) data for Indigotindisulfonate sodium (7 total), please visit the HSDB record page.

(delta-2,2'-biindole)-3,3'-dione

Indigo carmine Use and Manufacturing

Methods of Manufacturing

FD&C Blue No. 2 is obtained by heating indigo (or indigo paste) in the presence of sulfuric acid. The color additive is isolated and subjected to purification procedures. The indigo (or indigo paste) used above is manufactured by the fusion of N-phenylglycine (prepared from aniline and formaldehyde) in a molten mixture of sodamide and sodium and potassium hydroxides under ammonia pressure. The indigo is isolated and subjected to purification procedures prior to sulfonation.

Uses

Colorant for nylon, surgical sutures, foods and ingested drugs.As a reagent for functional kidney tests, for detection of nitrates, chlorates and in testing milk.


Dyes

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7624]

Marketed as a paste with water; the dye contents varying according to specification or requirements of the user. It almost always contains sodium chloride or sulfate used for "salting" it out.

Synthetic dye and pigment manufacturing|1H-Indole-5-sulfonic acid, 2-(1,3-dihydro-3-oxo-5-sulfo-2H-indol-2-ylidene)-2,3-dihydro-3-oxo-, sodium salt (1:2): ACTIVE|The color additive FD&C Blue No. 2 is principally the disodium salt of 2-(1,3-dihydro-3-oxo-5-sulfo-2 H-indol-2-ylidene)-2,3-dihydro-3-oxo-1 H-indole-5-sulfonic acid (CAS Reg. No. 860-22-0) with smaller amounts of the disodium salt of 2-(1,3-dihydro-3-oxo-7-sulfo-2 H-indol-2-ylidene)-2,3-dihydro-3-oxo-1 H-indole-5-sulfonic acid (CAS Reg. No. 54947-75-0) and the sodium salt of 2-(1,3-dihydro-3-oxo-2 H-indol-2-ylidene)-2,3-dihydro-3-oxo-1 H-indole-5-sulfonic acid (CAS Reg. No. 605-18-5).|Indigo is a natural dye which is obtained from Indigofera tinctoria (True Indigo) and Isatis tinctoria (Dyer's Woad) and has been used to color textiles in India, China, and Egypt for 4,000 years. /Indigo/

Cosmetics -> Cosmetic colorant; Hair dyeing

Computed Properties

Molecular Weight:466.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:1
Exact Mass:465.95174613
Monoisotopic Mass:465.95174613
Topological Polar Surface Area:197
Heavy Atom Count:30
Complexity:877
Covalently-Bonded Unit Count:3
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Not clearly described

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • BIOPHORE INDIA PHARMACEUTICALS PVT LTD

    United States United States
    Active
  • 積水メディカル株式会社

    Japan Japan
    Active
  • MACSEN DRUGS

    United States United States
    Active

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