Carbazochrome Chemical Properties

Melting point:

203° (dec)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Water (Slightly, Heated)

pka

12.38±0.40(Predicted)

form 

Solid

color 

Dark Orange to Very Dark Orange

Water Solubility 

Water: 5 mg/mL (21.17 mM; ultrasonic and adjust pH to 12 with NaOH)

Merck 

14,172

Stability:

Hygroscopic

InChI

InChI=1S/C10H12N4O3/c1-14-4-9(16)5-2-6(12-13-10(11)17)8(15)3-7(5)14/h2-3,9,16H,4H2,1H3,(H3,11,13,17)

InChIKey

XSXCZNVKFKNLPR-UHFFFAOYSA-N

SMILES

N(C(N)=O)N=C1C(=O)C=C2C(=C1)C(O)CN2C

CAS DataBase Reference

69-81-8(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

2

RTECS 

NM1925500

HS Code 

29339900

Storage Class

11 - Combustible Solids

Carbazochrome Usage And Synthesis

Originator

Adrenosem,Beecham,US,1953

Uses

Carbazochrome is an oxidation product of Epinephrine [E588580]) that improves microcirculatory tone. Derivatives such as carbazochrome salicylate and carbazochrome sodium sulfonate, are used as hemostats and treatment to prevent dengue shock syndrome, respectively.

Definition

ChEBI: Carbazochrome is a member of indoles. It is functionally related to a semicarbazide.

Indications

Carbazochrome is indicated for capillary and parenchymal hemorrhage (trauma, tonsillectomy, during surgery), intestinal bleeding, and thrombocytopenic purpura.

Manufacturing Process

A suspension containing 1 part by weight of adrenalin and 2 to 6 parts by weight of silver oxide in 150 to 250 parts by weight of methanol or ethanol is stirred for about 10 minutes. The alcoholic adrenochrome solution obtained is separated by draining and the filtrate is quickly evaporated to dryness at low temperature and in vacuo. The red crystals of adrenochrome obtained are dissolved in 45 to 55 parts by weight of water. To this solution, 2 parts of sodium acetate dissolved in 2 to 3 parts of water and 2 parts of semicarbazide hydrochloride dissolved in 2 to 3 parts of water are added. The formed precipitate consisting of red-orange prismatic needles is separated by filtration and recrystallized from diluted ethanol. There is obtained 0.30 to 0.40 part by weight of adrenochrome monosemicarbazone dihydrate, melting at 203°C with decomposition.

Therapeutic Function

Hemostatic

Side effects

The common side effects of carbazochrome includes skin rashes, gastrointestinal disturbances (nausea, abdominal pain), and injection site pain. Rarely, it may cause hypersensitivity, dizziness, or headache.

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