1-Naphthyl isothiocyanate

Description

1-Napthylisothiocyanate is a toxic chemical that has been used to create experimental cholestasis in rodents. Laboratory studies have also shown that 1-napthylisothiocyanate can act as a chemoprotectant in rodents challenged with a tumorinducing agent such as phorbol-12 myristate 13-acetate.

Chemical Properties

white crystalline powder

Uses

1-Naphthyl isothiocyanate (NITC) can be used as a source of thiourea moiety to synthesize derivatives of calix[4]arenes to be used as anion acceptors. It can also be used for the synthesis of naphthyl substituted 1,2,4-triazoles and 1,3,4-thiadiazoles.

Uses

1-Naphthylisothiocyanate is used as an ingredient in insecticides. It is also found in cyanamide, which is used in many industrial applications. It is commonly used in medical and drug studies in animals as a model hepatotoxicant producing experimental cholestasis in rats and mice.

Uses

1-Naphthyl isothiocyanate is a tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function.

Definition

ChEBI: 1-naphthyl isothiocyanate is an isothiocyanate. It has a role as an insecticide. It derives from a hydride of a naphthalene.

General Description

Odorless white needles or powder. Tasteless.

Air & Water Reactions

1-Naphthyl isothiocyanate is moisture sensitive. . Undergoes slow hydrolysis. Insoluble in water.

Reactivity Profile

Isocyanates and thioisocyanates, such as 1-Naphthyl isothiocyanate, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Fire Hazard

Flash point data for 1-Naphthyl isothiocyanate is not available, but 1-Naphthyl isothiocyanate is probably combustible.

Environmental Fate

Naphthylisothiocyanate is moisture sensitive and insoluble in water. The hydrolysis rate is slow.

Purification Methods

Crystallise the isothiocyanate from hexane (1g in 9 mL). It forms white needles and is soluble in most organic solvents but is insoluble in H2O. It is absorbed through the skin and may cause dermatitis. [Cymmerman-Craig et al. Org Synth Coll Vol IV 700 1963, Beilstein 12 H 1244, 12 III 2948.]

Toxicity evaluation

1-Naphthylisothiocyanate causes separation of extracellular tight junctions that seal bile canaliculi, impairing bile formation. 1-Naphthylisothiocyanate inhibits microsomal drug-metabolizing activity. In rats, 1-naphthylisothiocyanteglutathione complex is formed in hepatocytes, then transported to the bile ducts, where it is released from the glutathione, and then selectively injures biliary epithelial cells, resulting in reduced bile flow.