Chlorobutanol (trichloro-2-methyl-2-propanol) is a

preservative A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by ...

, sedative, hypnotic and weak

local anesthetic A local anesthetic (LA) is a medication that causes absence of pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general a ...

similar in nature to

chloral hydrate Chloral hydrate is a geminal diol with the formula . It is a colorless solid. It has limited use as a sedative and hypnotic pharmaceutical drug. It is also a useful laboratory chemical reagent and precursor. It is derived from chloral (trichl ...

. It has antibacterial and antifungal properties. Chlorobutanol is typically used at a concentration of 0.5% where it lends long term stability to multi-ingredient formulations. However, it retains antimicrobial activity at 0.05% in water. Chlorobutanol has been used in anesthesia and euthanasia of invertebrates and fishes. It is a white, volatile solid with a camphor-like odor.

Synthesis

Chlorobutanol was first synthesized in 1881 by the German chemist Conrad Willgerodt (1841–1930). Chlorobutanol is formed by the reaction of chloroform and

acetone Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscib ...

in the presence of

potassium Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmosph ...

or sodium hydroxide. It may be purified by sublimation or recrystallisation.

Toxicity

Chlorobutanol is highly toxic to the liver, is a skin irritant and a severe eye irritant.

Parthenogenesis

Chlorobutanol has proven effective at stimulating parthenogenesis in sea urchin eggs up to the pluteus stage, possibly by increasing irritability to cause stimulation. For the eggs of the fish ''

Oryzias latipes The Japanese rice fish (''Oryzias latipes''), also known as the medaka, is a member of genus ''Oryzias'' (ricefish), the only genus in the subfamily Oryziinae. This small (up to about ) native of East Asia is a denizen of rice paddies, marshes, ...

'', however, chlorobutanol only acted as an anesthetic.

Pharmacology

It is an anesthetic with effects related to isoflurane and halothane.

References

External links

Chlorobutanol MSDS
* {{Authority control Hypnotics Sedatives Trichloromethyl compounds Tertiary alcohols GABAA receptor positive allosteric modulators Glycine receptor agonists Halohydrins