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Other Classes -> Halogenated Alcohols

Other Classes -> Halogenated Alcohols

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Listed in ZINC15

log Kow= 2.03

2.03

Camphor odor

Characteristic odor

Camphor taste

Characteristic taste

NEEDLES (WATER+1)

Crystals

COLORLESS TO WHITE

Colorless to white crystals

INSOL IN COLD WATER, SOL IN HOT WATER

1 G IN 125 ML WATER; SOL IN VOLATILE OILS

Easily sol in hot water; one gram dissolves in 1 ml alcohol, 10 ml glycerol; sol in chloroform, ether, acetone, petr ether, glacial acetic acid, oils.

Soluble in alcohol and glycerol, hot water, ether, chloroform, and volatile oils.

For more Solubility (Complete) data for CHLORETONE (6 total), please visit the HSDB record page.

97 °C

MP: 77 °C (HYDRATE); HYGROSCOPIC

MP: 97 °C /anhydrous form/; MP: 78 °C /hemihydrate/

This chemical does not meet GHS hazard criteria for 1.5% (1 of 67) of reports.

Warning

H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P280, P301+P317, P302+P352, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: 2-Propanol, 1,1,1-trichloro-2-methyl-

Status: Active Update: 24-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/25631

2-Propanol, 1,1,1-trichloro-2-methyl-hydrate: Does not have an individual approval but may be used under an appropriate group standard

A skin and eye irritant; 0.4% solution caused keratitis in rabbit eyes following continuous bathing; Emergency treatment is for chloral hydrate and related agents. [HSDB]

See Chlorobutanol.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Chloretone is a chemical derivative of chloral, named in section 502(d) of the Federal Food, Drug, and Cosmetic Act and is hereby designated as habit forming.

Acute Tox. 4 (94%)

Acute Tox. 4 (100%)

IN GENERAL, MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED ... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED FROM EACH OTHER.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

...SOLN CONTAINING...0.4% CHLOROBUTANOL...UNDER CONTACT LENS...LEFT ON EYE FOR SEVERAL MIN...UNCOMFORTABLE KERATITIS EPITHELIALIS HAS RESULTED, WITH FOGGING OF VISION, HALOES AROUND LIGHTS, & FOREIGN-BODY TYPE OF DISCOMFORT BEGINNING WITHIN HR & BECOMING WORSE...EYES HAVE RECOVERED SPONTANEOUSLY & COMPLETELY IN DAY OR TWO.

This substance may be habit forming ...

EXPT ON EXCISED ANIMAL CORNEAS HAVE SHOWN THAT CHLOROBUTANOL INHIBITS OXYGEN UPTAKE & REDUCES ADHESION OF EPITHELIUM TO CORNEAL STROMA...

EXPT ON RABBITS...AFTER APPLICATION OF...LOCAL ANESTHETIC...BATHING EYES CONTINUOUSLY FOR 20 MIN WITH AQ SOLN CONTAINING...0.4% CHLOROBUTANOL PRODUCES DEFINITE KERATITIS EPITHELIALIS...IN CORNEA. ... FRESHLY PREPD SOLN @ PH 5.5 HAS CAUSED VISIBLE KERATITIS EPITHELIALIS AFTER 5 TO 10 MIN OF BATHING.

CHLOROBUTANOL CAUSED 30% DECR IN CONTRACTION AMPLITUDE & 20% INCR IN ACTION-POTENTIAL DURATION. LOWERED CONDUCTION VELOCITY & INDUCED CONDUCTION FAILURE & AUTOMATICITY WITHIN ISOLATED VENTRICULAR MUSCLE STRIPS.

INCR URINARY & HEPATIC CONCN OF D-GLUCURONIC ACID, L-ASCORBIC ACID, & D-GLUCARIC ACID WERE FOUND WITHIN 8 HR AFTER ADMIN OF CHLORBUTOL TO RATS.

MALE RATS KEPT ON NORMAL DIETS SUPPLEMENTED WITH CHLORETONE (0.04%) PRODUCED CHOLESTEROLEMIC ACTIVITY, SIGNIFICANT INCR IN URINARY EXCRETION OF ASCORBIC ACID WAS FOUND WITH COEFFICIENT OF ANILINE HYDROXYLASE ACTIVITY OF 0.84.

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Chloretone is a chemical derivative of chloral, named in section 502(d) of the Federal Food, Drug, and Cosmetic Act and is hereby designated as habit forming.

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Chlorobutanol is a detergent preservative with a broad spectrum of antimicrobial activity. _In vitro_, chlorobutanol demonstrated to inhibit platelet aggregation and release via unknown mechanisms. A study proposes that the antiplatelet effect of chlorobutanol may occur from inhibition of the arachidonic acid pathway. It attenuated thromboxane B2 formation, elevation of cytosolic free calcium, and ATP release, and additionally exhibited a significant inhibitory activity toward several aggregation inducers in a time- and concentration-dependent manner. Chlorobutanol may exert a direct negative inotropic effect on myocardial cells to isometric tension produced by the heart. Chlorobutanol was shown to induce conjunctival and corneal cell toxicity _in vitro_: at a concentration of 0.1%, Cbl caused near depletion of the squamous layer while degeneration of corneal epithelial cells, generation of conspicuous membranous blebs, cytoplasmic swelling, and occasional breaks in the external cell membrane were observed at a concentration of 0.5%.

As a detergent, chlorobutanol disrupts the lipid structure of the cell membrane and increases the cell permeability, leading to cell lysis. It induces conjunctival and corneal cell toxicity via causing cell retraction and cessation of normal cytokines, cell movement, and mitotic activity. It disrupts the barrier and transport properties of the corneal epithelium as well as inhibits the utilization of oxygen by the cornea. Chlorobutanol also inhibits oxygen use by the cornea, which increases susceptibility to infection.

Following oral administration in healthy subjects, the plasma concentration fell by 50% in 24 hours post-administration.

Under physiological conditions, chlorobutanol is unstable. The mean urinary recovery accounts for 9.6% of the dose orally administered.

The volume of distribution was approximately 233 ± 141 L in healthy individuals receiving oral chlorobutanol.

In healthy subjects, the clearance was approximately 11.6 ± 1.0 mL/min following oral administration.

Used as a plasticizer for cellulose esters and ethers, in medical practice (preservative, antimicrobial agent, anesthetic in dentistry, sedative and hypnotic, antiemetic), and in veterinary practice (antiseptic, local anesthetic, sedative, antiemetic, antipruritic, and hypnotic); [HSDB]

Using Disinfectants or Biocides [Category: Clean]

Plasticizer for cellulose esters and ethers; preservative for biological fluids, hypodermic soln and soln of alkaloids. Pharmaceutical aid (antimicrobial).

MEDICATION (VET)

MEDICATION

USED IN OPHTHALMIC PREPARATIONS

Prepn: prepd by action of powdered potassium hydroxide or of potassium ethoxide solution on mixture of chloroform & acetone ...

By action of potassium hydroxide on a solution of chloroform and acetone.

The para and ortho positions of phenols condense at the carbonyl group of acetone to make bisphenols... If the H atom is activated, ClCH- compounds add to the carbonyl group in the presence of stong base; chloroform gives chloretone.

CHLOROBUTANOL HAS BEEN WIDELY EMPLOYED AS VERY EFFECTIVE PRESERVATIVE IN EYEDROPS, USUALLY IN 0.5% CONCN, WITHOUT PRODUCING CLINICALLY RECOGNIZED OCULAR DISTURBANCE, EVEN THOUGH APPLIED SEVERAL TIMES A DAY FOR SEVERAL YR.

Chlorobutanol may be anhyd or it may contain up to about 1/2 mol of water. Label shall indicate whether chlorobutanol is anhyd or hydrate.

Grade: USP

Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients

Cosmetics -> Preservative

2-Propanol, 1,1,1-trichloro-2-methyl-: ACTIVE

2-Propanol, trichloro-2-methyl-: INACTIVE

REACTS WITH RUBBER (VIAL STOPPERS, ETC) & RAPIDLY LOSES POTENCY. ... FDA REGULATION MAKES ZERO RESIDUE MANDATORY IN MILK FOR HUMAN CONSUMPTION.

...DRUGS USED IN DOPING. ... AMONG DEPRESSANTS MAY BE MENTIONED...CHLORBUTOL...

BECAUSE OF DECOMP IN ALKALINE SOLN, WITH LOSS OF ANTIBACTERIAL ACTIVITY, IT IS UNSUITABLE FOR USE AS BACTERIOSTATIC AGENT IN SUCH SOLN. IT IS REPORTED TO BE SLOW-ACTING. ... CHLOROBUTANOL IS NEUTRALIZED OR INACTIVATED BY 10% OF TWEEN 20 IN NUTRIENT BROTH MEDIUM.

APPROX 25% OF COMMERCIAL OPHTHALMIC SOLN CONTAIN CHLOROBUTANOL, SOMETIMES WITH EDTA.