alpha-Chloralose
[CAS# 15879-93-3]

Identification

• Classification: API >> Anesthetic agents >> General anesthetics
• Name: alpha-Chloralose
• Synonyms: 1,2-O-(2,2,2-Trichloroethylidene)-alpha-D-glucofuranose
• Molecular Formula: C₈H₁₁Cl₃O₆
• Molecular Weight: 309.53
• CAS Registry Number: 15879-93-3
• EC Number: 240-016-7
• SMILES: C([C@H]([C@@H]1[C@@H]([C@@H]2[C@H](O1)O[C@@H](O2)C(Cl)(Cl)Cl)O)O)O

Properties

• Solubility: 0.44 g/100 mL (water, 15 °C), 46 mg/mL (DMSO) (Expl.)
• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 178-182 °C (Expl.)
• alpha: 18 ° (c=2, 95% C2H5OH)
• Index of Refraction: 1.587, Calc.^*
• Boiling Point: 504.4±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 258.9±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS09 Danger
• Risk Statements: H301-H302-H312-H332-H336-H400-H410
• Safety Statements: P261-P264-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P317-P319-P321-P330-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H336
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

Alpha-chloralose is a chemical compound that has gained recognition for its use as a rodenticide, anesthetic, and in certain laboratory research settings. It is a chlorinated derivative of glucose, consisting of a glucose molecule with a chlorine atom substituted at the alpha position of the glucose ring. This substance is known for its ability to act as a central nervous system depressant, and it is primarily used in the control of rodent populations due to its high toxicity to mammals.

The discovery of alpha-chloralose dates back to the early 20th century. It was first synthesized in 1928 by chemists who were investigating the effects of various chlorinated sugar derivatives on biological systems. Researchers soon realized that alpha-chloralose had potent anesthetic and sedative properties, leading to its further development and use in both medical and agricultural applications. Its rodenticide properties were particularly valuable, as it provided an effective and relatively humane method of controlling rodent populations without causing excessive harm to non-target animals when used correctly.

As a rodenticide, alpha-chloralose is commonly used in pest control, particularly in areas where rodent infestations are problematic. Its mechanism of action involves inhibiting the central nervous system, leading to paralysis and death in rodents. It works by disrupting the function of neurotransmitters in the brain, causing the rodent to become immobilized and eventually succumb to respiratory failure. Alpha-chloralose has been found to be more selective for rodents compared to other mammals, making it an effective tool in controlling pests while minimizing the impact on non-target species. However, it is still considered a highly toxic substance and must be used with care, especially in agricultural and urban settings.

In addition to its use as a rodenticide, alpha-chloralose is employed in medical and research settings as a general anesthetic. It has been used in certain surgical procedures, especially in veterinary medicine, to induce sedation and anesthesia in small animals. Its ability to induce a deep, reversible sedation has made it useful in studies involving small mammal models, particularly in the fields of pharmacology and toxicology. Alpha-chloralose is sometimes used in behavioral research, as it can immobilize subjects for various experiments without the need for more invasive methods of anesthesia.

One of the challenges associated with alpha-chloralose is its narrow therapeutic window. While it is effective as a rodenticide and anesthetic, its margin of safety between therapeutic and toxic doses is relatively small. This means that accidental poisoning of non-target species or humans can occur if the substance is not handled carefully. To mitigate these risks, precautions are necessary when using alpha-chloralose in both laboratory and field settings, including careful dosage monitoring and protective measures.

In agriculture, alpha-chloralose has also been used as a tool in managing wildlife that may damage crops. By targeting pest species such as rats and mice, it helps protect the agricultural industry, particularly in regions where rodents are known to cause significant economic losses. However, its use is regulated due to concerns about environmental contamination and the potential for secondary poisoning of animals that consume the poisoned rodents.

Alpha-chloralose remains a useful but carefully regulated compound in pest control and research. Ongoing research into its efficacy, safety, and alternative methods of application continues to be important to ensure its responsible use. As new techniques and formulations are developed, alpha-chloralose may continue to serve as a valuable tool in both pest management and scientific investigation.

References

1970. [Human intoxication by chloralose. Clinical study and electroencephalography]. Acta neurologica Belgica, 70(3), 377-392.
URL: https://pubmed.ncbi.nlm.nih.gov/4990666

1979. N-Allyl-derivative of clonidine, a substance with specific bradycardic action at a cardiac site. Naunyn-Schmiedeberg's Archives of Pharmacology, 306(3), 225-232.
DOI: https://pubmed.ncbi.nlm.nih.gov/471078

2024. Blood Flow Changes in the Rabbit Cranial and Caudal Venae Cavae during Postural Loads after Propranolol, Bisoprolol and Methyldopa Pretreatment. Journal of Evolutionary Biochemistry and Physiology, 60(3), 1056-1068.
DOI: 10.1134/s0022093024030050