Chemistry:Chloralose

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Chloralose
Structural formula of α-chloralose
Names
IUPAC name
1,2-O-[(1R)-2,2,2-Trichloroethane-1,1-diyl]-α-D-glucofuranose
Systematic IUPAC name
(1R)-1-[(2R,3aR,4S,5R,6aR)-2-(Trichloromethyl)-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
Identifiers
3D model (JSmol)
85418
ChEBI
ChEMBL
ChemSpider
EC Number
  • 240-016-7
KEGG
MeSH Chloralose
  • 7057995
  • 40467114 (2R,3aR,5R,6R)-6-hydroxy-2-methyl-furo-5-yl
  • 27525 (2R,5R,6S,6aR)-6-hydroxy-2-methyl-furo-5-yl
  • 16211632 (1R)-dioxol, (2R,5R,6S,6aR)-6-hydroxy-2-methyl-furo-5-yl
  • 186624 (1R)-dioxol, (3aR,5R,6S,6aR)-6-hydroxy-furo-5-yl
  • 2723807 (2R,3aR,5R,6S,6aR)-6-hydroxy-2-methyl-furo-5-yl
  • 85991
RTECS number
  • FM9450000
UNII
Properties
C8H11Cl3O6
Molar mass 309.52 g·mol−1
Melting point 176 to 182 °C (349 to 360 °F; 449 to 455 K)
Hazards
Main hazards Harmful if swallowed

Harmful if inhaled

GHS pictograms GHS06: ToxicGHS07: HarmfulGHS09: Environmental hazard
GHS Signal word Danger
H301, H332, H336, H410
P261, P264, P270, P271, P273, P301+310, P304+312, P304+340, P312, P321, P330, P391, P403+233, P405, P501
Related compounds
Related compounds
Chloral hydrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chloralose (also known as α-chloralose) is an avicide, and a rodenticide used to kill mice in temperatures below 15 °C. It is also widely used in neuroscience and veterinary medicine as an anesthetic and sedative.[1] Either alone or in combination, such as with urethane, it is used for long-lasting, but light anesthesia.[2]

Chemically, it is a chlorinated acetal derivative of glucose.

It is listed in Annex I of Directive 67/548/EEC with the classification Harmful (Xn)

Chloralose exerts barbiturate-like actions on synaptic transmission in the brain, including potent effects at inhibitory γ-aminobutyric acid type A receptors (GABAAR).[3][4] A structural isomer of chloralose, β-chloralose (also called parachloralose in older literature), is inactive as a GABAAR modulator and also as a general anesthetic.[5]

Chloralose is often abused for its avicide properties. In the United Kingdom , protected birds of prey have been killed using the chemical. Legal use for bird control also often causes raptor mortalities from secondary poisoning, as well as primary poisoning of non-target species from eating bait, for example, kererū pigeon in New Zealand.[6]

References

  1. Silverman J, Muir WW (Jun 1993). "A review of laboratory animal anesthesia with chloral hydrate and chloralose". Lab Anim Sci. 43 (3): 210–6. PMID 8355479. 
  2. Vogler, George A. (2006-01-01), Suckow, Mark A.; Weisbroth, Steven H.; Franklin, Craig L., eds., "Chapter 19 - Anesthesia and Analgesia" (in en), The Laboratory Rat (Second Edition), American College of Laboratory Animal Medicine (Burlington: Academic Press): pp. 627–664, ISBN 978-0-12-074903-4, https://www.sciencedirect.com/science/article/pii/B9780120749034500224, retrieved 2021-03-21 
  3. R. A. Nicoll & J. M. Wojtowicz (1980). "The effects of pentobarbital and related compounds on frog motoneurons". Brain Research 191 (1): 225–237. doi:10.1016/0006-8993(80)90325-x. PMID 6247012. 
  4. K. M. Garrett & J. Gan (1998). "Enhancement of gamma-aminobutyric acidA receptor activity by alpha-chloralose". The Journal of Pharmacology and Experimental Therapeutics 285 (2): 680–686. PMID 9580613. 
  5. M. D. Krasowski & N. L. Harrison (2000). "The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations". British Journal of Pharmacology 129 (4): 731–743. doi:10.1038/sj.bjp.0703087. PMID 10683198. 
  6. "Poisoned bird had enough toxin to 'kill a child'" (in en-GB). BBC News. 2020-07-26. https://www.bbc.com/news/uk-england-york-north-yorkshire-53543989.