Chloralose

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Chloralose
Structural formula of α-chloralose
Names
IUPAC name
1,2-O-[(1R)-2,2,2-Trichloroethane-1,1-diyl]-α-D-glucofuranose
Preferred 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
ECHA InfoCard 100.036.363 Edit this at Wikidata
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
  • InChI=1S/C8H11Cl3O6/c9-8(10,11)7-16-5-3(14)4(2(13)1-12)15-6(5)17-7/h2-7,12-14H,1H2/t2-,3+,4-,5-,6-,7-/m1/s1 checkY
    Key: OJYGBLRPYBAHRT-IPQSZEQASA-N checkY
  • InChI=1/C8H11Cl3O6/c9-8(10,11)7-16-5-3(14)4(2(13)1-12)15-6(5)17-7/h2-7,12-14H,1H2/t2-,3+,4-,5-,6-,7-/m1/s1
    Key: OJYGBLRPYBAHRT-IPQSZEQABF
  • 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
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, H400, 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).
☒N verify (what is checkY☒N ?)
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 using for bird control also often causes raptor mortalities from secondary poisoning, as well as primary poisoning of non-target speciea from eating bait, for example, kereru pigeon in New Zealand. [6]

References[edit]

  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", The Laboratory Rat (Second Edition), American College of Laboratory Animal Medicine, Burlington: Academic Press, pp. 627–664, ISBN 978-0-12-074903-4, 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. S2CID 21777453.
  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. PMC 1571881. PMID 10683198.
  6. ^ "Poisoned bird had enough toxin to 'kill a child'". BBC News. 2020-07-26. Retrieved 2020-07-26.