Chloralose

Chloralose
	; Structural formula of α-chloralose
	; Ball-and-stick model 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
CAS Number	15879-93-3 [EBI];
3D model (JSmol)	Interactive image;
Beilstein Reference	85418
ChEBI	CHEBI:81902;
ChEMBL	ChEMBL2104181 ;
ChemSpider	5414376 ;
ECHA InfoCard	100.036.363
EC Number	240-016-7;
KEGG	C18707 ;
MeSH	Chloralose
PubChem CID	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	238BZ29MUE ;
CompTox Dashboard (EPA)	DTXSID4020088 ;
	InChI 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 Key: OJYGBLRPYBAHRT-IPQSZEQASA-N ; 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;
	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
Chemical formula	C8H11Cl3O6
Molar mass	309.52 g·mol−1
Melting point	176 to 182 °C (349 to 360 °F; 449 to 455 K)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Harmful if swallowed; Harmful if inhaled
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H332, H336, H410
Precautionary statements	P261, P264, P270, P271, P273, P301+P310, P304+P312, P304+P340, P312, P321, P330, P391, P403+P233, 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). verify (what is ?) 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.

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

^ 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.
^ 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
^ 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.
^ 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.
^ 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.
^ "Poisoned bird had enough toxin to 'kill a child'". BBC News. 2020-07-26. Retrieved 2020-07-26.

This sedative-related article is a stub. You can help Wikipedia by expanding it.

[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.

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Names
Structural formula of α-chloralose
Ball-and-stick model of α-chloralose
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
CAS Number	15879-93-3^Y[EBI]
3D model (JSmol)	Interactive image
Beilstein Reference	85418
ChEBI	CHEBI:81902
ChEMBL	ChEMBL2104181^Y
ChemSpider	5414376^Y
ECHA InfoCard	100.036.363
EC Number	240-016-7
KEGG	C18707^Y
MeSH	Chloralose
PubChem CID	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	238BZ29MUE^Y
CompTox Dashboard (EPA)	DTXSID4020088
InChI 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^Y Key: OJYGBLRPYBAHRT-IPQSZEQASA-N^Y 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
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
Chemical formula	C₈H₁₁Cl₃O₆
Molar mass	309.52 g·mol⁻¹
Melting point	176 to 182 °C (349 to 360 °F; 449 to 455 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful if swallowed Harmful if inhaled
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H332, H336, H410
Precautionary statements	P261, P264, P270, P271, P273, P301+P310, P304+P312, P304+P340, P312, P321, P330, P391, P403+P233, 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 ^YN ?) Infobox references