Chloralose: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
m Chembox: remove/replace depecated parameters; fix unk parameters (via AWB script)
outdated/replaced by GHS
 
(42 intermediate revisions by 25 users not shown)
Line 5: Line 5:
| ImageFile = Chloralose structure.svg
| ImageFile = Chloralose structure.svg
| ImageFile_Ref = {{Chemboximage|correct|CAS}}
| ImageFile_Ref = {{Chemboximage|correct|CAS}}
⚫
| ImageCaption = Structural formula of α-chloralose
| ImageSize = 200px
| ImageFile1 = Chloralose-from-xtal-3D-ball-and-stick.png
⚫
| ImageName = Stetreo structural formula of chloralose
| ImageCaption1 = Ball-and-stick model of α-chloralose
| IUPACName = (5ξ)-1,2-''O''-[2,2,2-Trichloroethylidene]-α-''xylo''-hexofuranose
| IUPACName = 1,2-''O''-[(1''R'')-2,2,2-Trichloroethane-1,1-diyl]-α-<small>D</small>-glucofuranose
| SystematicName = <!-- 1-[6-Hydroxy-2-(trichloromethyl)-tetrahydro-2''H''-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol -->
| SystematicName = (1''R'')-1-[(2''R'',3a''R'',4''S'',5''R'',6a''R'')-2-(Trichloromethyl)-tetrahydro-2''H''-furo[2,3-''d''][1,3]dioxol-5-yl]ethane-1,2-diol
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 238BZ29MUE
| UNII = 238BZ29MUE
| CASNo = 15879-93-3
| CASNo = 15879-93-3
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|correct|EBI}}
| ChEBI = 81902
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 2104181
| ChEMBL = 2104181
| PubChem = 7057995
| PubChem = 7057995
Line 27: Line 29:
| PubChem5 = 2723807
| PubChem5 = 2723807
| PubChem5_Comment = <small>(2''R'',3a''R'',5''R'',6''S'',6a''R'')-6-hydroxy-2-methyl-furo-5-yl</small>
| PubChem5_Comment = <small>(2''R'',3a''R'',5''R'',6''S'',6a''R'')-6-hydroxy-2-methyl-furo-5-yl</small>
| PubChem6 = 85991
| PubChemOther = 85991
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5414376
| ChemSpiderID = 5414376
Line 41: Line 43:
| Beilstein = 85418
| Beilstein = 85418
| RTECS = FM9450000
| RTECS = FM9450000
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C18707
| KEGG = C18707
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=8 | H=11 | Cl=3 | O=6
| C=8 | H=11 | Cl=3 | O=6
| MeltingPtC = 176 to 182}}
| MeltingPtC = 176 to 182}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| EUIndex = 605-013-00-0
| EUClass = {{Hazchem Xn}}
| MainHazards = Harmful if swallowed<br />
| MainHazards = Harmful if swallowed<br />
Harmful if inhaled
Harmful if inhaled
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS09}}
| RPhrases = {{R20/22}}
| GHSSignalWord = Danger
| SPhrases = {{S2}} {{S16}} {{S24/25}} {{S28}}
| HPhrases = {{H-phrases|301|332|336|410}}
| PPhrases = {{P-phrases|261|264|270|271|273|301+310|304+312|304+340|312|321|330|391|403+233|405|501}}
}}
}}
|Section8={{Chembox Related
|Section8={{Chembox Related
Line 59: Line 61:
}}
}}


'''Chloralose''' is an [[avicide]], [[rodenticide]] used to kill mice in temperatures below 15&nbsp;°C. It is also widely used in neuroscience and veterinary medicine as an [[anesthetic]] and [[sedative]].<ref>{{cite journal |author=Silverman J, Muir WW |title=A review of laboratory animal anesthesia with chloral hydrate and chloralose |journal=Lab Anim Sci. |volume=43 |issue=3 |pages=210–6 |date=Jun 1993 |pmid=8355479 }}</ref>
'''Chloralose''' (also known as α-chloralose) is an [[avicide]], and a [[rodenticide]] used to kill mice in temperatures below 15&nbsp;°C. It is also widely used in [[neuroscience]] and veterinary medicine as an [[anesthetic]] and [[sedative]].<ref>{{cite journal |author=Silverman J, Muir WW |title=A review of laboratory animal anesthesia with chloral hydrate and chloralose |journal=Lab Anim Sci. |volume=43 |issue=3 |pages=210–6 |date=Jun 1993 |pmid=8355479 }}</ref> Either alone or in combination, such as with [[Ethyl carbamate|urethane]], it is used for long-lasting, but light anesthesia.<ref>{{Citation|last=Vogler|first=George A.|title=Chapter 19 - Anesthesia and Analgesia|date=2006-01-01|url=https://www.sciencedirect.com/science/article/pii/B9780120749034500224|work=The Laboratory Rat (Second Edition)|pages=627–664|editor-last=Suckow|editor-first=Mark A.|series=American College of Laboratory Animal Medicine|place=Burlington|publisher=Academic Press|language=en|isbn=978-0-12-074903-4|access-date=2021-03-21|editor2-last=Weisbroth|editor2-first=Steven H.|editor3-last=Franklin|editor3-first=Craig L.}}</ref>


Chemically, it is a [[chlorine|chlorinated]] [[acetal]] derivative of [[glucose]].
Chemically, it is a [[chlorine|chlorinated]] [[acetal]] derivative of [[glucose]].


Chloralose exerts [[barbiturate]]-like actions on [[synaptic transmission]] in the brain, including potent effects at inhibitory [[GABAA receptor|γ-aminobutyric acid type A receptors]] (GABA<sub>A</sub>R).<ref>{{Cite journal | author = R. A. Nicoll & J. M. Wojtowicz | title = The effects of pentobarbital and related compounds on frog motoneurons | journal = [[Brain Research]] | volume = 191 | issue = 1 | pages = 225–237 | year = 1980 | doi = 10.1016/0006-8993(80)90325-x | pmid = 6247012| s2cid = 21777453 }}</ref><ref>{{Cite journal | author = K. M. Garrett & J. Gan | title = Enhancement of gamma-aminobutyric acidA receptor activity by alpha-chloralose | journal = [[The Journal of Pharmacology and Experimental Therapeutics]] | volume = 285 | issue = 2 | pages = 680–686 | year = 1998 | pmid = 9580613}}</ref> A structural isomer of chloralose, β-chloralose (also called parachloralose in older literature), is inactive as a GABA<sub>A</sub>R modulator and also as a general anesthetic.<ref>{{Cite journal | author = M. D. Krasowski & N. L. Harrison | title = The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations | journal = [[British Journal of Pharmacology]] | volume = 129 | issue = 4 | pages = 731–743 | year = 2000 | doi = 10.1038/sj.bjp.0703087 | pmid = 10683198| pmc = 1571881 }}</ref>
It is listed in Annex I of [[Directive 67/548/EEC]] with the classification ''Harmful'' ('''Xn''')

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.<ref>{{Cite news|date=2020-07-26|title=Poisoned bird had enough toxin to 'kill a child'|language=en-GB|work=BBC News|url=https://www.bbc.com/news/uk-england-york-north-yorkshire-53543989|access-date=2020-07-26}}</ref>


==References==
==References==
{{reflist}}
{{reflist}}



{{Hypnotics and sedatives}}
{{Hypnotics and sedatives}}
Line 82: Line 86:
[[Category:Sedatives]]
[[Category:Sedatives]]
[[Category:General anesthetics]]
[[Category:General anesthetics]]
[[Category:Trichloromethyl compounds]]
[[Category:Heterocyclic compounds with 2 rings]]
[[Category:Oxygen heterocycles]]




{{nervous-system-drug-stub}}
{{sedative-stub}}

Latest revision as of 16:32, 16 May 2024

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
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
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful if swallowed

Harmful if inhaled

GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H301, H332, H336, H410
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 checkY☒N ?)

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 (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[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.


Stub icon

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

Retrieved from "https://en.wikipedia.org/w/index.php?title=Chloralose&oldid=1224161830"