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
CAS Number
3D model (JSmol )
Beilstein Reference
85418
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.036.363
EC Number
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
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
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
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
C 8 H 11 Cl 3 O 6
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 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 (what is Y N ?)
Infobox references
Chemical compound
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 (GABAA R).[3] [4] A structural isomer of chloralose, β-chloralose (also called parachloralose in older literature), is inactive as a GABAA R 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 [ ]
^ 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 .
Hypnotics /sedatives (N05C )
GABAA
Alcohols Barbiturates Benzodiazepines
Brotizolam
Cinolazepam
Climazolam
Clonazepam
Doxefazepam
Estazolam
Flunitrazepam
Flurazepam
Flutoprazepam
Lorazepam
Loprazolam
Lormetazepam
Midazolam
Nimetazepam
Nitrazepam
Phenazepam
Quazepam
Temazepam
Triazolam
Carbamates Imidazoles Monoureides Neuroactive steroids Nonbenzodiazepines Phenols Piperidinediones Quinazolinones Others
GABAB
1,4-Butanediol
4-Fluorophenibut
Aceburic acid
Baclofen
GABOB
GHB (sodium oxybate )
GBL
GVL
Phenibut
Tolibut
H1
Antihistamines
Captodiame
Cyproheptadine
Diphenhydramine
Doxylamine
Hydroxyzine
Methapyrilene
Perlapine
Pheniramine
Promethazine
Propiomazine
Antidepressants
Serotonin antagonists and reuptake inhibitors
Etoperidone
Nefazodone
Trazodone
Tricyclic antidepressants
Amitriptyline
Doxepin
Trimipramine , etc.
Tetracyclic antidepressants
Antipsychotics
Typical antipsychotics
Chlorpromazine
Thioridazine , etc.
Atypical antipsychotics
α2 -Adrenergic
Clonidine
Detomidine
Dexmedetomidine
Lofexidine
Medetomidine
Romifidine
Tizanidine
Xylazine
5-HT2A
Antidepressants
Trazodone
Tricyclic antidepressants
Amitriptyline
Doxepin
Trimipramine , etc.
Tetracyclic antidepressants
Antipsychotics
Typical antipsychotics
Chlorpromazine
Thioridazine , etc.
Atypical antipsychotics
Others
Melatonin Orexin α2 δ VDCC
Gabapentin
Gabapentin enacarbil
Mirogabalin
Phenibut
Pregabalin
Others
Cannabidiol
Diethylpropanediol
Evoxine
Fenadiazole
Guaifenesin -related muscle relaxants
Chlorphenesin
Mephenesin
Mephenoxalone
Metaxalone
Methocarbamol
Midaflur
Opioids (e.g., morphine )
Passion flower
Scopolamine
Trazodone
UMB68
Valnoctamide
General anesthetics (N01A )
Inhalational
Chloroethane (ethyl chloride) ‡
Chloroform ‡
Cyclopropane ‡
Desflurane
Diethyl ether ‡
Enflurane
Ethylene ‡
Fluroxene ‡
Halothane #
Isoflurane #
Methoxyflurane
Methoxypropane ‡
Nitrous oxide #
Sevoflurane
Trichloroethylene ‡
Vinyl ether ‡
Xenon
Injection
Phenols Barbiturates Opioids
Morphine #
Oxycodone
Anileridine ‡
Embutramide ‡
Fentanyl #
Alfentanil
Phenoperidine
Remifentanil ÷
Sufentanil
Arylcyclohexylamines Neuroactive steroids Others
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Pest control : Rodenticides
Anticoagulants /Vitamin K antagonists
Coumarins /4-Hydroxycoumarins
1st generation 2nd generation (Superwarfarins )
Brodifacoum
Bromadiolone
Difenacoum
Flocoumafen
1,3-Indandiones
Chlorophacinone
Pindone
Diphacinone
Others
Convulsants
Crimidine
Phenylsilatrane
Strychnine
Tetramethylenedisulfotetramine
Chlorophenylsilatrane
Calciferols
Cholecalciferol
Ergocalciferol
Inorganic compounds
Aluminium phosphide
Arsenic
Barium carbonate
Calcium phosphide
Cyanide
Thallium sulfate
Zinc phosphide
Organochlorine Organophosphorus Respiratory toxins
Bromethalin
Fluoroacetamide
1,3-Difluoro-2-propanol (Gliftor)
Sodium fluoroacetate
Others
α-Naphthylthiourea
Norbormide
Pyrinuron
Scilliroside
Flupropadine
GABA A receptor positive modulatorsAlcohols
Butanol
Chloralodol
Chlorobutanol (cloretone)
Ethanol (alcohol) (alcoholic drink )
Ethchlorvynol
Isobutanol
Isopropanol
Menthol
Methanol
Methylpentynol
Pentanol
Petrichloral
Propanol
tert -Butanol (2M2P)
tert -Pentanol (2M2B)
Tribromoethanol
Trichloroethanol
Triclofos
Trifluoroethanol
Barbiturates Benzodiazepines Carbamates Flavonoids
Ampelopsin (dihydromyricetin)
Apigenin
Baicalein
Baicalin
Catechin
EGC
EGCG
Hispidulin
Luteolin
Skullcap constituents (e.g., baicalin )
Wogonin
Imidazoles Kava constituents
Desmethoxyyangonin
Kavain
Methysticin
Yangonin
Monoureides Neuroactive steroids Nonbenzodiazepines Phenols
Fospropofol
Propofol
Thymol
Piperidinediones Pyrazolopyridines Quinazolinones Volatiles /gases
Acetone
Acetophenone
Acetylglycinamide chloral hydrate
Aliflurane
Benzene
Butane
Butylene
Centalun
Chloral
Chloral betaine
Chloral hydrate
Chloroform
Cryofluorane
Desflurane
Dichloralphenazone
Dichloromethane
Diethyl ether
Enflurane
Ethyl chloride
Ethylene
Fluroxene
Gasoline
Halopropane
Halothane
Isoflurane
Kerosine
Methoxyflurane
Methoxypropane
Nitric oxide
Nitrogen
Nitrous oxide
Norflurane
Paraldehyde
Propane
Propylene
Roflurane
Sevoflurane
Synthane
Teflurane
Toluene
Trichloroethane (methyl chloroform)
Trichloroethylene
Vinyl ether
Others/unsorted
3-Hydroxybutanal
Avermectins (e.g., ivermectin )
Bromide compounds (e.g., lithium bromide , potassium bromide , sodium bromide )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
DEABL
Dihydroergolines (e.g., dihydroergocryptine , , dihydroergotamine , ergoloid (dihydroergotoxine) )
Efavirenz
Etazepine
Etifoxine
Fenamates (e.g., flufenamic acid , mefenamic acid , niflumic acid , tolfenamic acid )
Fluoxetine
Flupirtine
Hopantenic acid
Lanthanum
Lavender oil
Lignans (e.g., 4-O-methylhonokiol , honokiol , magnolol , obovatol )
Loreclezole
Menthyl isovalerate (validolum)
Monastrol
Niacin
Niacinamide
Org 25,435
Phenytoin
Propanidid
Retigabine (ezogabine)
Safranal
Seproxetine
Stiripentol
(e.g., sulfonmethane (sulfonal) , tetronal , trional )
Terpenoids (e.g., borneol )
Topiramate
Valerian constituents (e.g., isovaleric acid , isovaleramide , valerenic acid , )
Unsorted benzodiazepine site positive modulators: α-Pinene
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators