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N⁴-Chloroacetylcytosine arabinoside

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N⁴-Chloroacetylcytosine arabinoside
Names

IUPAC name N-[1-(β-D-Arabinofuranosyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-2-chloroacetamide
Systematic IUPAC name 2-Chloro-N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide
Identifiers
CAS Number	113737-52-3
3D model (JSmol)	Interactive image
ChemSpider	2338731
PubChem CID	3081042
CompTox Dashboard(EPA)	DTXSID00921180
InChI InChI=1S/C11H14ClN3O6/c12-3-7(17)13-6-1-2-15(11(20)14-6)10-9(19)8(18)5(4-16)21-10/h1-2,5,8-10,16,18-19H,3-4H2,(H,13,14,17,20)/t5-,8-,9+,10-/m1/s1 Key: WEJWVQRPBCYTRE-STRWAFKBSA-N InChI=1/C11H14ClN3O6/c12-3-7(17)13-6-1-2-15(11(20)14-6)10-9(19)8(18)5(4-16)21-10/h1-2,5,8-10,16,18-19H,3-4H2,(H,13,14,17,20)/t5-,8-,9+,10-/m1/s1 Key: WEJWVQRPBCYTRE-STRWAFKBBD
SMILES c1cn(c(=O)nc1NC(=O)CCl)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
Properties
Chemical formula	C₁₁H₁₄ClN₃O₆
Molar mass	319.70 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

N⁴-Chloroacetylcytosine arabinoside is aGABA agonist^[1]^{[dubious –discuss]} and might be apro-drug forcytosine arabinoside, a chemotherapy medication.^[2]

References

^Li, S; Zhang, Y; Liu, H; Yan, Y; Li, Y (2008). "Identification and expression of GABAC receptor in rat testis and spermatozoa".Acta Biochimica et Biophysica Sinica.40 (8):761–7.doi:10.1111/j.1745-7270.2008.00453.x.PMID 18685793.
^M, Ariatti; PA, Jones. "N4-chloroacetylcytosine arabinoside--a possible pro-drug of cytosine arabinoside".Biochemistry International.15 (6). Biochem Int.ISSN 0158-5231.PMID 3440022.

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GABA receptor modulators

GABA_ATooltip γ-Aminobutyric acid A receptor

Positive modulators (abridged; seehere for a full list):α-EMTBL
Alcohols (e.g.,drinking alcohol,2M2B)
Anabolic steroids
Avermectins (e.g.,ivermectin)
Barbiturates (e.g.,phenobarbital)
Benzodiazepines (e.g.,diazepam)
Bromide compounds (e.g.,potassium bromide)
Carbamates (e.g.,meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g.,mefenamic acid)
Flavonoids (e.g.,apigenin,hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g.,etomidate)
Kava constituents (e.g.,kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,allopregnanolone,cholesterol,THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil),cyclopyrrolones (e.g.,zopiclone),imidazopyridines (e.g.,zolpidem),pyrazolopyrimidines (e.g.,zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g.,propofol)
Phenytoin
Piperidinediones (e.g.,glutethimide)
Propanidid
Pyrazolopyridines (e.g.,etazolate)
Quinazolinones (e.g.,methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,baicalin)
Stiripentol
Sulfonylalkanes (e.g.,sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g.,valerenic acid)
Volatiles/gases (e.g.,chloral hydrate,chloroform,diethyl ether,paraldehyde,sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Negative modulators:5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin,picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators:Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

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