Quinine arsenate

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	3C20H24N2O2.2AsH3O4
Molecular Weight	1257.1363
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[As](O)(O)=O.O[As](O)(O)=O.[H][C@]1(C[C@@H]2CCN1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3.[H][C@]5(C[C@@H]6CCN5C[C@@H]6C=C)[C@H](O)C7=C8C=C(OC)C=CC8=NC=C7.[H][C@]9(C[C@@H]%10CCN9C[C@@H]%10C=C)[C@H](O)C%11=C%12C=C(OC)C=CC%12=NC=C%11

InChI

InChIKey=CDTYBBCOIQJQRO-INGJVHGESA-N

InChI=1S/3C20H24N2O2.2AsH3O4/c3*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;2*2-1(3,4)5/h3*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*(H3,2,3,4,5)/t3*13-,14-,19-,20+;;/m000../s1

HIDE SMILES / InChI

Molecular Formula	AsH3O4
Molecular Weight	141.943
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H24N2O2
Molecular Weight	324.4168
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://link.springer.com/chapter/10.1007/978-1-4684-6168-8_3 | https://www.nj.gov/health/eoh/rtkweb/documents/fs/0086.pdf

Ammonium dihydrogen arsenate is an inorganic compound that has been considered a potential electro-optic material and has been explored by a number of investigators for modulation purposes. Ammonium arsenate is a cancerogenic substance.

Approval Year

PubMed

Title	Date	PubMed
Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms.	1998 Apr	9548797
Genetic variation in genes associated with arsenic metabolism: glutathione S-transferase omega 1-1 and purine nucleoside phosphorylase polymorphisms in European and indigenous Americans.	2003 Aug	12928150
Valproate-induced neural tube defects in folate-binding protein-2 (Folbp2) knockout mice.	2003 Dec	14745917
Human 3'-phosphoadenosine 5'-phosphosulfate synthetase (isoform 1, brain): kinetic properties of the adenosine triphosphate sulfurylase and adenosine 5'-phosphosulfate kinase domains.	2004 Apr 13	15065880
Glutathione modulates recombinant rat arsenic (+3 oxidation state) methyltransferase-catalyzed formation of trimethylarsine oxide and trimethylarsine.	2004 Dec	15606138
Arsenic induced inhibition of delta-aminolevulinate dehydratase activity in rat blood and its response to meso 2,3-dimercaptosuccinic acid and monoisoamyl DMSA.	2004 Mar	15202869
Regulation of cytoplasmic stress granules by apoptosis-inducing factor.	2004 Sep 1	15316071
Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children.	2005 Jun	15929903
Organic anion transporting polypeptide-C mediates arsenic uptake in HEK-293 cells.	2006 Jul	16479312
Arsenite-induced cytotoxicity in dorsal root ganglion explants.	2008 Apr 15	18226606
Effects of inorganic arsenic on the rat and mouse urinary bladder.	2008 Dec	18728046
High dietary fat exacerbates arsenic-induced liver fibrosis in mice.	2008 Mar	18296743
Mechanism of thiol-supported arsenate reduction mediated by phosphorolytic-arsenolytic enzymes: II. Enzymatic formation of arsenylated products susceptible for reduction to arsenite by thiols.	2009 Aug	19478237
Effects of different inorganic arsenic species in Cyprinus carpio (Cyprinidae) tissues after short-time exposure: bioaccumulation, biotransformation and biological responses.	2009 Dec	19632019
Fast, quantitative in situ hybridization of rare mRNAs using 14C-standards and phosphorus imaging.	2009 Dec 15	19761793
Inorganic arsenic modulates the expression of selenoproteins in mouse embryonic stem cell.	2009 Jun 1	19429247
Disruption of the arsenic (+3 oxidation state) methyltransferase gene in the mouse alters the phenotype for methylation of arsenic and affects distribution and retention of orally administered arsenate.	2009 Oct	19691357

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:19 GMT 2023`
Record UNII	8C15XFK30P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Quinine arsenate

Common Name

English

Cinchonan-9-ol, 6′-methoxy-, (8α,9R)-, arsenate (3:2) (salt)

Systematic Name

English

Quinine arsenate [WHO-DD]

Common Name

English

CHININUM ARSENICICUM [HPUS]

Common Name

English

CHININUM ARSENICICUM

Common Name

English

Arsenic acid (H<sub>3</sub>AsO<sub>4</sub>), compd. with (8α,9R)-6′-methoxycinchonan-9-ol (2:3)

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547