CAS 522-60-1|Ethylhydrocupreine

Introduction：Basic information about CAS 522-60-1|Ethylhydrocupreine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Ethylhydrocupreine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles25
8. Synonyms

Common Name	Ethylhydrocupreine
CAS Number	522-60-1	Molecular Weight	340.45900
Density	1.18g/cm3	Boiling Point	508.7ºC at 760mmHg
Molecular Formula	C₂₁H₂₈N₂O₂	Melting Point	123-128° when solvent-free
MSDS	ChineseUSA	Flash Point	261.5ºC
Symbol	GHS07	Signal Word	Warning

Names

Name	optochin
Synonym	More Synonyms

Ethylhydrocupreine BiologicalActivity

Description	Ethylhydrocupreine (Optochin) is a quinine derivate with antimicrobial activity against S. pneumoniae. Ethylhydrocupreine also possesses antimalarial activity against Plasmodium falciparum, with an IC50 of 25.75 nM. Ethylhydrocupreine is a Gallus gallus taste 2 receptors (ggTas2r1, ggTas2r2 and ggTas2r7) agonist[1][2][3][4].
Related Catalog	Research Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial
Target	S. pneumoniae[1] IC50: 25.75 nM (Plasmodium falciparum)[3] ggTas2r1, ggTas2r2 and ggTas2r7[4]
In Vitro	The mutation rate to Ethylhydrocupreine (Optochin) resistance is estimated using fluctuation analysis in three capsulated S. pneumoniae strains (S. pneumoniae D39 NCTC 7466, S. pneumoniae R6 ATCC BAA-255 and S. pneumoniae ATCC 49619). The exposure to subinhibitory concentrations of penicillin increased the mutation rate (expressed as mutation per cell division) to Ethylhydrocupreine (Optochin) resistance between 2.1- and 3.1-fold for all three strains studied[2].
In Vivo	The injection of 1 cc. of a 24 hour dextrose blood broth culture of virulent Type I pneumococci into the right pleural cavity of guinea pigs produces acute suppurative pleuritis on both sides associated with suppurative pericarditis. The injection of 1 cc. of 1:500 solutions of Ethylhydrocupreine hydrochloride into each pleural cavity of guinea pigs at varying intervals up to 24 hours after pleural infection has usually shown a marked curative influence. Similar results are observed with dogs[1].
References	[1]. J A Kolmer, et al. CHEMOTHERAPEUTIC STUDIES WITH ETHYLHYDROCUPREINE HYDROCHLORIDE IN EXPERIMENTAL PNEUMOCOCCUS PLEURITIS. J Exp Med. 1921 May 31;33(6):693-711. [2]. Paulo R Cortes, et al. Subinhibitory Concentrations of Penicillin Increase the Mutation Rate to Optochin Resistance in Streptococcus Pneumoniae. J Antimicrob Chemother. 2008 Nov;62(5):973-7. [3]. Nassira Mahmoudi, et al. Identification of New Antimalarial Drugs by Linear Discriminant Analysis and Topological Virtual Screening. J Antimicrob Chemother. 2006 Mar;57(3):489-97. [4]. Antonella Di Pizio, et al. Molecular Features Underlying Selectivity in Chicken Bitter Taste Receptors. Front Mol Biosci. 2018 Jan 31;5:6.

Chemical & Physical Properties

Density	1.18g/cm3
Boiling Point	508.7ºC at 760mmHg
Melting Point	123-128° when solvent-free
Molecular Formula	C₂₁H₂₈N₂O₂
Molecular Weight	340.45900
Flash Point	261.5ºC
Exact Mass	340.21500
PSA	45.59000
LogP	3.72520
Index of Refraction	1.618
InChIKey	SUWZHLCNFQWNPE-LATRNWQMSA-N
SMILES	CCOc1ccc2nccc(C(O)C3CC4CCN3CC4CC)c2c1
Storage condition	2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MW5950000

CHEMICAL NAME :: Hydrocupreine, O(sup 6')-ethyl-

CAS REGISTRY NUMBER :: 522-60-1

BEILSTEIN REFERENCE NO. :: 0092227

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C21-H28-N2-O2

MOLECULAR WEIGHT :: 340.51

WISWESSER LINE NOTATION :: T66 BNJ HO2 EYQ- DT66 A B CNTJ G2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

REFERENCE :: OPHTAD Ophtalmologica. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.96- 1978- Volume(issue)/page/year: 143,154,1962 ** ACUTE TOXICITY DATA **

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 24 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1289,1935

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn
Risk Phrases	22
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	MW5950000
HS Code	2933990090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles25

Identifying mutator phenotypes among fluoroquinolone-resistant strains of Streptococcus pneumoniae using fluctuation analysis.

Antimicrob. Agents Chemother. 51 , 3225-9, (2007)

The occurrence of mutator phenotypes among laboratory-generated and clinical levofloxacin-resistant strains of Streptococcus pneumoniae was determined using fluctuation analysis. The in vitro selectio...

Genotypic identification of presumptive Streptococcus pneumoniae by PCR using four genes highly specific for S. pneumoniae.

J. Med. Microbiol. 55(Pt 6) , 709-14, (2006)

It was previously reported that two oligonucleotide primer sets (spn9802 and spn9828) for discriminating Streptococcus pneumoniae from pneumococcus-like oral streptococcal isolates using PCR had been ...

Possible overestimation of penicillin resistant Streptococcus pneumoniae colonization rates due to misidentification of oropharyngeal streptococci.

Diagn. Microbiol. Infect. Dis. 42(4) , 263-8, (2002)

Standard identification of Streptococcus pneumoniae by optochin and bile solubility testing can lead to ambiguous results for certain isolates. Newer bacteriologic identification techniques (e.g., DNA...

Synonyms

Optochine

hydrocupreineethylether

ETHYLHYDROCUPREINE

Hydrocupureine ethyl ether

Numoquine

Ethylhydrocuprein

numoquin

optoquine

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