Ethylhydrocupreine hydrochloride

Modify Date: 2025-08-21 23:22:21

Ethylhydrocupreine hydrochloride Structure
Ethylhydrocupreine hydrochloride structure
Common Name Ethylhydrocupreine hydrochloride
CAS Number 3413-58-9 Molecular Weight 376.92000
Density N/A Boiling Point 508.7ºC at 760 mmHg
Molecular Formula C21H29ClN2O2 Melting Point 121-123ºC
MSDS USA Flash Point 261.5ºC

 Use of Ethylhydrocupreine hydrochloride


Ethylhydrocupreine hydrochloride (Optochin hydrochloride) is a quinine derivate with antimicrobial activity against S. pneumoniae. Ethylhydrocupreine hydrochloride also possesses antimalarial activity against Plasmodium falciparum, with an IC50 of 25.75 nM. Ethylhydrocupreine hydrochloride is a Gallus gallus taste 2 receptors (ggTas2r1, ggTas2r2 and ggTas2r7) agonist[1][2][3][4].

 Names

Name ethylhydrocupreine hydrochloride
Synonym More Synonyms

 Ethylhydrocupreine hydrochloride Biological Activity

Description Ethylhydrocupreine hydrochloride (Optochin hydrochloride) is a quinine derivate with antimicrobial activity against S. pneumoniae. Ethylhydrocupreine hydrochloride also possesses antimalarial activity against Plasmodium falciparum, with an IC50 of 25.75 nM. Ethylhydrocupreine hydrochloride is a Gallus gallus taste 2 receptors (ggTas2r1, ggTas2r2 and ggTas2r7) agonist[1][2][3][4].
Related Catalog
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

Boiling Point 508.7ºC at 760 mmHg
Melting Point 121-123ºC
Molecular Formula C21H29ClN2O2
Molecular Weight 376.92000
Flash Point 261.5ºC
Exact Mass 376.19200
PSA 45.59000
LogP 4.52720
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MW6300000
CHEMICAL NAME :
Hydrocupreine, O-ethyl-, hydrochloride
CAS REGISTRY NUMBER :
3413-58-9
LAST UPDATED :
199504
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C21-H28-N2-O2.Cl-H
MOLECULAR WEIGHT :
376.97
WISWESSER LINE NOTATION :
T66 BNJ HO2 EYQ- DT66 A B CNTJ G2 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
31 mg/kg/3D
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - visual field changes Vascular - regional or general arteriolar constriction
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 8,53,1916
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 8,53,1916
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 8,53,1916 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5575 No. of Facilities: 90 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 557 (estimated) No. of Female Employees: 502 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases 36/37/38
Safety Phrases S22;S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS MW6300000
HS Code 29392900

 Articles25

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 Synonyms

numoquinhydrochloride
OPTICHIN HYDROCHLORIDE
Aethyl-hydrocuprein-hydrochlorid
MFCD00135594
EINECS 222-302-3
neumolisina
o-ethyl-hydrocupreinhydrochloride
hydrocupreine,ethylester,hydrochloride
OptochineHCl
optoquinhydrochloride
optochinhydrochloride
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