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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO3.ClH.2H2O
Molecular Weight 385.882
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE

SMILES

O.O.Cl.[H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3OCC

InChI

InChIKey=FKEDUFRSQFFLHR-VSYPDCRNSA-N
InChI=1S/C19H23NO3.ClH.2H2O/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18;;;/h4-7,12-14,18,21H,3,8-10H2,1-2H3;1H;2*1H2/t12-,13+,14-,18-,19-;;;/m0.../s1

HIDE SMILES / InChI
Molecular Formula C19H23NO3
Molecular Weight 313.3908
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Ethylmorphine is a derivative of morphine with analgesic and antitussive effect. It acts by activating the opioid receptors and thus has a direct influence on the CNS system. Ethylmorphine was approved in Europe for the treatment of dry cough (Codethyline, Dionine).

CNS Activity

Approval Year

1921
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 345.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
CODETHYLINE

Approved Use

A cough medicine.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.09 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7654478
1.5 mg/kg bw single, oral
dose: 1.5 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLMORPHINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
222 μM × min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7654478
1.5 mg/kg bw single, oral
dose: 1.5 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLMORPHINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.97 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7654478
1.5 mg/kg bw single, oral
dose: 1.5 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
ETHYLMORPHINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
8.5 mg single, oral
Dose: 8.5 mg
Route: oral
Route: single
Dose: 8.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/20158595
healthy, 10 months
n = 1
Health Status: healthy
Age Group: 10 months
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/20158595
Other AEs: Sedation...
Other AEs:
Sedation (grade 5)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20158595
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
Other AEs: Dizziness, Drowsiness...
Other AEs:
Dizziness (7 patients)
Drowsiness (slight, 2 patients)
Loose stools (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
AEs

AEs

AESignificanceDosePopulation
Sedation grade 5
8.5 mg single, oral
Dose: 8.5 mg
Route: oral
Route: single
Dose: 8.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/20158595
healthy, 10 months
n = 1
Health Status: healthy
Age Group: 10 months
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/20158595
Loose stools 1 patient
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
Dizziness 7 patients
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
Drowsiness slight, 2 patients
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/7654478
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1217
 yes
CYP3A4
1737
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1Q37UW
Ambinter
Amb22801513
http://www.ambinter.com/reference/22801513
Angene
AGN-PC-0OHUE6
Aurora Fine Chemicals LLC
A17.879.672
http://online.aurorafinechemicals.com/info?ID=A17.879.672
ChemMol
99147254
http://www.chemmol.com/chemmol/99147254.html
Chemieliva Pharmaceutical Co., Ltd
PBCM1411510
Compound Cloud
23724836
Compound Cloud
5359271
Debye Scientific
DB-056088
Glentham Life Sciences
GP3600
http://www.glentham.com/products/product/GP3600/
LGC Standards
LGCAMP0799.07-01
https://www.lgcstandards.com/US/en/p/LGCAMP0799.07-01
LGC Standards
LGCFOR0799.07
https://www.lgcstandards.com/US/en/p/LGCFOR0799.07
LGC Standards
MM0799.07
https://www.lgcstandards.com/US/en/p/MM0799.07
NovoSeek
5359271
Sigma Aldrich
E-052
Sigma Aldrich
E8512
Sigma Aldrich
E8512|SIGMA
Sigma-Aldrich
E-052_CERILLIAN
https://www.sigmaaldrich.com/catalog/product/cerillian/e052?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich
E8512_SIGMA
https://www.sigmaaldrich.com/catalog/product/sigma/e8512?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S620625
https://www.smolecule.com/products/s620625
Tetrahedron
TS61083
ZINC
ZINC000003629718
http://zinc15.docking.org/substances/ZINC000003629718
eMolecules
193735204
PubMed

PubMed

TitleDatePubMed
Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose.
1995 Jun
Effects of ethanol on ethylmorphine metabolism in isolated rat hepatocytes: characterization by means of a multicompartmental model.
1997 Apr
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.
2001 Aug
Effects of fumonisin B1 present in Fusarium moniliforme culture material on drug metabolising enzyme activities in ducks.
2001 May 19
Genomic characterization and regulation of CYP3a13: role of xenobiotics and nuclear receptors.
2003 Sep
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004 Jul 16
Biochemical background of toxic interaction between tiamulin and monensin.
2004 Mar 15
Automated multiple development thin-layer chromatography for separation of opiate alkaloids and derivatives.
2005 Jul 8
Validation of direct injection electrospray LC-MS/MS for confirmation of opiates in urine drug testing.
2007 Jul
A hybrid FIA/HPLC system incorporating monolithic column chromatography.
2007 Sep 26
[Study of cytotoxic and antiviral effects of some eye drops].
2008
Error in the article: "driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood".
2008 Jun
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.
2008 May
[Pharmacological treatment of acute cough].
2009 May 14
Effect of cytisine on some brain and hepatic biochemical parameters in spontaneously hypertensive rats.
2010 Mar
Patents

Patents

JP2000516204A
66
JP2001058957A
4
JP2002541233A
400
JP2003515526A
462
JP2011513278A
28
JPH00286794A
24
JPH0286794A
7

Sample Use Guides

In Vivo Use Guide
The recommended dose in adults is 50 mg of codethyline per day, i.e. 10 tablets (1 tablet contains 5 mg of ethylmorphine hydrochloride) per day over several intakes, at a minimum of 4 hours apart. In children the normal dose is 1 tablet per intake, to be renewed after 6 hours if necessary, without exceeding 4 tablets per day.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:26:53 GMT 2023
Edited
by admin
on Fri Dec 15 17:26:53 GMT 2023
Record UNII
407X3NQV4N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE
MI   WHO-DD  
Common Name English
ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE [MI]
Common Name English
ETHYLMORPHINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-ETHOXY-17-METHYLMORPHINAN-6-OL HYDROCHLORIDE DIHYDRATE
Systematic Name English
CODETHYLINE HYDROCHLORIDE DIHYDRATE
Common Name English
ETHYLMORPHINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
Ethylmorphine hydrochloride dihydrate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
Code System Code Type Description
MERCK INDEX
m5154
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C87358
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID90986728
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
SMS_ID
300000037439
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
FDA UNII
407X3NQV4N
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
PUBCHEM
5360215
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
CAS
6746-59-4
Created by admin on Fri Dec 15 17:26:53 GMT 2023 , Edited by admin on Fri Dec 15 17:26:53 GMT 2023
PRIMARY
Related Record Type Details
Structure of ETHYLMORPHINE HYDROCHLORIDE
ANHYDROUS->SOLVATE
Structure of ETHYLMORPHINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of MORPHINE
IMPURITY -> PARENT
Structure of CODEINE ANHYDROUS
IMPURITY -> PARENT
Structure of Ethylmorphinone
IMPURITY -> PARENT
Structure of 7,8-didehydro-4,5α-epoxy-3,6α-diethoxy-17-methylmorphinan
IMPURITY -> PARENT
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