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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H23NO3
Molecular Weight 313.3915
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLMORPHINE

SMILES

CCOc1ccc2C[C@]3([H])[C@]4([H])C=C[C@@]([H])([C@@]5([H])[C@]4(CCN3C)c2c1O5)O

InChI

InChIKey=OGDVEMNWJVYAJL-LEPYJNQMSA-N
InChI=1S/C19H23NO3/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/t12-,13+,14-,18-,19-/m0/s1

HIDE SMILES / InChI
Molecular Formula C19H23NO3
Molecular Weight 313.3915
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
1413
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2470
 345.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
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
1601
substrate
1118

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1118
 yes
CYP3A4
1601
 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
Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.
2001 Aug
Screening for drugs of abuse in hair with ion spray LC-MS-MS.
2004 Oct 29
Inhibition of rat liver CYP2D in vitro and after 1-day and long-term exposure to neuroleptics in vivo-possible involvement of different mechanisms.
2005 Jan
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
Purification of CYP2B-like protein from feral leaping mullet (Liza saliens) liver microsomes and its biocatalytic, molecular, and immunological characterization.
2008 Jul-Aug
Determining plasma morphine levels using GC-MS after solid phase extraction to monitor drug levels in the postoperative period.
2008 Jun
Driving under the influence of opiates: concentration relationships between morphine, codeine, 6-acetyl morphine, and ethyl morphine in blood.
2008 May
Simultaneous screening and quantification of 25 opioid drugs in post-mortem blood and urine by liquid chromatography-tandem mass spectrometry.
2009 Apr 15
Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS.
2009 Feb 1
[Pharmacological treatment of acute cough].
2009 May 14
Effect of cytisine on some brain and hepatic biochemical parameters in spontaneously hypertensive rats.
2010 Mar
Bovine liver slices combined with an androgen transcriptional activation assay: an in-vitro model to study the metabolism and bioactivity of steroids.
2010 May
Patents

Patents

JP2000516204A
63
JP2001058957A
3
JP2002541233A
371
JP2003515526A
430
JP2011513278A
27
JPH00286794A
17
JPH0286794A
6

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 Sat Jun 26 06:45:46 UTC 2021
Edited
by admin
on Sat Jun 26 06:45:46 UTC 2021
Record UNII
RWO67D87EU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYLMORPHINE
MI   WHO-DD  
Common Name English
IDS-NE-005(SECT.2)
Code English
R05DA01
Code English
CODETHYLINE
Common Name English
ETHYLMORPHINE [WHO-DD]
Common Name English
3-ETHOXYMORPHINE
Common Name English
ETHYLMORPHINE [MI]
Common Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3-ETHOXY-17-METHYLMORPHINAN-6-OL
Systematic Name English
Classification Tree Code System Code
WHO-VATC QS01XA06
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
DEA NO. 9190
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
NCI_THESAURUS C67413
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
WHO-ATC S01XA06
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
WHO-VATC QR05DA01
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
WHO-ATC R05DA01
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
Code System Code Type Description
DRUG CENTRAL
3207
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
MESH
D005036
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
RXCUI
4166
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY RxNorm
PUBCHEM
5359271
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-970-7
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
DRUG BANK
DB01466
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
FDA UNII
RWO67D87EU
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
EPA CompTox
76-58-4
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
ChEMBL
CHEMBL1712170
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
WIKIPEDIA
ETHYLMORPHINE
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
CAS
76-58-4
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
NCI_THESAURUS
C83704
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
MERCK INDEX
M5154
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY Merck Index
EVMPD
SUB13765MIG
Created by admin on Sat Jun 26 06:45:46 UTC 2021 , Edited by admin on Sat Jun 26 06:45:46 UTC 2021
PRIMARY
Related Record Type Details
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
Structure of ETHYLMORPHINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Structure of ETHYLMORPHINE HYDROCHLORIDE DIHYDRATE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
Structure of ETHYLMORPHINE
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