U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
345.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CODETHYLINE

Approved Use

A cough medicine.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.09 μM
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
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
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:
healthy, 10 months
n = 1
Health Status: healthy
Age Group: 10 months
Sex: M
Population Size: 1
Sources:
Other AEs: Sedation...
Other AEs:
Sedation (grade 5)
Sources:
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Other AEs: Dizziness, Drowsiness...
Other AEs:
Dizziness (7 patients)
Drowsiness (slight, 2 patients)
Loose stools (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Sedation grade 5
8.5 mg single, oral
Dose: 8.5 mg
Route: oral
Route: single
Dose: 8.5 mg
Sources:
healthy, 10 months
n = 1
Health Status: healthy
Age Group: 10 months
Sex: M
Population Size: 1
Sources:
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:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Dizziness 7 patients
1.5 mg/kg single, oral
Dose: 1.5 mg/kg
Route: oral
Route: single
Dose: 1.5 mg/kg
Sources:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
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:
healthy, 24 years
n = 10
Health Status: healthy
Age Group: 24 years
Sex: M
Population Size: 10
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim
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

Sample Use Guides

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
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
ACTIVE MOIETY