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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22NO3
Molecular Weight 300.3722
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of N-METHYLMORPHINE ION

SMILES

[H][C@]12OC3=C4C(C[C@]5([H])[C@]([H])(C=C[C@@H]1O)[C@]24CC[N+]5(C)C)=CC=C3O

InChI

InChIKey=UJSDOZFJXZOOGN-XSSYPUMDSA-O
InChI=1S/C18H21NO3/c1-19(2)8-7-18-11-4-6-14(21)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,11-12,14,17,21H,7-9H2,1-2H3/p+1/t11-,12+,14-,17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H22NO3
Molecular Weight 300.3722
Charge 1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Morphine is one of the most important and widely used opioid for the treatment of chronic and acute pain: the very wide interindividual variability in the patients’ response to the drug may have genetic derivations. Sulphate salt of morphine sold under the many brand names, one of them, DURAMORPH, which is indicated for the management of pain severe enough to require use of an opioid analgesic by intravenous administration, and for which alternative treatments are not expected to be adequate. In addition for the epidural or intrathecal management of pain without attendant loss of motor, sensory, or sympathetic function. Morphine is a full opioid agonist and is relatively selective for the mu-opioid receptor, although it can bind to other opioid receptors at higher doses. The principal therapeutic action of morphine is analgesia. Like all full opioid agonists, there is no ceiling effect for analgesia with morphine. The precise mechanism of the analgesic action is unknown. However, specific CNS opioid receptors for endogenous compounds with opioid-like activity have been identified throughout the brain and spinal cord and are thought to play a role in the analgesic effects of this drug. Morphine has a high potential for addiction and abuse. Common side effects include drowsiness, vomiting, and constipation. Caution is advised when used during pregnancy or breast-feeding, as morphine will affect the baby.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
Target ID: P41143
Gene ID: 4985.0
Gene Symbol: OPRD1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DURAMORPH PF

Approved Use

DURAMORPH is indicated for: the management of pain severe enough to require use of an opioid analgesic by intravenous administration, and for which alternative treatments are not expected to be adequate.For the epidural or intrathecal management of pain without attendant loss of motor, sensory, or sympathetic function.

Launch Date

1984
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
63 nM
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
165 nM × h
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.1 h
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
65%
2 mg single, intravenous
dose: 2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MORPHINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
healthy, adult
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
180 mg 1 times / day steady, oral
Dose: 180 mg, 1 times / day
Route: oral
Route: steady
Dose: 180 mg, 1 times / day
Sources:
unhealthy, adult
n = 152
Health Status: unhealthy
Condition: neuropathic pain
Age Group: adult
Sex: unknown
Population Size: 152
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
yes [Km 10100 uM]
yes [Km 12600 uM]
yes [Km 14150 uM]
yes [Km 18000 uM]
yes [Km 18700 uM]
yes [Km 25400 uM]
yes [Km 2600 uM]
yes [Km 3.4 uM]
yes [Km 3200 uM]
yes [Km 37400 uM]
yes [Km 380 uM]
yes [Km 4800 uM]
yes [Km 6400 uM]
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs.
1976 Aug
Psychopharmacological studies on (--)-nuciferine and its Hofmann degradation product atherosperminine.
1978 Sep 15
Morphine preconditioning attenuates neutrophil activation in rat models of myocardial infarction.
1998 Dec
The effects of dopamine D2 and D3 antagonists on spontaneous motor activity and morphine-induced hyperactivity in male mice.
1999 Mar
The effects of quinine and 4-aminopyridine on conditioned place preference and changes in motor activity induced by morphine in rats.
1999 May
Controlling myoclonus after high-dosage morphine infusions.
1999 May 15
Morphine promotes apoptosis in Jurkat cells.
1999 Oct
Effects of SCH 23390, raclopride, and haloperidol on morphine withdrawal-induced aggression in male mice.
1999 Sep
Effects of morphine and tramadol on somatic and visceral sensory function and gastrointestinal motility after abdominal surgery.
1999 Sep
Potentiation of narcosis after intravenous lidocaine in a patient given spinal opioids.
1999 Sep
Morphine induced allodynia in a child with brain tumour.
1999 Sep 4
The effect of spinal ibuprofen on opioid withdrawal in the rat.
2000 Aug
Apnoea with intrathecal morphine.
2000 Dec
Prenatal morphine exposure alters N-methyl-D-aspartate- and kainate-induced seizures in adult male rats.
2000 Jan 1
Orphanin FQ/nociceptin inhibits morphine withdrawal.
2000 Jan 14
Cyclophosphamide-induced cystitis in freely-moving conscious rats: behavioral approach to a new model of visceral pain.
2000 Jul
Pethidine reverses morphine-induced delirium.
2000 Jun
Lack of specific effects of selective D(1) and D(2) dopamine antagonists vs. risperidone on morphine-induced hyperactivity.
2000 May
Insidious intoxication after morphine treatment in renal failure: delayed onset of morphine-6-glucuronide action.
2000 May
Systemic naloxone enhances cerebral blood flow in anesthetized morphine-dependent rats.
2000 Nov 24
Enhanced spinal nociceptin receptor expression develops morphine tolerance and dependence.
2000 Oct 15
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection.
2001 Feb
Ketorolac reduces postoperative narcotic requirements.
2001 Jan
Opiates, intracranial pressure, and autoregulation.
2001 Jan
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes.
2001 Jan
Bupivacaine wound instillation via an electronic patient-controlled analgesia device and a double-catheter system does not decrease postoperative pain or opioid requirements after major abdominal surgery.
2001 Jan
Agmatine enhances the NADPH oxidase activity of neuronal NO synthase and leads to oxidative inactivation of the enzyme.
2001 Jan
Numerical density of mu opioid receptor expressing neurons in the frontal cortex of drug related fatalities.
2001 Jan 15
Effect of organic cations on the renal tubular secretion of pseudoephedrine in the rat.
2001 Jan-Feb
Patents

Sample Use Guides

Dosage for Intravenous Administration: Adult Dosage: The initial dose of morphine should be 2 mg to 10 mg/70 kg of body weight. Dosage for Epidural Administration: Adult Dosage: Initial injection of 5 mg in the lumbar region may provide satisfactory pain relief for up to 24 hours. If adequate pain relief is not achieved within one hour, careful administration of incremental doses of 1 to 2 mg at intervals sufficient to assess effectiveness may be given. Do not administer more than 10 mg per 24 hours. Dosage for Intrathecal Administration: Adult Dosage: Intrathecal dosage is usually 1/10 that of epidural dosage. A single injection of 0.2 to 1 mg may provide satisfactory pain relief for up to 24 hours. (Caution: this is only 0.4 to 2 mL of the 5 mg/10 mL ampul or 0.2 to 1 mL of the 10 mg/10 mL ampul of DURAMORPH). Do not inject intrathecally more than 2 mL of the 5 mg/10 mL ampul or 1 mL of the 10 mg/10 mLampul. Repeated intrathecal injections of DURAMORPH are not recommended. If pain recurs, consider consider alternative routes of administration.
Route of Administration: Other
It was evaluated the effect of morphine on the proangiogenic interaction taking place between macrophages and breast cancer cells in vitro. It was shown, that morphine prevents, in part via modulating VEGF-A expression, the pro-angiogenic interaction between macrophages and breast cancer cells. The conditioned medium (CM) from breast cancer cells co-cultured with macrophages elicited endothelial cell proliferation and tube formation. This effect was inhibited if the co-culture occurred in the presence of morphine (20 uM). Using a mouse antibody array, it was identified several angiogenesis-regulating factors differentially expressed in the CM of co-cultured cells prepared in the presence or absence of morphine (o, 10, 20 uM), amongst which interleukin (IL)-6, tumour necrosis factor (TNF)-α and vascular endothelial growth factor (VEGF)-A. VEGF was induced in both cell types by the co-culture and this was prevented by morphine in a non-naloxone reversible fashion. The effect of CM from co-cultured cells on endothelial tube formation, but not proliferation, was prevented by anti-VEGF neutralizing antibody
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:38:40 GMT 2023
Edited
by admin
on Sat Dec 16 15:38:40 GMT 2023
Record UNII
HNJ4VEK3VI
Record Status Validated (UNII)
Record Version
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Name Type Language
N-METHYLMORPHINE ION
Common Name English
MORPHINANIUM, 7,8-DIDEHYDRO-4,5-EPOXY-3,6-DIHYDROXY-17,17-DIMETHYL-, (5.ALPHA.,6.ALPHA.)-
Systematic Name English
(5.ALPHA.,6.ALPHA.)-7,8-DIDEHYDRO-4,5-EPOXY-3,6-DIHYDROXY-17,17-DIMETHYLMORPHINANIUM
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID10161797
Created by admin on Sat Dec 16 15:38:40 GMT 2023 , Edited by admin on Sat Dec 16 15:38:40 GMT 2023
PRIMARY
CAS
14168-11-7
Created by admin on Sat Dec 16 15:38:40 GMT 2023 , Edited by admin on Sat Dec 16 15:38:40 GMT 2023
PRIMARY
PUBCHEM
5362446
Created by admin on Sat Dec 16 15:38:40 GMT 2023 , Edited by admin on Sat Dec 16 15:38:40 GMT 2023
PRIMARY
FDA UNII
HNJ4VEK3VI
Created by admin on Sat Dec 16 15:38:40 GMT 2023 , Edited by admin on Sat Dec 16 15:38:40 GMT 2023
PRIMARY
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