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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22NO3.Cl
Molecular Weight 335.825
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MORPHINE METHYLCHLORIDE

SMILES

[Cl-].[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=MJNCZWBHCFTYFU-SCLAZZCHSA-N
InChI=1S/C18H21NO3.ClH/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;1H/t11-,12+,14-,17-,18-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C18H21NO3
Molecular Weight 299.3642
Charge 0
Count
Stereochemistry EPIMERIC
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

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

4.64313614E11
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
Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine).
1999 Aug 25
Preliminary UK experience of dexmedetomidine, a novel agent for postoperative sedation in the intensive care unit.
1999 Dec
Seizure and electroencephalographic changes in the newborn period induced by opiates and corrected by naloxone infusion.
1999 Mar
Sleep impairments in rats implanted with morphine pellets.
1999 Nov
Morphine promotes apoptosis in Jurkat cells.
1999 Oct
Rhabdomyolysis-induced acute renal failure after morphine overdose--a case report.
1999 Sep
Morphine inhibits human microglial cell production of, and migration towards, RANTES.
2000
Peroperative titration of morphine improves immediate postoperative analgesia after total hip arthroplasty.
2000 Apr
Intrathecal morphine suppresses NK cell activity following abdominal surgery.
2000 Apr
The effects of intrathecal morphine encapsulated in L- and D-dipalmitoylphosphatidyl choline liposomes on acute nociception in rats.
2000 Aug
Apnoea with intrathecal morphine.
2000 Dec
The development of pain-related behaviour and opioid tolerance after neuropathy-inducing surgery and sham surgery.
2000 Dec 1
Preemptive intravenous morphine-6-glucuronide is ineffective for postoperative pain relief.
2000 Feb
Reversal of morphine-induced apnea in the anesthetized rat by drugs that activate 5-hydroxytryptamine(1A) receptors.
2000 Feb
Previous cholecystectomy and choledochal sphincter spasm after morphine sedation.
2000 Jan
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
Pethidine reverses morphine-induced delirium.
2000 Jun
Effects of the NMDA receptor channel blockers memantine and MRZ 2/579 on morphine withdrawal-facilitated aggression in mice.
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
Downbeat nystagmus associated with intravenous patient-controlled administration of morphine.
2000 Sep
Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects.
2000 Sep
mGlu5 receptors and nociceptive function II. mGlu5 receptors functionally expressed on peripheral sensory neurones mediate inflammatory hyperalgesia.
2001
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor.
2001 Apr
Large-dose oral dextromethorphan as an adjunct to patient-controlled analgesia with morphine after knee surgery.
2001 Feb
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection.
2001 Feb
A single nucleotide polymorphic mutation in the human mu-opioid receptor severely impairs receptor signaling.
2001 Feb 2
Multicentre randomised controlled trial of nasal diamorphine for analgesia in children and teenagers with clinical fractures.
2001 Feb 3
Knockdown of spinal metabotropic glutamate receptor 1 (mGluR(1)) alleviates pain and restores opioid efficacy after nerve injury in rats.
2001 Jan
Circuitry underlying antiopioid actions of cholecystokinin within the rostral ventromedial medulla.
2001 Jan
Ketorolac reduces postoperative narcotic requirements.
2001 Jan
Prehospital management of rapid atrial fibrillation: recommendations for treatment protocols.
2001 Jan
Early serial EEG in hypoxic ischaemic encephalopathy.
2001 Jan
Randomized clinical trial of diathermy versus scalpel incision in elective midline laparotomy.
2001 Jan
Opiates, intracranial pressure, and autoregulation.
2001 Jan
Buprenorphine substitution ameliorates spontaneous withdrawal in fentanyl-dependent rat pups.
2001 Jan
A prospective survey of patients after cessation of patient-controlled analgesia.
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
A randomized, double-blinded comparison of intrathecal morphine, sufentanil and their combination versus IV morphine patient-controlled analgesia for postthoracotomy pain.
2001 Jan
Agmatine enhances the NADPH oxidase activity of neuronal NO synthase and leads to oxidative inactivation of the enzyme.
2001 Jan
Parental perceptions of comfort during mechanical ventilation.
2001 Jan
Sublingual morphine may be a suitable alternative for pain control in children in the postoperative period.
2001 Jan
Augmented accumbal serotonin levels decrease the preference for a morphine associated environment during withdrawal.
2001 Jan
Heroin-related deaths in Victoria: a review of cases for 1997 and 1998.
2001 Jan 1
Numerical density of mu opioid receptor expressing neurons in the frontal cortex of drug related fatalities.
2001 Jan 15
Acute thermal hyperalgesia elicited by low-dose morphine in normal mice is blocked by ultra-low-dose naltrexone, unmasking potent opioid analgesia.
2001 Jan 5
Occurrence of morphine tolerance and dependence in the nucleus paragigantocellularis neurons.
2001 Jan 5
Morphine induces short-lived changes in G-protein gene expression in rat prefrontal cortex.
2001 Jan 5
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 01:57:16 UTC 2023
Edited
by admin
on Sat Dec 16 01:57:16 UTC 2023
Record UNII
D74B54D2RE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MORPHINE METHYLCHLORIDE
Common Name English
MORPHINANIUM, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-3,6.ALPHA.-DIHYDROXY-17,17-DIMETHYL-, CHLORIDE
Systematic Name English
MORPHINANIUM, 7,8-DIDEHYDRO-4,5-EPOXY-3,6-DIHYDROXY-17,17-DIMETHYL-, CHLORIDE (1:1), (5.ALPHA.,6.ALPHA.)-
Systematic Name English
N-METHYLMORPHINE CHLORIDE
Common Name English
(4R,4AR,7S,7AR,12BS)-3,3-DIMETHYL-2,4,4A,7,7A,13-HEXAHYDRO-1H-4,12-METHANOBENZOFURO(3,2-E)ISOQUINOLINE-3-IUM-7,9-DIOL CHLORIDE
Systematic Name English
5.7,8-DIDEHYDRO-4,5-EPOXY-3,6-DIHYDROXY-17,17-DIMETHYLMORPHINANIUM CHLORIDE, (5ALPHA,6ALPHA)-
Systematic Name English
(5.ALPHA.,6.ALPHA.)-3,6-DIHYDROXY-17,17-DIMETHYL-7,8-DIDEHYDRO-4,5-EPOXYMORPHINAN-17-IUM CHLORIDE
Systematic Name English
N-METHYLMORPHINIUM CHLORIDE
Common Name English
Code System Code Type Description
PUBCHEM
5492950
Created by admin on Sat Dec 16 01:57:16 UTC 2023 , Edited by admin on Sat Dec 16 01:57:16 UTC 2023
PRIMARY
FDA UNII
D74B54D2RE
Created by admin on Sat Dec 16 01:57:16 UTC 2023 , Edited by admin on Sat Dec 16 01:57:16 UTC 2023
PRIMARY
EPA CompTox
DTXSID60930915
Created by admin on Sat Dec 16 01:57:16 UTC 2023 , Edited by admin on Sat Dec 16 01:57:16 UTC 2023
PRIMARY
CAS
14075-02-6
Created by admin on Sat Dec 16 01:57:16 UTC 2023 , Edited by admin on Sat Dec 16 01:57:16 UTC 2023
PRIMARY
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