Morphine

Base Information Edit

Chemical Name:Morphine
CAS No.:57-27-2
Deprecated CAS:8053-16-5,85201-37-2,47106-99-0,863713-90-0,1325730-46-8
Molecular Formula:C17H19NO3
Molecular Weight:285.343
Hs Code.:2939110014
European Community (EC) Number:200-320-2
UNII:76I7G6D29C
DSSTox Substance ID:DTXSID9023336
Nikkaji Number:J2.323J
Wikipedia:Morphine
Wikidata:Q81225
NCI Thesaurus Code:C62051
RXCUI:7052
Pharos Ligand ID:JLA4ZYGWHFQS
Metabolomics Workbench ID:42684
ChEMBL ID:CHEMBL70
Mol file:57-27-2.mol

Synonyms:Chloride, Morphine;Contin, MS;Duramorph;Morphia;Morphine;Morphine Chloride;Morphine Sulfate;Morphine Sulfate (2:1), Anhydrous;Morphine Sulfate (2:1), Pentahydrate;MS Contin;Oramorph SR;SDZ 202 250;SDZ 202-250;SDZ 202250;SDZ202 250;SDZ202-250;SDZ202250;Sulfate, Morphine

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Chemical Property of Morphine Edit

Chemical Property:

Vapor Pressure:7.06E-10mmHg at 25°C
Melting Point:255°C
Refractive Index:1.719
Boiling Point:476.247 °C at 760 mmHg
PKA:8.21(at 25℃)
Flash Point:241.826 °C
PSA：52.93000
Density:1.44 g/cm³
LogP:1.13600
Storage Temp.:−20°C
Water Solubility.:0.4mg/L(25 oC)
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:0
Exact Mass:285.13649347
Heavy Atom Count:21
Complexity:494

Purity/Quality:

Safty Information:

Pictogram(s): F,T+
Hazard Codes:F,T
Statements: 11-23/24/25-39/23/24/25
Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Chemical Classes:Biological Agents -> Plant Toxins
Drug Classes:Opioids
Canonical SMILES:CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)O
Isomeric SMILES:CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)O)O[C@H]3[C@H](C=C4)O
Recent ClinicalTrials:Morphine IV vs Paracetamol IV in Neonates and Infants After Cardiac Surgery
Recent EU Clinical Trials:Multicentre, randomized, open-label study to prove an additional
Recent NIPH Clinical Trials:The therapeutic effect of an intrathecal opioid after lumbar interbody fusion surgery
Description Morphine is the principal alkaloid obtained from opium. Opium is the resinous latex that exudes from the seed pod of the opium poppy, Papver somneferum, when it is lacerated. Alkaloids account for approximately 25% of opium, and of this 25% about 60% is morphine.
Physical properties Appearance: white or almost white crystalline powder or colorless, silky needles or cubical masses, efflorescent in a dry atmosphere. Solubility: soluble in water, slightly soluble in ethanol, practically insoluble in chloroform or ether. Specific optical rotation: ?110.0° to 115.0°
Uses A degradation product of Morphine. A dimolecular base formed by the gentle oxidation of Morphine in alkaline solution. Name Pseudomorphine is also used for the C17 alkaloid base Once morphine had been determined to be the principal pain-killing ingredient in opium, it was substituted for opium in many treatments. Morphine's analgesic ability is due to its ability to bind and activate opioid receptors in the central nervous system (brain and spinal cord).hen morphine or another opioid analgesic binds to the opioid receptors, it reduces the neurological transfer of pain signals to the brain. Morphine mimics natural pain relievers produced by the body called endorphins. When these natural pain-relieving compounds were discovered in the 1970s, the word endorphin was coined from the words endogenous and morphine. Morphine is the most important opium alkaloid,found in the poppy plant (Papaver somniferumL.). It is obtained by extracting thedried latex of poppy. It is also obtained fromopium, which is an air-dried milky exudate ofthe same plant produced by incising unripecapsules. Opium contains about 9–14% ofmorphine. It is used in medicine for its narcoticanalgesic, anesthetic, and pain-reliefactions.
Indications Morphine is mainly used to treat both acute and chronic severe pain. It is also used for pain caused by myocardial infarction and for labor pains. Morphine relieves pulmonary edema symptoms; anesthesia and preoperative administration can make the patient quiet and drowsy; compound formula of morphine was used for acute and chronic diarrhea.
Therapeutic Function Narcotic analgesic, Sedative
Clinical Use Morphine remains the standard by which other analgesic drugs are compared. The predominant effects of morphine are at the μ-opioid receptor, although it interacts with other opioid receptors as well. Morphine is indicated for the treatment of moderate to severe and chronic pain. It is useful preoperatively for sedation,anxiolytic effects, and to reduce the dose of anesthetics. Morphine is the drug of choice for the treatment of myocardial infarction because of its bradycardiac and vasodilatory effects. In addition, morphine is the most commonly used drug for the treatment of dyspneaassociated pulmonary edema. It is thought that morphine reduces the anxiety associated with shortness of breath in these patients along with the cardiac preload and afterload. The use of morphine via the oral route has drawbacks because of its first-pass effect; however, oral morphine has been recommended for use in cancer patients for its ease of administration. In particular, the longacting preparations of morphine, such as MS-Contin and Ora-Morph, are described as the cornerstone of pain treatment in cancer patients, either alone or in combination with nonopioids.Morphine is the most commonly used analgesic drug administered via the epidural route because it is potent, efficacious, and hydrophilic. The more hydrophilic the drug, the slower the onset and the longer the duration of action following epidural administration. Single-dose or continuous infusion of morphine is used to provide pain relief in thoracic and abdominal surgical patients and in cancer patients at high risk for developing side effects associated with systemic opioids. Since morphine does not produce anesthesia via the epidural route, the patient is able to move about normally; motor function is preserved.The drawback to epidural use of morphine is that certain types of pain are relatively unresponsive, such as that associated with visceral stimuli, as in pancreatitis, and neuropathic pain from nerve deafferentation. In addition, patients can develop respiratory depression and nausea from the rostral flow of the drug to medullary centers, although the effects are much less severe than those observed following the systemic administration of the drug, and can be alleviated by elevation of the head of the patient at a 30-degree angle. Patients may also itch because of histamine release. Patient-controlled analgesia (PCA) is an alternative method of administration of morphine.The use of an indwelling catheter allows the patient to administer the drug at frequent intervals for pain relief. PCA systems allow patients the freedom to assess the need for their own analgesia and to titrate a dose tailored to their needs. Dependence is rarely observed in patients using PCA for acute pain management.
Drug interactions Potentially hazardous interactions with other drugs Analgesics: possible opioid withdrawal with buprenorphine and pentazocine. Antibacterials: metabolism increased by rifampicin. Antidepressants: possible CNS excitation or depression with MAOIs - avoid concomitant use, and for 2 weeks after stopping MAOI; possible CNS excitation or depression with moclobemide; increased sedative effects with tricyclics. Antiepileptics: increases bioavailability of gabapentin. Antihistamines: increased sedative effects with sedating antihistamines. Antipsychotics: enhanced hypotensive and sedative effects. Antivirals: concentration possibly reduced by ritonavir. Dopaminergics: avoid with selegiline. Nalmefene: avoid concomitant use. Sodium oxybate: enhanced effect of sodium oxybate - avoid.

Technology Process of Morphine

There total 92 articles about Morphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%