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Codeinphosphat

(-)-Codeine phosphate

HCID 5359227
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
52-28-8
Standard-SMILES
COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@@]341.O=P(O)(O)O
InChIKey
WUXLCJZUUHIXFY-FFHNEAJVSA-N
Summenformel
C18H21NO3.H3O4P
Durchschnittliche Molmasse
397,4 g/mol
Monoisotopische Masse
397,1290391

Überblick

Codeine Phosphate can cause developmental toxicity according to state or federal government labeling requirements.

Namen und Bezeichner

Bevorzugter Name
(-)-Codeine phosphate
IUPAC
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol;phosphoric acid
Lokaler Name
Codeinphosphat
Englischer Name
codeine phosphate
Summenformel
C18H22NO6P
Molmasse
397.36

Namen und Synonyme

CODEINE PHOSPHATE52-28-8Tricodein(-)-Codeine PhosphateDTXSID0024844Codeini phosphasMorphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)-, phosphateMorphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-, phosphate (1:1)EvacodeGalcodineBeproRefChem:196347
Weitere Namen anzeigen
Coducept PhosphateCodicept PhosphateCodeinePhosphate[D.D]Codeine phosphate (1:1)Phosphoric acid codeineCodeine phosphate (6CI, 7CI)Morphine 3-Methyl Ether PhosphateCodeine Phosphate (1mg/ml in Methanol)
DTXCID804844Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-, phosphate (salt), hydrate (2:2:1)Codeine phosphate bpCodeine phosphate ciiColrex compoundGSL05Y1MN6Codeine phosphate anhydrous2X585M1M3T

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
120 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
1
Schwere Atome
27
Formalladung
0
Komplexität
558

Experimentelle und physikochemische Eigenschaften

Solubilitygreater than or equal to 100 mg/mL at 61 °F (NTP, 1992)
Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point428 to 455 °F (decomposes) (NTP, 1992)
Physical DescriptionCodeine phosphate appears as colorless small crystals or white powder. Odorless. Bitter taste. Solutions are acid to litmus. pH (4% solution) 4.2-5. (NTP, 1992)
Dissociation Constants8.22

Physikochemische Eigenschaften

Schmelzpunkt
238 · 238-240°C
storage temp.
-20 °C · Controlled Substance, -20°C Freezer
Löslichkeit
Methanol (Slightly), Water (Slightly)
Aggregatzustand
solid
Stabilität
Stable, but light sensitive.
Major Application

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (95.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P318, P321, P330, P333+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Hazard Traits - Developmental Toxicity

Codeine phosphate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, phosphate (1:1) (salt), (5.alpha.,6.alpha.)-: Environment tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound include dryness of the mouth, nose and throat, urticaria, drug rash, anaphylactic shock, photosensitivity, excessive perspiration, chills, hypotension, headache, palpitations, tachycardia, extrasystoles, hemolytic anemia, thrombocytopenia, agranulocytosis, sedation, sleepiness, dizziness, disturbed coordination, fatigue, confusion, restlessness, tremor, irritability, excitation, anxiety, nervousness, insomnia euphoria, paresthesias, blurred vision, diplopia, acute labyrinthitis, tinnitus, hysteria, neuritis, convulsions, central nervous system depression, hallucinations, epigastric distress, anorexia, nausea, vomiting, diarrhea, constipation, change in urinary frequency, difficult urination, urinary retention, early menses, thickening of bronchial secretions, tightness of chest, wheezing, nasal stuffiness, respiratory depression, psychic dependence and physical dependence.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Hepatic. Codeine is a prodrug, itself inactive, but demethylated to the active morphine by the liver enzyme CYP2D6 to morphine. 70-80% of the dose undergoes glucuronidation to form codeine-6-glucuronide. This process is mediated by UDP-glucuronosyltransferase UGT2B7 and UGT2B4. 5-10% of the dose undergoes O-demethylation to morphine and 10% undergoes N-demethylation to form norcodeine. CYP2D6 mediates the biotransformation to morphine. CYP3A4 is the enzymes that mediates the conversion to norcodiene. Morphine and norcodeine are further metabolized and undergo glucuronidation. The glucuronide metabolites of morphine are morphine-3-glucuronide (M3G) and morphine-6-glucuronide (M6G). Both morphine and morphine-6-glucuronide are active and have analgesic activity. Norcodiene and M3G do not have any analgesic properties. Route of Elimination: 90% of the total dose of codeine is excreted through the kidneys, of which 10% is unchanged codeine. Half Life: Plasma half-lives of codeine and its metabolites have been reported to be approximately 3 hours.

MeSH Pharmacological Classification · 3 Einträge

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally.

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.

Verwendung und Herstellung

UsesFor treatment and management of pain (systemic). It is also used as an antidiarrheal and as a cough suppressant.

Anwendungen

VerwendenPresent in opium from 0.7% to 2.5%, depending on the source. Weak narcotic analgesic, perhaps due to conversion to morphine, with minimal hypnotic properties; potent antitussive. Controlled substance (opiate)

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Datenbank-Bezeichner

CAS
52-28-8
PubChem CID
5359227
DTXSID
DTXSID0024844
ChEMBL
CHEMBL6067642
UNII
2X585M1M3T
EC Number
200-137-8
pharmaceutical
EPA chemische Informationen
Codeine phosphate (52-28-8)
Reactive GroupAlcohols and Polyols
Reactivity Profile · 1 Eintrag

CODEINE PHOSPHATE is sensitive to exposure to light. (NTP, 1992). Materials that are acidic salts are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.

Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 3 (95.6%)

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 Eintrag

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxikologische Informationen

Treatment · 1 Eintrag

Naloxone antagonizes most effects of codeine. Protect the airway as Naloxone may induce vomiting. Naloxone has a shorter duration of action than codeine; repeated doses may be needed. Protect the patient's airway and support ventilation and perfusion. Meticulously monitor and maintain, within acceptable limits, the patient's vital signs, blood gases, serum electrolytes, etc. Absorption of drugs from the gastrointestinal tract may be decreased by giving activated charcoal, which in many cases, is more effective than emesis or lavage; consider charcoal instead of or in addition to gastric emptying. Repeated doses of charcoal over time may hasten elimination of some drugs that have been absorbed. Safeguard the patient's airway when employing gastric emptying or charcoal. (L1712)

Health EffectsMedical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
Exposure Routes · 1 Eintrag

Oral, Intramuscular. Well absorbed following oral administration with a bioavailability of approximately 90%. Maximum plasma concentration occurs 60 minutes post-administration. Food does not effect the rate or extent of absorption of codeine.

Toxicity Summary · 1 Eintrag

Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Codeine's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

Signs and SymptomsRespiratory depression, sedation and miosis and common symptoms of overdose. Other symptoms include nausea, vomiting, skeletal muscle flaccidity, bradycardia, hypotension, and cool, clammy skin. Apnea and death may ensue.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
WGK 3
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 Oral

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

4-Hydroxy-3-methoxy-17-methylmorphinan-6-on