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Anileridine
Adopol · Apidol · Alidine · Adopol-d4 · Ethyl 1-(4 · anileridine base · LKYQLAWMNBFNJT-UHFFFAOYSA-N · Anileridine (1 mg/mL in ethyl acetate)
Identifikatoren & physikalische Daten
| CAS No. | 144-14-9 |
|---|---|
| Summenformel | C22H28N2O2 |
| Durchschnittliche Molmasse | 352,5 g/mol |
| Monoisotopische Masse | 352,21507814 g/mol |
| SMILES | CCOC(=O)C1(c2ccccc2)CCN(CCc2ccc(N)cc2)CC1 |
| InChIKey | LKYQLAWMNBFNJT-UHFFFAOYSA-N |
| PubChem CID | 8944 |
| ChEMBL | CHEMBL1201347 |
| ChEBI | CHEBI:61203 |
| DTXSID | DTXSID8022610 |
Chemische & physikalische Eigenschaften
| XLogP | 3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 431 |
| Arzneimittel | DEA NFLIS-Drug Category -> Narcotic AnalgesicsDEA Schedule II Controlled Substance -> OpiatesPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| LogP (Verteilungskoeffizient) | 3.7 |
| Geruch | ODORLESS TO PRACTICALLY ODORLESS |
| Geschmack | SLIGHTLY BITTER TASTE |
| Color/Form | WHITE CRYSTALLINE POWDERWHITE TO YELLOWISH WHITE CRYSTALLINE POWDER |
| Löslichkeit | ODORLESSPH (1 IN 20 SOLN) BETWEEN 2.5 & 3PRACTICALLY INSOL IN ETHER & CHLOROFORM /ANILERIDINE DIHYDROCHLORIDE/SOL IN ALCOHOL, CHLOROFORMVERY SLIGHTLY SOL IN WATERSol in 1 in 2 parts of alcohol and 1 in 1 of chloroform.1.24e-02 g/LDMSO (Slightly), Ethyl Acetate (Soluble) |
| Schmelzpunkt | 275-27783 °C83°C |
| Physical Description | Solid |
| Stability/Shelf Life | STABLE IN AIR /ANILERIDINE DIHYDROCHLORIDE/OXIDIZES & DARKENS BOTH IN AIR & ON EXPOSURE TO LIGHTSOLUTIONS ARE STABLE @ PH 3.5 & BELOW@ PH 4 & HIGHER INSOL FREE BASE IS PRECIPITATED /ANILERIDINE DIHYDROCHLORIDE/ |
| Other Experimental Properties | EXHIBITS POLYMORPHIS AND OF 2 CRYSTALLINE FORMS OBSERVED, 1 MELTS @ ABOUT 80 °C & OTHER @ ABOUT 89 °CCRYSTALS FROM METHANOL + ETHERDECOMP @ 280-287 °CPH OF AQ SOLN 2.0-2.5MAX ABSORPTION (PH 7 IN 90% METHANOL CONTAINING PHOSPHATE BUFFER): 235, 289 NM (ABSORBANCE = 293, 34.5, 1%, 1 CM)FREELY SOL IN WATER, METHANOLSOL IN ETHANOL: 8 MG/GDISTRIBUTION COEFFICIENT BETWEEN WATER @ PH 3.6 & N-BUTANOL= 0.9 /ANILERIDINE DIHYDROCHLORIDE/ |
| Siedepunkt | 486.07°C (rough estimate) |
| Dichte | 1.1096 (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| pKa (Säurekonstante) | 8.41±0.10(Predicted) |
| Aggregatzustand | Solid |
Sicherheit & Vorschriften
| Regulatorische Informationen | DEA schedule II controlled substance |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - 4-Piperidinecarboxylic acid, 1-[2-(4-aminophenyl)ethyl]-4-phenyl-, ethyl ester: Environment tier I assessment |
| FDA-Anforderungen | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule II includes anileridine, DEA Code #9020Drug class: Opiate.Drugsstatement of required warning. The label of any drug listed as a "controlled substance" in schedule II, III, or IV of the Federal Controlled Substances Act shall, when dispensed to or for a patient, contain the following warning: "Caution: Federal law prohibits the transfer of this drug to any person other than the patient for whom it was prescribed." This statement is not required to appear on the label of a controlled substance for use in clinical investigations which are "blind".The Discontinued Drug Product List identifies discontinued drug products including anileridine hydrochloride and anileridine phosphate (Leritine, Merck Sharp and Dohme). The List contains products that have never been marketed, products discontinued from marketing or products that have had their approval withdrawn for other than safety or effectiveness reasons. /Anileridinie hydrochloride and phosphate/ |
| Lagerbedingungen | Anileridine USP /and Anileridine Hydrochloride USP/ - Preserve in tight, light-resistant containers. ... Anileridine Injection USP - Preserve in single dose or in multiple-dose containers, preferably of Type I glass, protected from light. |
| Wechselwirkungen | ... CONCOMITANT ADMIN OF AMPHETAMINE HAS BEEN REPORTED TO ENHANCE ANALGESIC EFFECTS OF MEPERIDINE & ITS CONGENERS. /MEPERIDINE/ACUTE ADMIN OF ANILEIDINE PHOSPHATE INCR BRAIN LEVELS OF 3-METHOXY-4-HYDROXYPHENYLETHYLENE GLYCOL SULFATE IN RATS. INCR WAS ANTAGONIZED BY MALOXONE.IN MICE, PHENELZINE HYDROGEN SULFATE PRETREATMENT DID NOT AFFECT (+-)-ANILERIDINE-HCL. |
| Gesundheitliche Auswirkungen | Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose. |
| Expositionspfade | Anileridine is absorbed by all routes of administration. |
| Toxizitätsübersicht | 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. Opioids such as anileridine 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 Symptoms | Symptoms of overexposure include dizziness, perspiration, a feeling of warmth, dry mouth, visual difficulty, itching, euphoria, restlessness, nervousness and excitement have been reported. |
| Human Toxicity Excerpts | Addictive.ADVERSE EFFECTS ... OF ANILERIDINE ARE SIMILAR TO THOSE OF MEPERIDINE.UNTOWARD EFFECTS THAT MAY OCCUR AFTER THERAPEUTIC DOSES OF MEPERIDINE ... INCL DIZZINESS, SWEATING, EUPHORIA, DRY MOUTH, NAUSEA, VOMITING, WEAKNESS, VISUAL DISTURBANCES, PALPITATION, DYSPHORIA, SYNCOPE, & SEDATION. /MEPERIDINE/FATAL COMBINED ANILERIDINE-PETHIDINE POISONING.May be habit forming. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)anileridineDILI NegativeOral, IntramuscularIntravenousSubcutaneousDOI:10.1016/j.drudis.2019.09.022 |
| Non-Human Toxicity Excerpts | EFFECTS OF ANILERIDINE-2HCL ON SQUIRREL MONKEY WHOSE BEHAVIOR WAS MAINTAINED UNDER 2.0-S SCHEDULE OF SHOCK INCREMENT. RESPONSES WERE DOSE RELATED. @ ONE DOSE LEVEL THERE WAS DECR RESPONDING @ 0 SHOCK INTENSITY & @ ANOTHER INCR RESPONDING PLUS CONVULSIONS. |
| UN-Transportnummer | 1544 |
| Toxizität | LD50 orl-rat: 175 mg/kg 27ZIAQ -,-,65 |
| Gefahrenklasse | 6.1(b) |
| Verpackungsgruppe | III |
| Gefahrstoffdaten | 144-14-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
A synthetic analgesic drug. 4-phenylpiperidine derivative that is an analog of Meperidine (M223900) with increased analgesic activity.