ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate

• ChemBase ID: 789
• Molecular Formular: C22H28N2O2
• Molecular Mass: 352.46992
• Monoisotopic Mass: 352.21507815
• SMILES: O(C(=O)C1(CCN(CC1)CCc1ccc(N)cc1)c1ccccc1)CC
• Canonical SMILES: CCOC(=O)C1(CCN(CC1)CCc1ccc(cc1)N)c1ccccc1
• InChI: InChI=1S/C22H28N2O2/c1-2-26-21(25)22(19-6-4-3-5-7-19)13-16-24(17-14-22)15-12-18-8-10-20(23)11-9-18/h3-11H,2,12-17,23H2,1H3
• InChIKey: LKYQLAWMNBFNJT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
• IUPAC Traditional name: anileridine
• Brand Name: Adopol; Alidine; Apidol; Apodol; Leritin; Leritine; Nipecotan
• Synonyms: 1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxylic Acid Ethyl Ester; 1-(p-Aminophenethyl)-4-phenylisonipecotic Acid Ethyl Ester; 1-(p-Aminophenethyl)-4-phenylpiperidine-4-carboxylic Acid Ethyl Ester; Adopol; Alidine; Apidol; Ethyl 1-(4-Aminophenethyl)-4-phenylisonipecotate; Leritin; Leritine; Nipecotan; Anileridina [INN-Spanish]; Anileridinum [INN-Latin]; Phthalylsulfathiazole; Sulfathalidine; Anileridine

Database IDs

• CAS Number: 144-14-9
• PubChem SID: 160964252; 46505199
• PubChem CID: 8944
• CHEBI ID: 61203
• ATC CODE: N01AH05
• CHEMBL: 1201347
• Chemspider ID: 8600
• DrugBank ID: DB00913
• KEGG ID: D02941
• Unique Ingredient Identifier: 71Q1A3O279
• Wikipedia Title: Anileridine

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.47604656
• LogD (pH = 7.4): 2.1516032
• Log P: 3.6400087
• Molar Refractivity: 106.5517 cm^3
• Polarizability: 40.97784 Å^3
• Polar Surface Area: 55.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.05
• LOG S: -4.46
• Solubility (Water): 1.24e-02 g/l

PROPERTIES

Physical Property

• Melting Point: 83°C (181.4°F)
• Hydrophobicity(logP): 3.7

Pharmacology Properties

• Admin Routes: Tablets, injection
• Metabolism: Hepatic
• Protein Bound: > 95%
• Legal Status: Rx-only (Canada); Schedule II (US)

DETAILS

DrugBank - DB00913

• Drug Groups: illicit; approved
• Description: Anileridine is a synthetic opioid and strong analgesic medication. It is a narcotic pain reliever used to treat moderate to severe pain. Narcotic analgesics act in the central nervous system (CNS) to relieve pain. Some of their side effects are also caused by actions in the CNS.
• Indication: For treatment and management of pain (systemic) and for use as an anesthesia adjunct.
• Pharmacology: Anileridine, a potent analgesic, is an analog of pethidine. Anileridine is useful for the relief of moderate to severe pain. It may also be used as an analgesic adjunct in general anesthesia in the same manner as meperidine to reduce the amount of anesthetic needed, to facilitate relaxation, and to reduce laryngospasm. In addition, anileridine exerts mild antihistaminic, spasmolytic and antitussive effects. Anileridine's main pharmacologic action is exerted on the CNS. Respiratory depression, when it occurs, is of shorter duration than that seen with morphine or meperidine when equipotent analgesic doses are used.
• Toxicity: Symptoms of overexposure include dizziness, perspiration, a feeling of warmth, dry mouth, visual difficulty, itching, euphoria, restlessness, nervousness and excitement have been reported.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Anileridine is absorbed by all routes of administration.
• Protein Binding: > 95%
• External Links: Wikipedia

Toronto Research Chemicals - A660750

A synthetic analgesic drug. 4-phenylpiperidine derivative that is an analog of Meperidine (M223900) with increased analgesic activity.

REFERENCES

• Freeman, D.S. et al.: J. Pharamcol. Exp. Therap., 203, 203 (1977)
• Abbit, F.V.: Phamacol. Biochem. Behav., 24, 1247 (1977)