Anileridine (CHEM002301)

Record Information
Version1.0
Creation Date2009-07-21 20:27:57 UTC
Update Date2026-05-14 16:52:39 UTC
Accession NumberCHEM002301
Identification
Common NameAnileridine
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Analgesic
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Narcotic
  • Opiate Agonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlic acid ethyl esterChEBI
AnileridinaChEBI
AnileridinumChEBI
Ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylateChEBI
Ethyl 1-(4-aminophenethyl)-4-phenylisonipecotateChEBI
Ethyl 1-(p-aminophenethyl)-4-phenylisonipecotateChEBI
N-(beta-(p-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineChEBI
N-beta-(p-Aminophenyl)ethylnormeperidineChEBI
1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxlate ethyl esterGenerator
Ethyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylic acidGenerator
Ethyl 1-(4-aminophenethyl)-4-phenylisonipecotic acidGenerator
Ethyl 1-(p-aminophenethyl)-4-phenylisonipecotic acidGenerator
N-(b-(p-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineGenerator
N-(Β-(p-aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineGenerator
N-b-(p-Aminophenyl)ethylnormeperidineGenerator
N-Β-(p-aminophenyl)ethylnormeperidineGenerator
PhthalylsulfathiazoleHMDB
SulfathalidineHMDB
Anileridine monohydrochlorideHMDB
Anileridine hydrochlorideHMDB
Anileridine phosphateHMDB
Anileridine phosphate (1:1)HMDB
Anileridine dihydrochlorideHMDB
Chemical FormulaC22H28N2O2
Average Molecular Mass352.470 g/mol
Monoisotopic Mass352.215 g/mol
CAS Registry Number144-14-9
IUPAC Nameethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
Traditional Nameanileridine
SMILESCCOC(=O)C1(CCN(CCC2=CC=C(N)C=C2)CC1)C1=CC=CC=C1
InChI IdentifierInChI=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
InChI KeyLKYQLAWMNBFNJT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Phenethylamine
  • Piperidinecarboxylic acid
  • Aniline or substituted anilines
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point275-277°C
Boiling PointNot Available
Solubility1.24e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.05ALOGPS
logP3.64ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)8.88ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.56 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity106.55 m³·mol⁻¹ChemAxon
Polarizability40.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureAnileridine is absorbed by all routes of administration.
Mechanism of ToxicityOpiate 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.
MetabolismHepatic
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor treatment and management of pain (systemic) and for use as an anesthesia adjunct.
Minimum Risk LevelNot Available
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.
SymptomsSymptoms of overexposure include dizziness, perspiration, a feeling of warmth, dry mouth, visual difficulty, itching, euphoria, restlessness, nervousness and excitement have been reported.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00913
HMDB IDHMDB0015049
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAnileridine
Chemspider ID8600
ChEBI ID61203
PubChem Compound ID8944
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Weijlard, J.and Pfister, K., Ill; US. Patent 2,966,490; December 27, 1960; assigned to Merck & Co., Inc.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=581295
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=779391
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=779392