Anileridine

Title: Anileridine
CAS Registry Number: 144-14-9
CAS Name: 1-[2-(4-Aminophenyl)ethyl]-4-phenyl-4-piperidinecarboxylic acid ethyl ester
Additional Names: 1-(p-aminophenethyl)-4-phenylisonipecotic acid ethyl ester; ethyl 1-(4-aminophenethyl)-4-phenylisonipecotate; N-[b-(p-aminophenyl)ethyl]-4-phenyl-4-carbethoxypiperidine; N-b-(p-aminophenyl)ethylnormeperidine
Trademarks: Leritine (Merck & Co.)
Molecular Formula: C22H28N2O2
Molecular Weight: 352.47
Percent Composition: C 74.97%, H 8.01%, N 7.95%, O 9.08%
Literature References: Synthesis: Weijlard et al., J. Am. Chem. Soc. 78, 2342 (1956); US 2966490 (1960 to Merck & Co.).
Properties: Mp 83°.
Derivative Type: Dihydrochloride
CAS Registry Number: 126-12-5
Molecular Formula: C22H28N2O2.2HCl
Molecular Weight: 425.39
Percent Composition: C 62.12%, H 7.11%, N 6.59%, O 7.52%, Cl 16.67%
Properties: Crystals from methanol + ether, mp 280-287° (dec). Freely soluble in water, methanol. Solubility in ethanol: 8 mg/g. pH of aq solns 2.0 to 2.5. Solns are stable at pH 3.5 and below. At pH 4 and higher the insol free base is precipitated. uv max (pH 7 in 90% methanol contg phosphate buffer): 235, 289 nm (A1%1cm 293, 34.5). Distribution coefficient (water, pH 3.6/n-butanol): 0.9.
Melting point: mp 280-287° (dec)
Absorption maximum: uv max (pH 7 in 90% methanol contg phosphate buffer): 235, 289 nm (A1%1cm 293, 34.5)
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Aniline Aniline Mustard Anilinephthalein Anise Alcohol Anisidine

Anileridine
Anileridine.svg
Systematic (IUPAC) name
Ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
Clinical data
AHFS/Drugs.com monograph
Legal status Controlled (S8) (AU) -only (CA) Schedule II (US)
Routes Tablets, injection
Pharmacokinetic data
Protein binding > 95%
Metabolism Hepatic
Identifiers
CAS number 144-14-9 YesY
ATC code N01AH05
PubChem CID 8944
DrugBank DB00913
ChemSpider 8600 YesY
UNII 71Q1A3O279 YesY
KEGG D02941 YesY
ChEBI CHEBI:61203 YesY
ChEMBL CHEMBL1201347 N
Chemical data
Formula C22H28N2O2 
Mol. mass 352.47 g/mol
Physical data
Melt. point 83 °C (181 °F)
 N (what is this?)  (verify)

Anileridine (trade name: Leritine) is a synthetic analgesic drug and is a member of the piperidine class of analgesic agents developed by Merck & Co. in the 1950s.[1] It differs from pethidine (meperidine) in that the N-methyl group of meperidine is replaced by an N-aminophenethyl group, which increases its analgesic activity.

Anileridine is no longer manufactured in the US or Canada.[2]