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Anileridine

HCID 8944
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
144-14-9
Standard SMILES
CCOC(=O)C1(c2ccccc2)CCN(CCc2ccc(N)cc2)CC1
InChIKey
LKYQLAWMNBFNJT-UHFFFAOYSA-N
Molecular formula
C22H28N2O2
Average molar mass
352.5 g/mol
Monoisotopic mass
352.21507814

Overview

Anileridine is a piperidinecarboxylate ester that is the ethyl ester of isonipecotic acid in which the hydrogen alpha- to the carboxyl group is substituted by a phenyl group, and the hydrogen attached to the nitrogen is substituted by a 2-(4-aminophenyl)ethyl group. It has a role as an opioid analgesic and an opioid receptor agonist. It is an ethyl ester, a piperidinecarboxylate ester and a substituted aniline. It is functionally related to a N-[2-(4-aminophenyl)ethyl]-4-phenylisonipecotic acid. It is a conjugate base of an anileridine(2+).

Names & identifiers

Preferred name
Anileridine
IUPAC
ethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylate
English name
Anileridine
Molecular formula
C22H28N2O2
Molecular weight
352.47

Names & synonyms

ANILERIDINENipecotanAlidineLeritinAdopolApidolAnileridinaAnileridinum144-14-9Ethyl 1-(p-aminophenethyl)-4-phenylisonipecotateethyl 1-[2-(4-aminophenyl)ethyl]-4-phenylpiperidine-4-carboxylateN-beta-(p-Aminophenyl)ethylnormeperidine
Show more names
Adopol-d4Ethyl 1-(4anileridine baseLKYQLAWMNBFNJT-UHFFFAOYSA-NAnileridine (1 mg/mL in ethyl acetate)Anileridine (1.0 mg/mL in ethyl acetate)1-(p-AMinophenethyl)-4-phenylisonipecotic Acid Ethyl Ester
Ethyl 1-(4-aminophenethyl)-4-phenylisonipecotateDTXSID8022610N-(beta-(p-Aminophenyl)ethyl)-4-phenyl-4-carbethoxypiperidineEthyl 1-(2-(4-aminophenyl)ethyl)-4-phenyl-4-piperidinecarboxylateIDS-NA-012Isonipecotic acid, 1-(p-aminophenethyl)-4-phenyl-, ethyl ester1-(p-Aminophenethyl)-4-phenylpiperidine-4-carboxylic acid ethyl ester4-Piperidinecarboxylic acid, 1-(2-(4-aminophenyl)ethyl)-4-phenyl-, ethyl ester

Database identifiers

CAS
144-14-9

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
55.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
7
Heavy atoms
26
Formal charge
0
Complexity
431

Experimental & physicochemical properties

Drugs · 4 items

DEA NFLIS-Drug Category -> Narcotic Analgesics

DEA Schedule II Controlled Substance -> Opiates

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP3.7
OdorODORLESS TO PRACTICALLY ODORLESS
TasteSLIGHTLY BITTER TASTE
Color/Form · 2 items

WHITE CRYSTALLINE POWDER

WHITE TO YELLOWISH WHITE CRYSTALLINE POWDER

Solubility · 5 items

ODORLESS; PH (1 IN 20 SOLN) BETWEEN 2.5 & 3; PRACTICALLY INSOL IN ETHER & CHLOROFORM /ANILERIDINE DIHYDROCHLORIDE/

SOL IN ALCOHOL, CHLOROFORM; VERY SLIGHTLY SOL IN WATER

SOL IN ETHER

Sol in 1 in 2 parts of alcohol and 1 in 1 of chloroform.

1.24e-02 g/L

Melting Point · 3 items

275-277

83 °C

83 °C

Physical DescriptionSolid

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory InformationDEA schedule II controlled substance
Other Safety InformationIMAP assessments - 4-Piperidinecarboxylic acid, 1-[2-(4-aminophenyl)ethyl]-4-phenyl-, ethyl ester: Environment tier I assessment
FDA Requirements · 4 items

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 amended; 21 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 #9020; Drug class: Opiate.

Drugs; statement 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/

Safety & protection

Storage ConditionsAnileridine 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.

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Protein Binding> 95%
Pharmacodynamics · 1 item

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.

Mechanism of Action · 2 items

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.

ACUTE ADMIN OF ANILERIDINE PHOSPHATE INCR BRAIN LEVELS OF 3-METHOXY-4-HYDROXYPHENYLETHYLENE GLYCOL SULFATE IN RATS IN DOSE-DEPENDENT MANNER. INCR IN BRAIN NOREPINEPHRINE TURNOVER MAY BE SPECIFIC ACTION OF NARCOTIC ANALGESICS.

Metabolism/Metabolites · 3 items

Hepatic

ANILERIDINE YIELDS P-AMINOPHENYLACETIC ACID & NORMEPERIDINE IN RATS. /FROM TABLE/

Hepatic

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
8944
DTXSID
DTXSID8022610
ChEMBL
CHEMBL1201347
ChEBI
CHEBI:61203
UNII
71Q1A3O279
Nikkaji
J5.827K
Stability/Shelf Life · 3 items

STABLE IN AIR /ANILERIDINE DIHYDROCHLORIDE/

OXIDIZES & DARKENS BOTH IN AIR & ON EXPOSURE TO LIGHT

SOLUTIONS ARE STABLE @ PH 3.5 & BELOW; @ PH 4 & HIGHER INSOL FREE BASE IS PRECIPITATED /ANILERIDINE DIHYDROCHLORIDE/

Other Experimental Properties · 2 items

EXHIBITS POLYMORPHIS AND OF 2 CRYSTALLINE FORMS OBSERVED, 1 MELTS @ ABOUT 80 °C & OTHER @ ABOUT 89 °C

CRYSTALS FROM METHANOL + ETHER; DECOMP @ 280-287 °C; PH OF AQ SOLN 2.0-2.5; MAX ABSORPTION (PH 7 IN 90% METHANOL CONTAINING PHOSPHATE BUFFER): 235, 289 NM (ABSORBANCE = 293, 34.5, 1%, 1 CM); FREELY SOL IN WATER, METHANOL; SOL IN ETHANOL: 8 MG/G; DISTRIBUTION COEFFICIENT BETWEEN WATER @ PH 3.6 & N-BUTANOL= 0.9 /ANILERIDINE DIHYDROCHLORIDE/

Physicochemical properties

Melting point
83 °C · 83°C
Boiling point
486.07 °C · 486.07°C (rough estimate)
Density
1.1096 · 1.1096 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
solubility
DMSO (Slightly), Ethyl Acetate (Soluble)
pka
8.41 · 8.41±0.10(Predicted)
form
Solid
FDA UNII
71 Q1A3O279 · 71Q1A3O279
RIDADR
1544 · 1544
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Hazardous Substances Data
144 · 144-14-9(Hazardous Substances Data)
Toxicity
50 orl-rat: · LD50 orl-rat: 175 mg/kg 27ZIAQ -,-,65

Toxicology

Interactions · 3 items

... 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.

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 RoutesAnileridine is absorbed by all routes of administration.
Toxicity Summary · 1 item

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 SymptomsSymptoms 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 · 5 items

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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

anileridine

DILI Negative

Oral, Intramuscular; Intravenous; Subcutaneous

DOI:10.1016/j.drudis.2019.09.022

Non-Human Toxicity Excerpts · 1 item

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.

Regulatory information

FDA Requirements · 4 items

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 amended; 21 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 #9020; Drug class: Opiate.

Drugs; statement 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/

Safety data

ridadr
1544
Toxicity
LD50 orl-rat: 175 mg/kg 27ZIAQ -,-,65
hazard_class
6.1(b)
packing_group
III
Hazardous Substances Data
144-14-9(Hazardous Substances Data)
Absorption, Distribution and Excretion
Anileridine is absorbed by all routes of administration.
Cellular LocationsMembrane
Metabolite PathwaysAnileridine Action Pathway

Uses & manufacturing

Uses · 2 items

MEDICATION

For treatment and management of pain (systemic) and for use as an anesthesia adjunct.

Methods of Manufacturing · 2 items

ETHYL 4-PHENYLISONIPECOTATE IS HEATED WITH P-NITROPHENETHYL BROMIDE & SODIUM CARBONATE IN ETHANOL SOLN & RESULTING ETHYL 1-(P-NITROPHENETHYL)-4-PHENYLISONIPECOTATE IS HYDROGENATED TO ANILERIDINE OVER PALLADIUM-CHARCOAL.

ANILERIDINE IS DISSOLVED IN ETHANOL CONTAINING HYDROGEN CHLORIDE, & DIHYDROCHLORIDE IS ALLOWED TO CRYSTALLIZE. /DIHYDROCHLORIDE/

Formulations/Preparations · 4 items

ANILERIDINE HYDROCHLORIDE, NATIONAL FORMULARY (LERITINE), IS AVAILABLE AS 25-MG TABLETS. ANILERIDINE INJECTION, NATIONAL FORMULARY, IS MARKETED FOR PARENTERAL ADMIN IN AMPULS & MULTIPLE-DOSE VIALS CONTAINING 25 MG/ML OF ANILERIDINE PHOSPHATE.

Anilerdine Hydrochloride Tablets USP ... contain an amount of anileridine equivalent to the labeled amount of anileridine, within + or - 5%. Meet the requirements for Identification, Dissolution (65% in 45 minutes in 0.1 N hydrochloric acid in Apparatus 1 at 100 rpm), and Uniformity of dosage units. /Anileridine hydrochloride/

Anileridine USP ... contains not less than 98.5% and not more than 101.0% of anileridine, calculated on the anhydrous basis. Meets the requirements for Identification, Water (not more than 1.0%). Residue on ignition (not more than 0.1%), and chloride (0.040).

Anileridine Injection USP ... A sterile solution of Anileridine in Water for Injection, prepared with the aid of Phosphoric Acid. Contains the labeled ammont as the phosphate within -10% to +15%. Meets the requirements for Identification, Bacterial endotoxins, pH (4.5-5.0), and Injections. /Anileridine phosphate/

General Manufacturing Information · 2 items

NARCOTIC ANALGESICS PRODUCE MORPHINE-TYPE DRUG DEPENDENCE & ARE INCL IN SCHEDULE II OF COMPREHENSIVE DRUG ABUSE PREVENTION & CONTROL ACT OF 1970. ... SYNTHETIC MORPHINE-LIKE COMPD CAN BE CLASSIFIED BY CHEMICAL STRUCTURE: (1) PHENYLPIPERIDINE DERIV ... ANILERIDINE [LERITENE].

Anileridine /is/ not commercially available in the United States.

Applications

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

Upstream & downstream products

Upstream raw materials

Hydrochloric acidSodium carbonate
Additional notes · 1 item

DefinitionChEBI: A piperidinecarboxylate ester that is the ethyl ester of isonipecotic acid in which the hydrogen alpha- to the carboxyl group is substituted by a phenyl group, and the hydrogen attached to the nitrogen is substituted by a 2-(4-aminophenyl) thyl group.