ChemFOnt: Showing chemical card for Normeperidine (CFc000022781)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:15:14 UTC

Chemfont ID

CFc000022781

Molecule Identification

Common Name

Normeperidine

Definition

Pethidine (INN) or meperidine hydrochloride (USAN) (commonly referred to as Demerol in the US but also referred to as: isonipecaine; lidol; pethanol; piridosal; Algil; Alodan; Centralgin; Dispadol; Dolantin; Mialgin (in Indonesia); Petidin Dolargan (in Poland); Dolestine; Dolosal; Dolsin; Mefedina) is a fast-acting opioid analgesic drug. Pethidine is quickly hydrolysed in the liver to pethidinic acid and is also demethylated to norpethidine, which has half the analgesic activity of pethidine but a longer elimination half-life (8-12 hours); accumulating with regular administration, or in renal failure. Norpethidine is toxic and has convulsant and hallucinogenic effects. The toxic effects mediated by the metabolites cannot be countered with opioid receptor antagonists such as naloxone or naltrexone and are probably primarily due to norpethidine's anticholinergic activity probably due to its structural similarity to atropine though its pharmacology has not been thoroughly explored. The neurotoxicity of pethidine's metabolites is a unique feature of pethidine compared to other opioids. Pethidine's metabolites are further conjugated with glucuronic acid and excreted into the urine.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-(Ethoxycarbonyl)-4-phenylpiperidine	HMDB
4-Carbethoxy-4-phenylpiperidine	HMDB
4-Phenyl-4-carbethoxypiperidine	HMDB
Ethyl 4-phenyl-4-piperidinecarboxylate	HMDB
Ethyl 4-phenylisonipecotate	HMDB
Ethyl 4-phenylpiperidine-4-carboxylate	HMDB
Isonipecotic acid, 4-phenyl-, ethyl ester	HMDB
Nordolsin	HMDB
Norpethidine	HMDB
Normeperidine carbonate (2:1)	HMDB
Normeperidine hydrochloride	HMDB
Normeperidine, 3H-labeled CPD	HMDB
Ethyl 4-phenylpiperidine-4-carboxylic acid	HMDB
Normeperidine	MeSH

Chemical Formula

C₁₄H₁₉NO₂

Average Molecular Weight

233.3062

Monoisotopic Molecular Weight

233.141578857

IUPAC Name

ethyl 4-phenylpiperidine-4-carboxylate

Traditional Name

norpethidine

CAS Registry Number

77-17-8

SMILES

CCOC(=O)C1(CCNCC1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3

InChI Key

QKHMFBKXTNQCTM-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Piperidinecarboxylic acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041958)

Source

Endogenous

Endogenous (HMDB: HMDB0041958)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	1.45	ALOGPS
logP	2.07	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.19 m³·mol⁻¹	ChemAxon
Polarizability	26.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041958

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pethidine

METLIN ID

Not Available

PubChem Compound

32414

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Normeperidine (CFc000022781)

MOL for CFc000022781 (Normeperidine)

3D MOL for CFc000022781 (Normeperidine)

3D SDF for CFc000022781 (Normeperidine)

3D-SDF for CFc000022781 (Normeperidine)

PDB for CFc000022781 (Normeperidine)

3D PDB for CFc000022781 (Normeperidine)

SMILES for CFc000022781 (Normeperidine)

INCHI for CFc000022781 (Normeperidine)

Structure for CFc000022781 (Normeperidine)

3D Structure for CFc000022781 (Normeperidine)