pethidine (CHEBI:6754)

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ChEBI Name	pethidine

ChEBI ID	CHEBI:6754

Definition	A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C15H21NO2

Net Charge

Average Mass

247.338

Monoisotopic Mass

247.15723

InChI

InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3

InChIKey

XADCESSVHJOZHK-UHFFFAOYSA-N

SMILES

C1(C(=O)OCC)(CCN(CC1)C)C2=CC=CC=C2

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. kappa-opioid receptor agonist A compound that exhibits agonist activity at the kappa-opioid receptor. mu-opioid receptor agonist A compound that exhibits agonist activity at the mu-opioid receptor.

Application(s):	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. kappa-opioid receptor agonist A compound that exhibits agonist activity at the kappa-opioid receptor. mu-opioid receptor agonist A compound that exhibits agonist activity at the mu-opioid receptor. antispasmodic drug A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.

ChEBI Ontology
Outgoing	pethidine (CHEBI:6754) has role κ-opioid receptor agonist (CHEBI:59282) pethidine (CHEBI:6754) has role μ-opioid receptor agonist (CHEBI:55322) pethidine (CHEBI:6754) has role antispasmodic drug (CHEBI:53784) pethidine (CHEBI:6754) has role opioid analgesic (CHEBI:35482) pethidine (CHEBI:6754) is a ethyl ester (CHEBI:23990) pethidine (CHEBI:6754) is a piperidinecarboxylate ester (CHEBI:48630) pethidine (CHEBI:6754) is a tertiary amino compound (CHEBI:50996) pethidine (CHEBI:6754) is conjugate base of pethidine(1+) (CHEBI:149471)

Incoming	pethidine(1+) (CHEBI:149471) is conjugate acid of pethidine (CHEBI:6754)

IUPAC Name

ethyl 1-methyl-4-phenylpiperidine-4-carboxylate

Synonyms	Sources
1-methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester	ChEBI
1-methyl-4-phenylisonipecotic acid ethyl ester	ChemIDplus
1-methyl-4-phenylpiperidine-4-carboxylic acid ethyl ester	ChemIDplus
ethyl 1-methyl-4-phenylisonipecotate	ChemIDplus
IDS-NP-001	DrugBank
isonipecaine	DrugCentral
isonipecaïne	DrugBank
meperidina	DrugBank
meperidine	KEGG COMPOUND
methyl phenylpiperidine carbonic acid ethyl ester	ChemIDplus
N-methyl-4-phenyl-4-carbethoxypiperidine	ChemIDplus
pethidin	DrugBank
pethidineter	ChemIDplus
petydyna	ChemIDplus
phetidine	ChemIDplus

Last Modified

15 April 2020