ContaminantDB: Meperidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (15)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:56 UTC

Update Date

2016-11-09 01:08:42 UTC

Accession Number

CHEM002197

Identification

Common Name

Meperidine

Class

Small Molecule

Description

A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Adjuvant
Adjuvant, Anesthesia
Amine
Analgesic
Analgesic, Opioid
Drug
Ester
Ether
Metabolite
Narcotic
Opiate Agonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Pethidine	Kegg
Pethidine DBL	Kegg
Dolantin	HMDB
Dolcontral	HMDB
Operidine epj-I	HMDB
Lydol	HMDB
Dolargan	HMDB
Dolin	HMDB
Dolosal	HMDB
Operidine epj I	HMDB
Demerol	HMDB
Dolsin	HMDB
Isonipecain	HMDB
Lidol	HMDB
Meperidine hydrochloride	HMDB

Chemical Formula

C₁₅H₂₁NO₂

Average Molecular Mass

247.333 g/mol

Monoisotopic Mass

247.157 g/mol

CAS Registry Number

57-42-1

IUPAC Name

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

Traditional Name

meperidine

SMILES

CCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C1

InChI Identifier

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

InChI Key

XADCESSVHJOZHK-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
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:6754 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	270°C
Boiling Point	Not Available
Solubility	3220 mg/L (at 30°C)

Predicted Properties

Property	Value	Source
Water Solubility	1.11 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.46	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	8.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.48 m³·mol⁻¹	ChemAxon
Polarizability	28.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dl-9310000000-9f5598127b487d9339dc	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0090000000-bcf24d9e6302b6454d0e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dl-9310000000-9f5598127b487d9339dc	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0002-0090000000-bcf24d9e6302b6454d0e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1900000000-ea19250f67bb7f684380	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0090000000-2d9035995cbed82a8382	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0190000000-96507adebcd15f1cb917	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-1490000000-d1e318ddf3f73eb8db30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-7970000000-d3f460862fa9a6d8be1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-8910000000-b45b7154182933942536	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00dl-9800000000-e79c047f6c6a8c9c0033	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-00dl-9700000000-121bbb952edc449abb75	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-9810000000-1ecfa38f326384b22b6c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-0090000000-32a2416ef149cdf6e2ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-0190000000-553d10a55d1124382fb3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-7970000000-ca6d994cd203c94bf4aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-1490000000-d1b086505c982e77f305	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0190000000-75ce42839d066b768d84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uka-1390000000-dc66b8476b990cda1efe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-6910000000-745b390b8b1b329a9252	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-1e8e811f90230b3be376	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-3290000000-0b623b033726827aa22f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-7930000000-e7e194d99480b7e53401	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0190000000-690c257e3fce5319d7e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007k-1980000000-582b4105598dbfb055a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fka-2930000000-1497d0c7ca0d6bc1bb68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0090000000-6fdb2cf7255c1034e8fc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0390000000-03b23664f4176b9e5847	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-2920000000-9f01b67d39967a5a1203	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9620000000-7309f4ee3918ea05f00d	Spectrum

Toxicity Profile

Route of Exposure

Intravenous; oral; parenteral (intramuscular). The oral bioavailability of meperidine in patients with normal hepatic function is 50-60% due to extensive first-pass metabolism. Bioavailability increases to 80-90% in patients with hepatic impairment (e.g. liver cirrhosis). Meperidine is less than half as effective when administered orally compared to parenteral administration. One study reported that 80-85% of the drug administered intramuscularly was absorbed within 6 hours of intragluteal injection in health adults; however, inter-individual variation and patient-specific variable appear to cause considerable variations in absorption upon IM injection.

Mechanism of Toxicity

Meperidine is primarily a kappa-opiate receptor agonist and also has local anesthetic effects. Meperidine has more affinity for the kappa-receptor than morphine. 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 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.

Metabolism

Meperidine is metabolized in the liver by hydrolysis to meperidinic acid followed by partial conjugation with glucuronic acid. Meperidine also undergoes N-demethylation to normeperidine, which then undergoes hydrolysis and partial conjugation. Normeperidine is about half as potent as meperidine, but it has twice the CNS stimulation effects. Route of Elimination: Excreted in the urine. The proportion of drug that is excreted unchanged or as metabolites is dependent on pH. When urine pH is uncontrolled, 5-30% of the meperidine dose is excreted as normeperidine and approximately 5% is excreted unchanged. Meperidine and normeperidine are found in acidic urine, while the free and conjugated forms of meperidinic and normperidinic acids are found in alkaline urine. Half Life: Initial distribution phase (t_{1/2 α}) = 2-11 minutes; terminal elimination phase (t_{1/2 β}) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t_{1/2 β} is prolonged to 7-11 hours.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used to control moderate to severe pain.

Minimum Risk Level

Not Available

Health Effects

Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.

Symptoms

Not Available

Treatment

Primary attention should be given to the reestablishment of adequate respiratory exchange through provision of a patent airway and institution of assisted or controlled ventilation. The narcotic antagonist, naloxone hydrochloride, is a specific antidote against respiratory depression which may result from overdosage or unusual sensitivity to narcotics, including meperidine. Therefore, an appropriate dose of this antagonist should be administered, preferably by the intravenous route, simultaneously with efforts at respiratory resuscitation. An antagonist should not be administered in the absence of clinically significant respiratory or cardiovascular depression. Oxygen, intravenous fluids, vasopressors, and other supportive measures should be employed as indicated. In cases of overdosage with Meperidine tablets, the stomach should be evacuated by emesis or gastric lavage. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00454

HMDB ID

HMDB0014597

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID