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Meperidine Hydrochloride

HCID 5750
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
50-13-5
Standard SMILES
CCOC(=O)C1(c2ccccc2)CCN(C)CC1.Cl
InChIKey
WCNLCIJMFAJCPX-UHFFFAOYSA-N
Molecular formula
C15H22ClNO2
Average molar mass
283.79 g/mol
Monoisotopic mass
283.1339066

Overview

Pethidine hydrochloride is the hydrochloride salt of pethidine. An analgesic used for the treatment of postoperative and labour pain. It has a role as an opioid analgesic, an antispasmodic drug, a mu-opioid receptor agonist and a kappa-opioid receptor agonist. It contains a pethidine(1+).

Names & identifiers

Preferred name
Meperidine Hydrochloride
IUPAC
ethyl 1-methyl-4-phenylpiperidine-4-carboxylate;hydrochloride

Names & synonyms

MEPERIDINE HYDROCHLORIDEPethidine hydrochloride50-13-5AntiduolCentralginDispadolDolantalDolestineDolarenAlgilMeperidine HclAntidurol
Show more names
DoloneurinePetantinPiridosalDolenalDolenolMepadinPetidinDemerol hydrochloride

Database identifiers

CAS
50-13-5
PubChem CID
5750
DTXSID
DTXSID30950620
ChEMBL
CHEMBL1701
ChEBI
CHEBI:31984
UNII
N8E7F7Q170
EC Number
200-013-3

Properties

Computed structural properties

Topological polar surface area
29.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
19
Formal charge
0
Complexity
276

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Safety & regulation

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

GHS classification

GHS Classification · 4 items

Danger

H301 (98.6%): Toxic if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationMeperidine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 3 (98.6%)

Toxicology

Treatment · 1 item

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. (L1712)

Health Effects

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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<sub>1/2 &alpha;</sub>) = 2-11 minutes; terminal elimination phase (t<sub>1/2 &beta;</sub>) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t<sub>1/2 &beta;</sub> is prolonged to 7-11 hours.

FDA Pharmacological Classification · 2 items

MEPERIDINE HYDROCHLORIDE

Full Opioid Agonists [MoA]; Opioid Agonist [EPC]

MeSH Pharmacological Classification · 3 items

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage.

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS.

Uses & manufacturing

UsesUsed to control moderate to severe pain.

Related reactions

2 records
New reaction record
HRID 483798 reaction equation
HRID 483798As reactantuspto-grants-1993_07
HRID 2379036 reaction equation
HRID 2379036As reactantuspto-grants-1994_11

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.
Exposure Routes · 1 item

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.

Toxicity Summary · 1 item

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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Meperidine hydrochloride

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015