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57-42-1 molecular structure
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ethyl 1-methyl-4-phenylpiperidine-4-carboxylate

ChemBase ID: 337
Molecular Formular: C15H21NO2
Molecular Mass: 247.33274
Monoisotopic Mass: 247.15722892
SMILES and InChIs

SMILES:
O(C(=O)C1(CCN(CC1)C)c1ccccc1)CC
Canonical SMILES:
CCOC(=O)C1(CCN(CC1)C)c1ccccc1
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

Cite this record

CBID:337 http://www.chembase.cn/molecule-337.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
IUPAC Traditional name
meperidine
Brand Name
Centralgin
Demarol
Demerol
Dispadol
Dolantin
Dolcontral
Dolosal
Dolsin
Isonipecaine
Lidol
Lydol
Meperidine Hcl
Meperidol
Methyl phenylpiperidine carbonic acid ethyl ester
Nemerol
Operidine
Petantin
Pethanol
Pethidin
Pethidine
Pethidineter
Petydyna
Phetidine
Piperosal
Pipersal
Piridosal
Synonyms
Meperidine
Meperidine solution
哌替啶 溶液
CAS Number
57-42-1
MDL Number
MFCD00057376
PubChem SID
24882043
160963800
46506899
PubChem CID
4058

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
610593 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -0.14636338  LogD (pH = 7.4) 1.627321 
Log P 2.4558003  Molar Refractivity 72.4837 cm3
Polarizability 28.46522 Å3 Polar Surface Area 29.54 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.9  LOG S -2.35 
Solubility (Water) 1.11e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3220 mg/L expand Show data source
Flash Point
11 °C expand Show data source
51.8 °F expand Show data source
Hydrophobicity(logP)
2.6 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
1230 expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
1 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-23/24/25-39/23/24/25 expand Show data source
Safety Statements
16-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H301 + H311 + H331-H370 expand Show data source
GHS Precautionary statements
P210-P260-P280-P301 + P310-P311 expand Show data source
RID/ADR
UN 1230 3/PG 2 expand Show data source
Drug Control
kontrollierte Droge in Deutschlandregulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)rat ... Oprm1(25601), Slc6a3(24898), Slc6a4(25553) expand Show data source
Concentration
1 mg/mL in methanol expand Show data source
Grade
drug standard expand Show data source
Empirical Formula (Hill Notation)
C15H21NO2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00454 external link
Item Information
Drug Groups approved
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. [PubChem]
Indication Used to control moderate to severe pain.
Pharmacology Meperidine is a synthetic opiate agonist belonging to the phenylpiperidine class. Meperidine may produce less smooth muscle spasm, constipation, and depression of the cough reflex than equivalent doses of morphine. The onset of action is lightly more rapid than with morphine, and the duration of action is slightly shorter. The chemical structure of meperidine is similar to local anesthetics. Meperidine is recommended for relief of moderate to severe acute pain and has the unique ability to interrupt postoperative shivering and shaking chills induced by amphotericin B. Meperidine has also been used for intravenous regional anesthesia, peripheral nerve blocks and intraarticular, epidural and spinal analgesia. Meperidine is considered a second-line agent for the treatment of acute pain.
Affected Organisms
Humans and other mammals
Biotransformation 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.
Absorption 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.
Half Life Initial distribution phase (t1/2 α) = 2-11 minutes; terminal elimination phase (t1/2 β) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t1/2 β is prolonged to 7-11 hours.
Protein Binding 60-80% bound to plasma proteins, primarily albumin and α1-acid glycoprotein. The presence of cirrhosis or active viral hepatitis does not appear to affect the extent of protein binding.
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.
Distribution Meperidine crosses the placenta and is distributed into breast milk.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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