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Normeperidine

PubChem CID
32414
Structure
Normeperidine_small.png
Normeperidine_3D_Structure.png
Molecular Formula
Synonyms
  • Ethyl 4-phenylpiperidine-4-carboxylate
  • Normeperidine
  • Norpethidine
  • 77-17-8
  • Nordolsin
Molecular Weight
233.31 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-18
Description
Pethidine-Intermediate-B, ethyl-4-phenylpiperidine-4-carboxylate is a DEA Schedule II controlled substance. Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence. It is a Opiates substance.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Normeperidine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 4-phenylpiperidine-4-carboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

QKHMFBKXTNQCTM-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCOC(=O)C1(CCNCC1)C2=CC=CC=C2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C14H19NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

77-17-8

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEMBL ID

2.3.6 DEA Code Number

9233 (DEA schedule II controlled substance)

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 PharmGKB ID

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • normeperidine
  • normeperidine carbonate (2:1)
  • normeperidine hydrochloride
  • normeperidine, 3H-labeled cpd
  • norpethidine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
233.31 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
233.141578849 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
233.141578849 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
38.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
17
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
253
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Kovats Retention Index

Standard non-polar
1749 , 1749 , 1738 , 1745 , 1740 , 1775.2 , 1771 , 1738 , 1745
Semi-standard non-polar
1738 , 1770.9

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 8
View All
NIST Number
352194
Library
Main library
Total Peaks
138
m/z Top Peak
57
m/z 2nd Highest
42
m/z 3rd Highest
56
Thumbnail
Thumbnail
2 of 8
View All
NIST Number
43478
Library
Replicate library
Total Peaks
79
m/z Top Peak
57
m/z 2nd Highest
42
m/z 3rd Highest
56
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 DEA Drug and Chemical Information

7.1.1 DEA Controlled Substances

Substance
Pethidine-Intermediate-B, ethyl-4-phenylpiperidine-4-carboxylate
DEA Controlled Substances Code Number
9233
Controlled Substances Act Schedule
Schedule II - Substances in the DEA Schedule II have a high potential for abuse which may lead to severe psychological or physical dependence.
Class
Opiates

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Cholinesterase Inhibitors
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)

8.2 Metabolism / Metabolites

Normeperidine is a known human metabolite of meperidine.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

8.3 Human Metabolite Information

8.3.1 Cellular Locations

Membrane

8.4 Transformations

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (97.4%)

9.2 Regulatory Information

DEA Controlled Substances
DEA schedule II controlled substance

9.3 Other Safety Information

Chemical Assessment

IMAP assessments - 4-Piperidinecarboxylic acid, 4-phenyl-, ethyl ester: Environment tier I assessment

IMAP assessments - 4-Piperidinecarboxylic acid, 4-phenyl-, ethyl ester: Human health tier I assessment

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 ChemIDplus

15.3 ChEMBL Target Tree

15.4 UN GHS Classification

15.5 Drug Enforcement Administration (DEA) Classification

15.6 NORMAN Suspect List Exchange Classification

15.7 EPA DSSTox Classification

15.8 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    4-Piperidinecarboxylic acid, 4-phenyl-, ethyl ester
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  8. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  9. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  10. Drug Enforcement Administration (DEA)
    LICENSE
    Unless otherwise indicated, information on Department of Justice websites is in the public domain and may be copied and distributed without permission. Citation of the Department of Justice as source of the information is appreciated, as appropriate.
    https://www.justice.gov/legalpolicies
    Pethidine-Intermediate-B, ethyl-4-phenylpiperidine-4-carboxylate
    https://www.deadiversion.usdoj.gov/schedules/
    DEA drug and chemical classification
    https://www.dea.gov/drug-information/drug-scheduling
  11. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  14. Metabolomics Workbench
  15. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    4-Piperidinecarboxylic acid, 4-phenyl-, ethyl ester
    http://www.nist.gov/srd/nist1a.cfm
  16. SpectraBase
  17. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    normeperidine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  18. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  19. Springer Nature
  20. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  21. Wikidata
  22. Wikipedia
  23. PubChem
  24. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  25. GHS Classification (UNECE)
  26. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  27. PATENTSCOPE (WIPO)
  28. NCBI
CONTENTS