dextromethorphan   Click here for help

GtoPdb Ligand ID: 6953

Synonyms: d-methorphan
Approved drug
dextromethorphan is an approved drug (FDA (no history prior to 1982))
Compound class: Synthetic organic
Comment: Dextromethorphan is a morphinan class sedative. It is available over-the-counter (OTC) for use as an antitussive. At doses much higher than medically recommended, dextromethorphan is used recreationally for its dissociative anesthetic and euphoria producing effects.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: dextromethorphan

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 12.47
Molecular weight 271.19
XLogP 3.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
Isomeric SMILES COc1ccc2c(c1)[C@@]13CCCC[C@@H]3[C@H](C2)N(CC1)C
InChI InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1
InChI Key MKXZASYAUGDDCJ-NJAFHUGGSA-N
References
1. Dravid SM, Erreger K, Yuan H, Nicholson K, Le P, Lyuboslavsky P, Almonte A, Murray E, Mosely C, Barber J et al.. (2007)
Subunit-specific mechanisms and proton sensitivity of NMDA receptor channel block.
J Physiol (Lond.), 581 (Pt 1): 107-28. [PMID:17303642]
2. Ganapathy ME, Prasad PD, Huang W, Seth P, Leibach FH, Ganapathy V. (1999)
Molecular and ligand-binding characterization of the sigma-receptor in the Jurkat human T lymphocyte cell line.
J Pharmacol Exp Ther, 289 (1): 251-60. [PMID:10087012]
3. Kotzer CJ, Hay DW, Dondio G, Giardina G, Petrillo P, Underwood DC. (2000)
The antitussive activity of delta-opioid receptor stimulation in guinea pigs.
J Pharmacol Exp Ther, 292 (2): 803-9. [PMID:10640321]
4. Meyerhof W, Batram C, Kuhn C, Brockhoff A, Chudoba E, Bufe B, Appendino G, Behrens M. (2010)
The molecular receptive ranges of human TAS2R bitter taste receptors.
Chem Senses, 35 (2): 157-70. [PMID:20022913]