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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: dextromethorphan

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (no history prior to 1982))
International Nonproprietary Names Click here for help
INN number INN
166 dextromethorphan
Synonyms Click here for help
d-methorphan
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-39703, R-ALL-9679830
Reactome Reaction Reactome logo R-HSA-76456, R-HSA-9679816
Other databases
CAS Registry No. 125-71-3
ChEMBL Ligand CHEMBL52440
DrugBank Ligand DB00514
DrugCentral Ligand 842
GtoPdb PubChem SID 178103535
PubChem CID 5360696
Search Google for chemical match using the InChIKey MKXZASYAUGDDCJ-NJAFHUGGSA-N
Search Google for chemicals with the same backbone MKXZASYAUGDDCJ
Search PubMed clinical trials dextromethorphan
Search PubMed titles dextromethorphan
Search PubMed titles/abstracts dextromethorphan
Search UniChem for chemical match using the InChIKey MKXZASYAUGDDCJ-NJAFHUGGSA-N
Search UniChem for chemicals with the same backbone MKXZASYAUGDDCJ
Wikipedia Dextromethorphan