levorphanol   Click here for help

GtoPdb Ligand ID: 7595

Synonyms: (-) 3-hydroxy-N-methylmorphinan | Levo-Dromoran® | levorphanol hydrochloride | levorphanol tartrate
Approved drug
levorphanol is an approved drug (FDA (1953))
Compound class: Synthetic organic
Comment: Levorphanol is an opioid analgesic. Chemically it is the levorotatory optical isomer of racemorphan (PubChem CID 3918).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 23.47
Molecular weight 257.18
XLogP 3.29
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Oc1ccc2c(c1)C13CCCCC3C(C2)N(CC1)C
Isomeric SMILES Oc1ccc2c(c1)[C@]13CCCC[C@H]3[C@@H](C2)N(CC1)C
InChI InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
InChI Key JAQUASYNZVUNQP-USXIJHARSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
μ receptor Primary target of this compound Hs Agonist Agonist 9.9 pIC50 - 2
pIC50 9.9 (IC50 1.3x10-10 M) [2]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
GluN2C Hs Channel blocker - 6.2 pIC50 - 1
pIC50 6.2 (IC50 6.01x10-7 M) [1]
Description: Measured vs. exogenously expressed zeta1/epsilon3 (GRIN1/GRIN2C) subunits, at pH 6.9