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
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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
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Subunit-specific mechanisms and proton sensitivity of NMDA receptor channel block.
J Physiol (Lond.), 581 (Pt 1): 107-28. [PMID:17303642]
2. Hanessian S, Parthasarathy S, Mauduit M, Payza K. (2003)
The power of visual imagery in drug design. Isopavines as a new class of morphinomimetics and their human opioid receptor binding activity.
J Med Chem, 46 (1): 34-48. [PMID:12502358]
3. Prommer E. (2007)
Levorphanol: the forgotten opioid.
Support Care Cancer, 15 (3): 259-64. [PMID:17039381]