Butorphanol
(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol
Molecular Identity
Butorphanol
(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol
PubChem CID: 5361092
Butorphanol is levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain. It has a role as an opioid analgesic, an antitussive, a mu-opioid receptor agonist and a kappa-opioid receptor agonist.
2D Structure
Properties
C21H29NO2
Molecular Formula
327.50
Molecular Weight
g/mol
327.2198
Exact Mass
Da
3.8
XLogP
Drug-like (Lipinski: < 5)
43.7
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
3
H-Bond Acceptors
492
Complexity
SMILES
Canonical SMILES
SMILES: C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)OIsomeric SMILES
SMILES: C1CC[C@]2([C@H]3CC4=C([C@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)OSynonyms(20)
butorphanolButorfanol(-)-butorphanol42408-82-2levo-BC-2627Butorphanolum(-)-17-(Cyclobutylmethyl)morphinan-3,14-diolMorphinan-3,14-diol, 17-(cyclobutylmethyl)-(-)-N-cyclobutylmethyl-3,14-dihydroxymorphinanQV897JC36DCHEBI:3242(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diolDTXSID1022714butorfanolo(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo(7.5.3.0^(1,10).0^(2,7))heptadeca-2(7),3,5-triene-4,10-diol
Data from PubChem (NCBI)
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