Compound: butorphanol
SMILES: Oc1cc2c(C[C@H]3N(CC4CCC4)CC[C@]25[C@@]3(O)CCCC5)cc1
InChIKey: IFKLAQQSCNILHL-QHAWAJNXSA-N
Synonyms: butorphanol, Butorfanol, (-)-butorphanol, 42408-82-2, levo-BC-2627, Butorphanolum, (-)-17-(Cyclobutylmethyl)morphinan-3,14-diol, Morphinan-3,14-diol, 17-(cyclobutylmethyl)-, (-)-N-cyclobutylmethyl-3,14-dihydroxymorphinan, QV897JC36D, CHEBI:3242, DTXSID1022714, (1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol, butorfanolo, (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, (1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo(7.5.3.01,10.02,7)heptadeca-2(7),3,5-triene-4,10-diol, (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, BC 2627, RefChem:56687, DTXCID502714, N02AF01, BC2627, 255-808-8, Butorphanol (free base), Butorfanol [INN-Spanish], Butorphanolum [INN-Latin], CHEMBL33986, l-BC 2627, DEA No. 9720, EINECS 255-808-8, Butorphanol (USAN/INN), UNII-QV897JC36D, Butorphanol [USAN:INN:BAN], BUTORPHANOL [MI], BUTORPHANOL [INN], BUTORPHANOL [USAN], BUTORPHANOL [VANDF], SCHEMBL3749, BUTORPHANOL [WHO-DD], BIDD:GT0549, GTPL7591, SCHEMBL29359664, BDBM50240437, N-cyclobutylmethyl-3,14-dihydroxymorphinan, DB-326245, NS00010339, L-N-Cyclobutylmethyl-3,14-dihydroxymorphinan, C06863, D03197, D-N-CYCLOBUTYLMETHYL-3,14-DIHYDROXYMORPHINAN, Q1185089, BRD-K42417338-045-01-9, 58115-67-6
Theoretical properties:
molecular_formula: C21H29NO2
molecular_weight: 327.5 g/mol
exact_mass: 327.219829168 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 24
topological_polar_surface_area: 43.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 272-274
solubility: Moderate
Descriptions:
pubchem: 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.
chebi: Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the <em>N</em>-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (<em>S</em>,<em>S</em>)-tartaric acid salt for relief or moderate to severe pain.
chembl: BUTORPHANOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and intranasal spray formulations. The tablet form is only used in dogs, cats and horses due to low bioavailability in humans.
It was patented in 1971 and approved for medical use in 1979.