(1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol; (2R,3R)-2,3-dihydroxybutanedioic acid

• ChemBase ID: 131474
• Molecular Formular: C25H35NO8
• Molecular Mass: 477.5473
• Monoisotopic Mass: 477.23626709
• SMILES: c1cc2c(cc1O)[C@@]13CCCC[C@]1([C@H](C2)N(CC3)CC1CCC1)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.Oc1ccc2c(c1)[C@]13CCCC[C@]3([C@H](C2)N(CC1)CC1CCC1)O
• InChI: InChI=1S/C21H29NO2.C4H6O6/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15;5-1(3(7)8)2(6)4(9)10/h6-7,13,15,19,23-24H,1-5,8-12,14H2;1-2,5-6H,(H,7,8)(H,9,10)/t19-,20+,21-;1-,2-/m11/s1
• InChIKey: GMTYREVWZXJPLF-BTVKVFNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene-4,10-diol; (2R,3R)-2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: L(+)-tartaric acid; butorphanol
• Synonyms: L-N-Cyclobutylmethyl-3,14-dihydroxymorphinan (+)-tartrate salt; Butorphanol (+)-tartrate salt

Database IDs

• CAS Number: 58786-99-5
• EC Number: 261-443-5
• MDL Number: MFCD00214257
• PubChem SID: 24892126; 162225752
• PubChem CID: 5462346

CALCULATED PROPERTIES

• Acid pKa: 9.864343
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.16574237
• LogD (pH = 7.4): 0.8131535
• Log P: 2.8903294
• Molar Refractivity: 95.921 cm^3
• Polarizability: 37.629734 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: QC7795000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22
• Safety Statements: 22-26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule IV; psychotrope; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRK1(4986), OPRM1(4988)

Product Information

• Purity: ≥99%

DETAILS

Sigma Aldrich - B9156

Biochem/physiol Actions
κ/μ opioid receptor agonist.