(1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol; (2R,3R)-2,3-dihydroxybutanedioic acid

• ChemBase ID: 134384
• Molecular Formular: C23H31NO7
• Molecular Mass: 433.49474
• Monoisotopic Mass: 433.21005234
• SMILES: C=CCN1CC[C@]23CCCC[C@H]2[C@@H]1Cc1c3cc(cc1)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.C=CCN1CC[C@@]23[C@H]([C@@H]1Cc1c3cc(cc1)O)CCCC2
• InChI: InChI=1S/C19H25NO.C4H6O6/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19;5-1(3(7)8)2(6)4(9)10/h2,6-7,13,16,18,21H,1,3-5,8-12H2;1-2,5-6H,(H,7,8)(H,9,10)/t16-,18+,19+;1-,2-/m01/s1
• InChIKey: FWMLYVACGDQRFU-ZTMWJVNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10R)-17-(prop-2-en-1-yl)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol; (2R,3R)-2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: L(+)-tartaric acid; levallorphan
• Synonyms: 17-(2-Propenyl)morphinan-3-ol tartrate; Levallorphan tartrate salt

Database IDs

• CAS Number: 71-82-9
• EC Number: 200-767-3
• MDL Number: MFCD00210203
• PubChem SID: 162228660; 24278815
• PubChem CID: 5464111

CALCULATED PROPERTIES

• Acid pKa: 10.3627615
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.6962585
• LogD (pH = 7.4): 1.9874055
• Log P: 3.7553673
• Molar Refractivity: 87.2436 cm^3
• Polarizability: 33.84198 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: white solid
• Optical Rotation: [α]22/D -35°, c = 0.38 in H2O(lit.)

Safety Information

• RTECS: QD0480000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... OPRD1(4985), OPRM1(4988)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - L121

Biochem/physiol Actions
Partial agonist (antagonist) at μ and δ opioid receptors.
Caution
Photosensitive