(1R,9R)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol; (2S)-2-hydroxy-2-phenylacetic acid

• ChemBase ID: 154253
• Molecular Formular: C29H37NO4
• Molecular Mass: 463.60838
• Monoisotopic Mass: 463.27225867
• SMILES: c1ccc(cc1)[C@@H](C(=O)O)O.c1cc2c(cc1O)[C@@]13CCCCC1[C@@H](C2)N(CC3)CC1CCC1
• Canonical SMILES: OC(=O)[C@H](c1ccccc1)O.Oc1ccc2c(c1)[C@]13CCCCC3[C@@H](C2)N(CC1)CC1CCC1
• InChI: InChI=1S/C21H29NO.C8H8O3/c23-17-8-7-16-12-20-18-6-1-2-9-21(18,19(16)13-17)10-11-22(20)14-15-4-3-5-15;9-7(8(10)11)6-4-2-1-3-5-6/h7-8,13,15,18,20,23H,1-6,9-12,14H2;1-5,7,9H,(H,10,11)/t18?,20-,21-;7-/m10/s1
• InChIKey: CBWUCCIELNNDND-QADVRDRQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol; (2S)-2-hydroxy-2-phenylacetic acid
• IUPAC Traditional name: (1R,9R)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol; (S)-mandelic acid
• Synonyms: (-)-3-Hydroxy-N-cyclobutylmethylmorphinan S(+)-mandelate; MCL-101 Mandelate; Butorphan S(+)-mandelate

Database IDs

• PubChem SID: 162248392
• PubChem CID: 71311823

CALCULATED PROPERTIES

• Acid pKa: 10.011609
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0796643
• LogD (pH = 7.4): 1.4659201
• Log P: 3.5669806
• Molar Refractivity: 94.6239 cm^3
• Polarizability: 37.03205 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ~5 mg/mL
• Apperance: light yellow solid

Safety Information

• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H29NO · C8H8O3

DETAILS

Sigma Aldrich - B1935

Biochem/physiol Actions
κ/μ opioid receptor agonist.