(1S,9S,13S)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol

• ChemBase ID: 131240
• Molecular Formular: C19H27NO
• Molecular Mass: 285.42378
• Monoisotopic Mass: 285.20926449
• SMILES: C[C@@H]1[C@@H]2Cc3ccc(cc3[C@]1(CCN2CC=C(C)C)C)O
• Canonical SMILES: CC(=CCN1CC[C@]2([C@@H]([C@@H]1Cc1c2cc(cc1)O)C)C)C
• InChI: InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m1/s1
• InChIKey: VOKSWYLNZZRQPF-CCKFTAQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S,13S)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2,4,6-trien-4-ol
• IUPAC Traditional name: (1S,9S,13S)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2,4,6-trien-4-ol
• Synonyms: (-)-Pentazocine; (+)-Pentazocine

Database IDs

• CAS Number: 359-83-1; 7361-76-4
• EC Number: 206-634-6
• MDL Number: MFCD00869259
• PubChem SID: 162225518; 24898179
• PubChem CID: 12259685

CALCULATED PROPERTIES

• Acid pKa: 10.421619
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.8584462
• LogD (pH = 7.4): 1.9896134
• Log P: 3.89362
• Molar Refractivity: 89.7993 cm^3
• Polarizability: 34.580894 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white solid
• Optical Rotation: [α]23/D +134.6°, c = 1 in chloroform(lit.)

Safety Information

• Storage Condition: protect from light
• RTECS: PB8750000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22; 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302; H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule IV; Home Office Schedule 3; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: room temp

Pharmacology Properties

• Gene Information: human ... EBP(10682)rat ... Chrm1(25229), Chrm2(81645), Drd2(24318), Oprm1(25601)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - P127

Biochem/physiol Actions
σ receptor agonist; active enantiomer of pentazocine.
Caution
Photosensitive
Reconstitution
A 10 mM solution of (+)-pentazocine is prepared by warming 28.5 mg of (+)-pentazocine free base in 2 mL of 0.1N HCl with shaking or sonication. When all solids have dissolved, the solution is cooled to room temperature and diluted with 10 mL of pH 7 buffer. Solutions should be freshly prepared, since cooling below room temperature may result in precipitation.