(1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one; (2R,3R)-2,3-dihydroxybutanedioic acid

• ChemBase ID: 153412
• Molecular Formular: C22H27NO9
• Molecular Mass: 449.45108
• Monoisotopic Mass: 449.16858145
• SMILES: CN1CC[C@]23c4c5ccc(c4O[C@H]2C(=O)CC[C@H]3[C@H]1C5)OC.[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.COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4CCC1=O)C
• InChI: InChI=1S/C18H21NO3.C4H6O6/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;5-1(3(7)8)2(6)4(9)10/h3,6,11-12,17H,4-5,7-9H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-,12+,17-,18-;1-,2-/m01/s1
• InChIKey: OJHZNMVJJKMFGX-BWCYBWMMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-one; (2R,3R)-2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: L(+)-tartaric acid; hydrocodone
• Synonyms: 4,5-Epoxy-3-methoxy-17-methyl-5α-morphinan-6-one (2R,3R)-2,3-dihydroxybutanedioate (1:1); Hydrocodone (+)-bitartrate salt

Database IDs

• CAS Number: 143-71-5
• EC Number: 205-608-1
• MDL Number: MFCD00078557
• PubChem SID: 162247551; 24895519
• PubChem CID: 5463977

CALCULATED PROPERTIES

• Acid pKa: 18.002748
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.998823
• LogD (pH = 7.4): 0.7307476
• Log P: 1.960304
• Molar Refractivity: 82.7447 cm^3
• Polarizability: 32.383915 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; H2O: soluble62 mg/mL

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Empirical Formula (Hill Notation): C18H21NO3 · C4H6O6

DETAILS

Sigma Aldrich - H4516

Biochem/physiol Actions
μ opioid receptor agonist; narcotic analgesic and antitussive.