(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-11-ol hydrochloride

• ChemBase ID: 130669
• Molecular Formular: C29H42ClNO4
• Molecular Mass: 504.10108
• Monoisotopic Mass: 503.28023651
• SMILES: C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]1[C@]42CCN([C@H]3Cc2c4c(c(cc2)O)O1)CC1CC1)OC)(C(C)(C)C)O.Cl
• Canonical SMILES: CO[C@]12CC[C@]3(C[C@@H]1[C@@](C(C)(C)C)(O)C)[C@@]14[C@H]2Oc2c4c(C[C@@H]3N(CC1)CC1CC1)ccc2O.Cl
• InChI: InChI=1S/C29H41NO4.ClH/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28;/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3;1H/t20-,21-,24-,26+,27-,28+,29-;/m1./s1
• InChIKey: UAIXRPCCYXNJMQ-RZIPZOSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-11-ol hydrochloride
• IUPAC Traditional name: buprenorphine hydrochloride
• Synonyms: [5α,7α(S)]-17-(Cyclopropylmethyl)-α-(1,1-dimethylethyl)4,5-epoxy-18,19-dihydo-3-hydroxy-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanol hydrochloride; Buprenorphine hydrochloride; Buprenorphine hydrochloride solution; 丁丙诺啡 盐酸盐; 丁丙诺啡 盐酸盐 溶液

Database IDs

• CAS Number: 53152-21-9
• EC Number: 258-396-8; 200-659-6
• MDL Number: MFCD00084836
• PubChem SID: 24892130; 162224947; 24892004
• PubChem CID: 3033050

CALCULATED PROPERTIES

• Acid pKa: 10.415402
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.58735055
• LogD (pH = 7.4): 1.6101108
• Log P: 3.5498807
• Molar Refractivity: 131.7623 cm^3
• Polarizability: 52.271748 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 11 °C; 51.8 °F

Safety Information

• RTECS: KM7758000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1230
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 63-22-62
• Safety Statements: 26-36; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H301-H311-H331-H370; H302-H361
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P281
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1230 3/PG 2
• Drug Control: Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; USDEA Schedule III; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

Product Information

• Grade: analytical standard, for drug analysis

DETAILS

Sigma Aldrich - B9275

Biochem/physiol Actions
Full agonist at ORL1 receptors, antagonist or partial agonist at μ, κ, and δ opioid receptors.