(1S,5R,13R,14S)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraene-10,14-diol hydrochloride

• ChemBase ID: 132239
• Molecular Formular: C19H22ClNO3
• Molecular Mass: 347.83588
• Monoisotopic Mass: 347.12882125
• SMILES: C=CCN1CC[C@]23c4c5ccc(c4O[C@H]2[C@H](C=CC3[C@@H]1C5)O)O.Cl
• Canonical SMILES: C=CCN1CC[C@@]23C4[C@@H]1Cc1c3c(O[C@H]2[C@H](C=C4)O)c(cc1)O.Cl
• InChI: InChI=1S/C19H21NO3.ClH/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20;/h2-6,12-13,15,18,21-22H,1,7-10H2;1H/t12?,13-,15+,18+,19+;/m1./s1
• InChIKey: NAHATSPWSULUAA-HWXFZQNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraene-10,14-diol hydrochloride
• IUPAC Traditional name: (1S,5R,13R,14S)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraene-10,14-diol hydrochloride
• Synonyms: Nalorphine hydrochloride; N-烯丙基去甲吗啡盐酸盐; 纳洛芬盐酸盐; 烯丙吗啡 盐酸盐

Database IDs

• CAS Number: 57-29-4
• EC Number: 200-321-8
• MDL Number: MFCD00055164
• PubChem SID: 162226516; 24897450
• PubChem CID: 45260609

CALCULATED PROPERTIES

• Acid pKa: 10.204004
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.1795136
• LogD (pH = 7.4): 0.48296607
• Log P: 1.6752604
• Molar Refractivity: 89.2851 cm^3
• Polarizability: 34.137146 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dilute aqueous acid: soluble; ethanol: soluble; H2O: slightly soluble
• Apperance: white solid

Safety Information

• RTECS: QC7710000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Drug Control: USDEA Schedule III; regulated under CDSA - not available from Sigma-Aldrich Canada

DETAILS

Sigma Aldrich - N100

Caution
Photosensitive;
Biochem/physiol Actions
Mixed action opiate that is a partial agonist at μ and κ opioid receptors, and a low-affinity agonist at sigma receptors.

Sigma Aldrich - N3135

Biochem/physiol Actions
μ 受体拮抗剂、κ 受体部分激动剂和 σ 受体激动剂，但是与 σ 受体的亲和力不高