(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one hydrochloride

• ChemBase ID: 153483
• Molecular Formular: C20H24ClNO4
• Molecular Mass: 377.86186
• Monoisotopic Mass: 377.13938593
• SMILES: c1cc(c2c3c1C[C@@H]1[C@]4([C@]3(CCN1CC1CC1)[C@@H](O2)C(=O)CC4)O)O.Cl
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O.Cl
• InChI: InChI=1S/C20H23NO4.ClH/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11;/h3-4,11,15,18,22,24H,1-2,5-10H2;1H/t15-,18+,19+,20-;/m1./s1
• InChIKey: RHBRMCOKKKZVRY-ITLPAZOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-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 hydrochloride
• IUPAC Traditional name: naltrexone hydrochloride
• Synonyms: Naltrexone hydrochloride

Database IDs

• CAS Number: 16676-29-2
• EC Number: 240-723-0
• MDL Number: MFCD00069324
• Beilstein Number: 3580333
• PubChem SID: 162247622; 24278051
• PubChem CID: 5485201

CALCULATED PROPERTIES

• Acid pKa: 10.106068
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.4911842
• LogD (pH = 7.4): 0.13493212
• Log P: 1.3626752
• Molar Refractivity: 91.5015 cm^3
• Polarizability: 35.902298 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear, colorless

Safety Information

• RTECS: QD2160000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988), OPRS1(10280)

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C20H23NO4 · HCl

DETAILS

Sigma Aldrich - N3136

Biochem/physiol Actions
Competitive antagonist for μ, κ, δ, and σ-opioid receptors; has greater oral efficacy and longer duration of action than naloxone.

Sigma Aldrich - 70128

Other Notes
Narcotic antagonist.; Biphasic effect on the nicotinic acetylcholine receptor1