d-Naloxone

Base Information

• Chemical Name: d-Naloxone
• CAS No.: 65700-73-4
• Molecular Formula: C19H21NO4
• Molecular Weight: 327.38
• UNII: 54MPN7YN98
• DSSTox Substance ID: DTXSID401029677
• Wikipedia: (+)-Naloxone
• Wikidata: Q4540629
• Metabolomics Workbench ID: 130878
• ChEMBL ID: CHEMBL3249799
• Mol file: 65700-73-4.mol

Synonyms:d-Naloxone;(+)-naloxone;54MPN7YN98;CHEMBL3249799;65700-73-4;Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5beta,9alpha,13alpha,14alpha)-;Naloxone, (+)-;UNII-54MPN7YN98;SCHEMBL12233786;DTXSID401029677;BDBM50497042;PDSP2_001521;Q4540629;(1R,5S,13S,17R)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0{1,13}.0{5,17}.0{7,18}]octadeca-7,9,11(18)-trien-14-one;(5beta,9alpha,13alpha,14alpha)-4,5-Epoxy-3,14-dihydroxy-17-(2-propen-1-yl)morphinan-6-one;Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propen-1-yl)-, (5beta,9alpha,13alpha,14alpha)-

Chemical Property of d-Naloxone

Chemical Property:

• Boiling Point: 532.8±50.0 °C(Predicted)
• PSA: 70.00000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 1.23930
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 327.14705815
• Heavy Atom Count: 24
• Complexity: 594

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
• Isomeric SMILES: C=CCN1CC[C@@]23[C@H]4C(=O)CC[C@@]2([C@@H]1CC5=C3C(=C(C=C5)O)O4)O

Technology Process of d-Naloxone

There total 9 articles about d-Naloxone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ naltrexone hydrochloride (465-65-6,65700-73-4,137170-88-8)

Guidance literature:

14-Hydroxydihydromorphinon,Allylbromid;

Reference yield:

ent-4,5α-epoxy-3,6-dimethoxy-17-methyl-morphina-6,8(14)-diene (23979-17-1) → (+)-Naloxone (65700-73-4)

Guidance literature:

Multi-step reaction with 7 steps

1: aq. H₂O₂ / formic acid; H₂SO₄ / 6.5 h

2: H₂ / Pd-BaSO₄ / acetic acid

3: BBr₃ / CHCl₃ / 0.83 h / 10 - 20 °C

4: 1 h / 100 °C

5: CHCl₃ / 32 h / Heating

6: aq. H₂SO₄ / 4.5 h / Heating

7: K₂CO₃ / dimethylformamide / 3 h / (heating)

With sulfuric acid; hydrogen; dihydrogen peroxide; boron tribromide; potassium carbonate; palladium on barium sulfate; In formic acid; chloroform; sulfuric acid; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jm00202a018

Reference yield:

ent-7ξ-bromo-4,5α-epoxy-3,6,6-trimethoxy-17-methyl-morphinane (65165-97-1) → (+)-Naloxone (65700-73-4)

Guidance literature:

Multi-step reaction with 8 steps

1: KOtBu / dimethylsulfoxide / 1.5 h / 80 - 90 °C

2: aq. H₂O₂ / formic acid; H₂SO₄ / 6.5 h

3: H₂ / Pd-BaSO₄ / acetic acid

4: BBr₃ / CHCl₃ / 0.83 h / 10 - 20 °C

5: 1 h / 100 °C

6: CHCl₃ / 32 h / Heating

7: aq. H₂SO₄ / 4.5 h / Heating

8: K₂CO₃ / dimethylformamide / 3 h / (heating)

With sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; boron tribromide; potassium carbonate; palladium on barium sulfate; In formic acid; chloroform; sulfuric acid; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm00202a018

upstream raw materials:

(+)-N-noroxymorphone

allyl bromide

ent-4,5α-epoxy-3,6-dimethoxy-17-methyl-morphina-6,8(14)-diene

ent-7ξ-bromo-4,5α-epoxy-3,6,6-trimethoxy-17-methyl-morphinane

Downstream raw materials:

6β-naloxol

6α-naloxol

C₁₉H₂₂N₂O₄

Refernces

• 1、 -. "N-dealkylation of N-alkyl-14-hydroxymorphinans and derivatives thereof". . . Retrieved 2008/06/13.