Dezocine

Base Information

• Chemical Name: Dezocine
• CAS No.: 53648-55-8
• Molecular Formula: C₁₆H₂₃NO
• Molecular Weight: 245.365
• Hs Code.: 2922299014
• UNII: VHX8K5SV4X
• DSSTox Substance ID: DTXSID2022911
• Nikkaji Number: J10.888J
• Wikipedia: Dezocine
• Wikidata: Q1109018
• NCI Thesaurus Code: C65374
• Pharos Ligand ID: GX8599M2HY3A
• Metabolomics Workbench ID: 43423
• ChEMBL ID: CHEMBL1685
• Mol file: 53648-55-8.mol

Synonyms:(-5alpha, 11alpha,13s)-13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecen-3-ol;13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecenol;5,11-methanobenzocyclodecen-3-ol, 13-amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-, (5alpha,11alpha,13s*);dezocine;dezocine hydrobromide, (5alpha,11alpha,13*)-isomer;dezocine hydrobromide, (5alpha,11alpha,13S*)-isomer;dezocine hydrobromide, (5R-(5alpha,11alpha,13S*))-isomer;dezocine hydrobromide, (5S-(5alpha,11alpha,13*))-isomer;dezocine, (5alpha,11alpha,13S*)-isomer;Wy-16,225

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Chemical Property of Dezocine

Chemical Property:

• Vapor Pressure: 9.99E-07mmHg at 25°C
• Refractive Index: 1.568
• Boiling Point: 392.6 °C at 760 mmHg
• PKA: 10.06±0.40(Predicted)
• Flash Point: 191.3 °C
• PSA: 46.25000
• Density: 1.082 g/cm³
• LogP: 3.81390
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 245.177964357
• Heavy Atom Count: 18
• Complexity: 306

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCCCC(C1N)CC3=C2C=C(C=C3)O
• Isomeric SMILES: C[C@]12CCCCC[C@H]([C@@H]1N)CC3=C2C=C(C=C3)O
• Recent ClinicalTrials: The Efficacy and Safety of Dezocine Pretreatment for Pain Relief in Acne Scar Treatment of Fractional CO2 Laser
• Description: Dezocine is an injectable agonisthtagonist analgesic indicated when an opioid analgesic is suitable for the management of pain. The drug differs from other opioid agonisthtagonists by having a high affinity for both the mu and delta receptors and a low effect on kappa receptors. Dezocine is reported to have a rapid onset of action, short half-life and low abuse potential with insignificant side effects.
• Uses: Dezocine is an opioid analgesic that is related to Pentazocine (P274300). Dezocine is used to relieve post-operative pain with its potency comparable to Meperidine (M223900).
• Biological Functions: Dezocine (Dalgan) is a synthetic aminotetralin derivative with potent agonist–antagonist effects.The onset of activity and potency as an analgesic are comparable to those of morphine. Although the drug requires glucuronidation during metabolism, patients with hepatic insufficiency clear it normally.The main route for clearance is the kidney.Thus, patients with renal dysfunction are prone to buildup of dezocine over time. As an antagonist, dezocine is more potent than pentazocine. As an agonist, dezocine produces analgesia and respiratory depression (which is readily reversed by naloxone), but unlike pentazocine, it has little if any effect on the cardiovascular system. Dezocine is indicated as an analgesic for moderate to severe pain. In addition, it shows promise in chronic pain states, such as with victims of severe burns. Contraindications and adverse effects of the drug are similar to those described for morphine. No tendency toward abuse has been demonstrated thus far.
• Clinical Use: It is useful for the treatment of moderate to severe pain. It is available for intramuscular and intravenous dose. The drug is indicated for postoperative and cancerinduced pain.

Technology Process of Dezocine

There total 14 articles about Dezocine 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: 83.0%

(5R,11S,13S)-3-methoxy-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methylenebenzocyclodecene-13-amine (42264-11-9,48176-48-3,48176-49-4,50736-35-1,51017-49-3,58383-82-7,58406-56-7,58918-21-1,63230-09-1) → dezocine (52437-65-7,53648-55-8,58918-19-7,58957-67-8,83461-52-3)

Guidance literature:

With water; boron tribromide; In dichloromethane; for 12h;

DOI:10.1016/S0957-4166(00)86331-4

Reference yield:

dezocine hydrobromide (42013-66-1,42264-28-8,57236-36-9,58383-80-5,60505-64-8) → dezocine (52437-65-7,53648-55-8,58918-19-7,58957-67-8,83461-52-3)

Guidance literature:

With ammonium hydroxide; In water; for 0.25h; pH=9.5;

Reference yield:

(1R,9S)-4-Methoxy-1-methyl-tricyclo[7.5.1.02,7]pentadeca-2,4,6-trien-15-one oxime (42263-97-8,50666-38-1,131434-60-1) → dezocine (52437-65-7,53648-55-8,58918-19-7,58957-67-8,83461-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NH₄OH, H₂ / Raney-Ni W₇ / ethanol / 48 h / 50 °C / 3000.2 Torr

2: 83 percent / BBr₃, H₂O / CH₂Cl₂ / 12 h

With ammonium hydroxide; water; hydrogen; boron tribromide; Raney-Ni W₇; In ethanol; dichloromethane;

DOI:10.1016/S0957-4166(00)86331-4

upstream raw materials:

(5R,11S,13S)-3-methoxy-5-methyl-5,6,7,8,9,10,11,12-octahydro-5,11-methylenebenzocyclodecene-13-amine

(1R,9S)-4-Methoxy-1-methyl-tricyclo[7.5.1.0^2,7]pentadeca-2,4,6-trien-15-one oxime

(R)-(+)-7-methoxy-1-(5'-bromopentyl)-1-methyl-2-tetralone

1-methyl-7-methoxy-2-tetralone

Refernces

• 1、 -. "DEZOCINE ANALOGUE". Paragraph 0086; 0101; 0102. . Retrieved 2018/11/27.
• 2、 -. "Combination of selected opioids with muscarine antagonists for treating urinary incontinence". . . Retrieved 2008/06/13.