Phenazocine

Base Information

• Chemical Name: Phenazocine
• CAS No.: 127-35-5
• Molecular Formula: C22H27NO
• Molecular Weight: 321.462
• Hs Code.: 2933399078
• European Community (EC) Number: 204-835-3
• DSSTox Substance ID: DTXSID90860736
• Nikkaji Number: J5.392I
• Wikipedia: Phenazocine
• Wikidata: Q110184326
• NCI Thesaurus Code: C96728
• Metabolomics Workbench ID: 136460
• ChEMBL ID: CHEMBL46399
• Mol file: 127-35-5.mol

Synonyms:Hydrobromide, Phenazocine;Narphen;Phenazocine;Phenazocine Hydrobromide;Phenbenzorphan;Phenethylazocine

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Chemical Property of Phenazocine

Chemical Property:

• Vapor Pressure: 4.05E-09mmHg at 25°C
• Refractive Index: 1.59
• Boiling Point: 461 °C at 760 mmHg
• PKA: pKa 8.50(50% aq EtOH) (Uncertain)
• Flash Point: 220.5 °C
• PSA: 23.47000
• Density: 1.097 g/cm³
• LogP: 4.09700
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 321.209264485
• Heavy Atom Count: 24
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC3=C(C1(CCN2CCC4=CC=CC=C4)C)C=C(C=C3)O
• Uses: Phenazocine is an opioid analgesic drug related to Pentazocine (P274300) and has a similar profile of effects. The use of Phenazocine results in analgesia and euphoria and in some cases dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors. Phenazocine is a much more potent analgesic than morphine with about 4 times the potency and very little side effects making it a better treatment option for biliary or pancreatic pain. Controlled Substance.
• Therapeutic Function: Narcotic analgesic

Technology Process of Phenazocine

There total 5 articles about Phenazocine 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: 59.0%

N-(2-phenylethyl)-2-(4-methoxybenzyl)-3,4-dimethyl-1,2,5,6-tetrahydropyridine (1100-37-4) → phenazocine (127-35-5)

Guidance literature:

With hydrogen bromide; In water; at 135 ℃; for 24h;

DOI:10.1080/00397910903531722

Reference yield:

→ phenazocine (127-35-5)

Guidance literature:

entspr. Pyridin (III), HBr, Δ;

Reference yield:

acetic anhydride (108-24-7) → (+/-)-6,11syn-dimethyl-3-phenethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benz[d]azocin-8-ol (127-35-5,56942-74-6,58073-76-0,58640-87-2,64023-93-4,100100-58-1)

Guidance literature:

Erwaermen des Reaktionsprodukts mit Bromcyan in Chloroform,Erhitzen Rueckstandes mit wss.Salzsaeure, Behandeln mit wss.Methanol, Kaliumcarbonat und Phenylacetylchlorid und Erwaermen mit LiAlH₄;

DOI:10.1021/jo01092a012

upstream raw materials:

acetic anhydride

N-(2-phenylethyl)-2-(4-methoxybenzyl)-3,4-dimethyl-1,2,5,6-tetrahydropyridine

(+)-3,6,11syn-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benz[d]azocin-8-ol

Refernces

• 1、 Singh, Kamal Nain,Singh, Pushpinder,Sharma, Arvind Kumar,Singh, Paramjit,Kessar, Satinder V.. "A Short synthesis of benzomorphane analgesics (±)-Metazocine and (±)-Phenazocine". experimental part. p. 3716 - 3720. Retrieved 2010/12/29.