Propoxyphene

Base Information

• Chemical Name: Propoxyphene
• CAS No.: 469-62-5
• Deprecated CAS: 21086-94-2,3818-94-8,3818-94-8
• Molecular Formula: C22H29 N O2
• Molecular Weight: 339.478
• European Community (EC) Number: 207-420-5
• UNII: II2G62OV6F,S2F83W92TK
• DSSTox Substance ID: DTXSID1023524
• Nikkaji Number: J5.928E
• Wikipedia: Dextropropoxyphene
• Wikidata: Q2268608
• NCI Thesaurus Code: C61912,C61711
• Pharos Ligand ID: VYH4RZ1YFVNF
• Metabolomics Workbench ID: 57642
• ChEMBL ID: CHEMBL1213351
• Mol file: 469-62-5.mol

Synonyms:D Propoxyphene;D-Propoxyphene;Darvon;Dextropropoxyphene;Hydrochloride, Propoxyphene;Propoxyphene;Propoxyphene Hydrochloride;Propoxyphene Hydrochloride, (R*,R*)-(+-)-Isomer;Propoxyphene Hydrochloride, (R-(R*,R*))-Isomer;Propoxyphene Hydrochloride, (R-(R*,S*))-Isomer;Propoxyphene Hydrochloride, (S-(R*,R*))-Isomer;Propoxyphene Maleate, (+)-Isomer;Propoxyphene Phosphate, (S-(R*,S*))-Isomer;Propoxyphene Sulfate, (S-(R*,S*))-Isomer

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Propoxyphene

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 165±3ºC
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 444 °C at 760 mmHg
• PKA: pKa 6.3(50% aq EtOH) (Uncertain)
• Flash Point: 130.6 °C
• PSA: 29.54000
• Density: 1.038 g/cm³
• LogP: 4.27550
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 339.219829168
• Heavy Atom Count: 25
• Complexity: 397

Purity/Quality:

Safty Information:

• Pictogram(s): F,Xn,T
• Hazard Codes: F,Xn,T
• Statements: 11-20/21/22-36-52/53-25
• Safety Statements: 16-26-36/37-61-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C
• Isomeric SMILES: CCC(=O)O[C@](CC1=CC=CC=C1)(C2=CC=CC=C2)[C@H](C)CN(C)C
• Uses: Analgesic.
• Biological Functions: Propoxyphene (dextropropoxyphene; Darvon) is structurally related to methadone but is much less potent as an analgesic. Compared with codeine, propoxyphene is approximately half as potent and is indicated for the treatment of mild pain. It is not antipyretic or antiinflammatory like aspirin and is less useful than aspirin in most cases of mild pain. Toxicity from propoxyphene, especially in combination with other sedatives, such as alcohol, has led to a decrease in its use. Death following ingestion of alcohol in combination with propoxyphene can occur rapidly (within 20 minutes to 1 hour). The drug is not indicated for those with histories of suicide or depressive illnesses. Like meperidine, propoxyphene has an active metabolite, norpropoxyphene, that is not analgesic but has excitatory and local anesthetic effects on the heart similar to those of quinidine. Use of the drug during pregnancy is not safe.Teratogenic effects have been observed in newborns, as have withdrawal signs at birth. As with morphine, propoxyphene requires adequate hepatic and renal clearance to prevent toxicity and drug accumulation. It is thus contraindicated in the elderly patient and those with renal or liver disease. Propoxyphene interacts with several drugs. The use of sedatives in combination with propoxyphene can be fatal. In addition, the metabolism of the drug is increased in smokers due to induction of liver enzymes. Thus, smokers may require a higher dose of the drug for pain relief. Propoxyphene enhances the effects of both warfarin and carbamazepine and may increase the toxicity associated with both drugs, such as bleeding and sedation, respectively.The abuse liability of propoxyphene is low because of the extreme irritation it causes at the site of injection. Oral use is the preferred route of administration for this reason.

Technology Process of Propoxyphene

There total 1 articles about Propoxyphene 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:

→ propoxyphene (469-62-5,21086-94-2,3818-94-8,8059-45-8)

Guidance literature:

Reference yield: 90.0%

propoxyphene (469-62-5,21086-94-2,3818-94-8,8059-45-8) + benzyl chloride (100-44-7) → (-)-N-benzylpropoxyphene chloride

Guidance literature:

In ethanol; for 18h; Heating;

DOI:10.1039/P19810000574

Reference yield:

propoxyphene (469-62-5,21086-94-2,3818-94-8,8059-45-8) → (S)-2,3-diphenyl-1-propanol (19643-66-4)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. H₂O₂ / methanol

2: 170 °C

3: O₃ / ethyl acetate

4: aq. HCl / ethanol

5: (i) Br₂, AcOH, (ii) Py, (iii) aq. NaOH

6: Ag₂O

7: H₂ / Raney-Ni / ethanol

8: LiAlH₄ / diethyl ether

With hydrogenchloride; lithium aluminium tetrahydride; hydrogen; dihydrogen peroxide; ozone; silver(l) oxide; nickel; In methanol; diethyl ether; ethanol; ethyl acetate;

DOI:10.1021/jo01044a056

Downstream raw materials:

(2S)-2,3-diphenyl-2-hydroxypropanoic acid

(S)-2,3-diphenyl-1-propanol

methyl (S)-(+)-2,3-diphenyl-2-hydroxypropionate

(S)-2,3-diphenyl-propionic acid methyl ester

Refernces

• 1、 -. "Synthesis and purification of d-propoxyphene hydrochloride". . . Retrieved 2008/06/13.