Fentanyl citrate

Base Information

• Chemical Name: Fentanyl citrate
• CAS No.: 990-73-8
• Molecular Formula: C₆H₈O₇*C₂₂H₂₈N₂O
• Molecular Weight: 528.602
• Hs Code.: 2933330000
• European Community (EC) Number: 213-588-0
• UNII: MUN5LYG46H
• DSSTox Substance ID: DTXSID80243933
• Wikidata: Q27104201
• NCI Thesaurus Code: C47994
• RXCUI: 142436
• Pharos Ligand ID: 4ZQJCPWP7BNN
• ChEMBL ID: CHEMBL688
• Mol file: 990-73-8.mol

Synonyms:Duragesic;Durogesic;Fentanest;Fentanyl;Fentanyl Citrate;Fentora;Phentanyl;R 4263;R-4263;R4263;Sublimaze;Transmucosal Oral Fentanyl Citrate

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

Chemical Property of Fentanyl citrate

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 153-156 °C
• Boiling Point: 466.2 °C at 760 mmHg
• Flash Point: 185.8 °C
• PSA: 155.68000
• LogP: 2.82610
• Storage Temp.: 2-8°C
• Solubility.: Soluble in water, freely soluble in methanol, sparingly soluble in ethanol (96 per cent).
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 528.24716611
• Heavy Atom Count: 38
• Complexity: 618

Purity/Quality:

Safty Information:

• Pictogram(s): T+， T， F
• Hazard Codes: T+,T,F
• Statements: 26/27/28-42/43-39/23/24/25-23/24/25-11-36/37
• Safety Statements: 7-16-36/37-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Recent ClinicalTrials: Prehospital Analgesia INtervention Trial (PAIN)
• Recent EU Clinical Trials: Spinal fentanyl or epidural analgesia in the early first phase of induced labor
• Recent NIPH Clinical Trials: A Phase 3 Study of MR13A11A
• Uses: Fentanyl citrate can be used as an analgesic.
• Clinical Use: A fentanyl patch is available for the treatment of severe chronic pain. This dosage form delivers fentanyl transdermally and provides effective analgesia for periods of up to 72 hours. In 1999, fentanyl also became available in a lollipop dose form for absorption from the oral cavity. Fentanyl's short duration of action after parenteral dose is caused by redistribution rather than by metabolism or excretion. Repeated doses of fentanyl can result in accumulation and toxicities. Elderly patients usually are more sensitive to fentanyl and require lower doses. Opioids have a wide spectrum of P-glycoprotein (P-gp) activity, acting as both substrates and inhibitors, which might contribute to their varying CNS-related effects. Although fentanyl, sufentanil, and alfentanil did not behave as P-gp substrates, they inhibited the in vitro P-gp–mediated efflux of drugs known to be P-gp transported, such as digoxin, increasing their blood levels and the potential for important drug interactions by inhibition of P-gp efflux transporter.

Technology Process of Fentanyl citrate

There total 6 articles about Fentanyl citrate 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: 95.0%

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide (437-38-7) + citric acid (77-92-9,906507-37-7) → fentanyl citrate (1863-07-6,990-73-8)

Guidance literature:

In methanol; at 20 ℃; for 2h;

DOI:10.1371/journal.pone.0108250

Reference yield:

4-piperidone hydrochloride (41979-39-9) → fentanyl citrate (1863-07-6,990-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate / acetonitrile / 5 h / 80 °C

2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

4: methanol / 2 h / 20 °C

With sodium tris(acetoxy)borohydride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1371/journal.pone.0108250

Reference yield:

1-phenyl-2-bromoethane (103-63-9) → fentanyl citrate (1863-07-6,990-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate / acetonitrile / 5 h / 80 °C

2: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 2 h / 20 °C / Cooling with ice

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C

4: methanol / 2 h / 20 °C

With sodium tris(acetoxy)borohydride; caesium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1371/journal.pone.0108250

upstream raw materials:

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide

citric acid

4-piperidone hydrochloride

1-phenyl-2-bromoethane

Downstream raw materials:

N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]propanamide

Refernces

• 1、 -. "SUBSTITUTED 4-AMINO-PIPERIDINES". Page/Page column 20. . Retrieved 2010/02/17.