Meptazinol

Base Information

• Chemical Name: Meptazinol
• CAS No.: 54340-58-8
• Molecular Formula: C15H23NO
• Molecular Weight: 233.354
• Hs Code.: 2933990090
• European Community (EC) Number: 259-109-9
• UNII: 18Y7S5JKZD
• DSSTox Substance ID: DTXSID6048543
• Nikkaji Number: J12.372B
• Wikipedia: Meptazinol
• Wikidata: Q410618
• NCI Thesaurus Code: C87360
• Pharos Ligand ID: 4GWX5JTWBDBY
• Metabolomics Workbench ID: 154283
• ChEMBL ID: CHEMBL314437
• Mol file: 54340-58-8.mol

Synonyms:Meptazinol;Meptazinol Hydrochloride;Meptid;WY 22811;WY-22811;WY22811

Chemical Property of Meptazinol

Chemical Property:

• Vapor Pressure: 2.91E-05mmHg at 25°C
• Melting Point: 127-133 ºC
• Refractive Index: 1.523
• Boiling Point: 354.8 °C at 760 mmHg
• PKA: 9.95±0.10(Predicted)
• Flash Point: 160.6 °C
• PSA: 23.47000
• Density: 0.997g/cm³
• LogP: 3.09360
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 233.177964357
• Heavy Atom Count: 17
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

3-(3-ethyl-1-methylazepan-3-yl)phenol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1(CCCCN(C1)C)C2=CC(=CC=C2)O
• Uses: Analgesic.
• Therapeutic Function: Analgesic
• Clinical Use: Opioid analgesic used for moderate to severe pain
• Drug interactions: Potentially hazardous interactions with other drugsAntidepressants: possible CNS excitation or depression with MAOIs - avoid; possible CNS excitation or depression with moclobemide; possibly increased sedative effects with tricyclics. Antihistamines: increased sedative effects with sedating antihistamines. Antipsychotics: enhanced hypotensive and sedative effects. Dopaminergics: avoid with selegiline. Nalmefene: avoid concomitant use. Sodium oxybate: enhanced effect of sodium oxybate - avoid

Technology Process of Meptazinol

There total 7 articles about Meptazinol 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: 98.0%

Meptazinol hydrochloride (59263-76-2) → 3-(3-ethyl-1-methyl-1H-hexahydroazepin-3-yl)phenol (54340-58-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 15 - 35 ℃;

Reference yield: 90.0%

3-Ethyl-hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one (71556-74-6) → 3-(3-ethyl-1-methyl-1H-hexahydroazepin-3-yl)phenol (54340-58-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

Reference yield:

caprolactam (105-60-2,9012-16-2) → 3-(3-ethyl-1-methyl-1H-hexahydroazepin-3-yl)phenol (54340-58-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodamide / 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 30 min

2: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, 0 to -10 deg C, 10 min, 2.) THF, amb. temp., 1.5 h

3: 88 percent / bromine / CH₂Cl₂ / 1 h / 30 °C

4: 1.) butyl lithium, diisopropylamine / 1.) hexane/THF, reflux, 3 h, 2.) reflux, 3 h

5: 90 percent / lithium aluminium hydride / tetrahydrofuran / Heating

With lithium aluminium tetrahydride; n-butyllithium; bromine; sodium amide; diisopropylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

3-Ethyl-hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

caprolactam

1-methyl-2-azepanone

hexahydro-1-methyl-3-(3-oxocyclohexen-1-yl)<2H>azepin-2-one

Downstream raw materials:

meptazinol benzylcarbamate tert-butyl ester

meptazinol p-aminobenzoylcarbamate hydrochloride

meptazinol p-aminobenzoylcarbamate

meptazinol (PABA-PABA tert-butyl ester) carbamate

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF PRODRUGS OF OPIOIDS". Page/Page column 17. . Retrieved 2012/07/13.
• 2、 -. "Use of weak opioids and mixed opioid agonists/antagonists for treatment of urinary incontinence". . . Retrieved 2008/06/13.