Meptazinol hydrochloride

Base Information

• Chemical Name: Meptazinol hydrochloride
• CAS No.: 59263-76-2
• Molecular Formula: C15H23NO^.HCl
• Molecular Weight: 269.815
• Hs Code.: 2942000000
• European Community (EC) Number: 261-683-0
• UNII: T62FQ4ZCPA
• DSSTox Substance ID: DTXSID3045485
• Wikidata: Q27289714
• NCI Thesaurus Code: C87361
• ChEMBL ID: CHEMBL1477274
• Mol file: 59263-76-2.mol

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

Chemical Property of Meptazinol hydrochloride

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.6E-05mmHg at 25°C
• Melting Point: 250-252 °C
• Boiling Point: 354.8 °C at 760 mmHg
• Flash Point: 160.6 °C
• PSA: 23.47000
• LogP: 3.89560
• Storage Temp.: Desiccate at +4°C
• Solubility.: H2O: >10mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 269.1546421
• Heavy Atom Count: 18
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

Meptazinol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1(CCCCN(C1)C)C2=CC(=CC=C2)O.Cl
• Description: Meptazinol hydrochloride is an injectable narcotic analgesic with antagonist properties; it is similar in potency to meperidine. Meptazinol appears to have a low propensity toward respiratory depression and other opiate-like side effects, possibly due to selective interaction with the mu-1 receptor. Also somewhat unique for an analgesic, it interacts with central cholinergic receptors. An oral form of meptazinol is under development.
• Uses: Analgesic;Opiate receptor agonist Mixed opioid agonist-antagonist. Analgesic (narcotic)

Technology Process of Meptazinol hydrochloride

There total 9 articles about Meptazinol hydrochloride 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: 92.0%

3-ethylhexahydro-3-(3-methoxyphenyl)-1-methyl<1H>azepine (71556-73-5) → Meptazinol hydrochloride (59263-76-2)

Guidance literature:

With hydrogenchloride; for 48h; Heating;

Reference yield:

caprolactam (105-60-2,9012-16-2) → Meptazinol hydrochloride (59263-76-2)

Guidance literature:

Multi-step reaction with 7 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: 90 percent / aq. sodium hydroxide / Ambient temperature

5: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h

6: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating

7: 92 percent / 12 M hydrochloric acid / 48 h / Heating

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

Reference yield:

1-methyl-2-azepanone (2556-73-2) → Meptazinol hydrochloride (59263-76-2)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 88 percent / bromine / CH₂Cl₂ / 1 h / 30 °C

3: 90 percent / aq. sodium hydroxide / Ambient temperature

4: 1.) sodium amide / 1.) toluene, reflux, 2 h, 2.) THF, 2 h

5: 84 percent / lithium aluminium hydride / tetrahydrofuran / 2 h / Heating

6: 92 percent / 12 M hydrochloric acid / 48 h / Heating

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

upstream raw materials:

formaldehyd

3-(3-ethylhexahydro<1H>azepine-3-yl)phenol

3-ethylhexahydro-3-(3-methoxyphenyl)-1-methyl<1H>azepine

caprolactam

Downstream raw materials:

meptazinol 6-aminonicotinic acid carbamate benzyl ester

meptazinol 4-aminophenylacetic acid tert-butyl ester carbamate

C₃₁H₃₆N₂O₄

meptazinol benzylcarbamate tert-butyl ester

Refernces