Lofexidine hydrochloride

Base Information

• Chemical Name: Lofexidine hydrochloride
• CAS No.: 21498-08-8
• Molecular Formula: C11H12 Cl2 N2 O . Cl H
• Molecular Weight: 295.596
• Hs Code.: 2933290090
• European Community (EC) Number: 809-032-7
• NSC Number: 759654
• UNII: V47G1SDI1B
• DSSTox Substance ID: DTXSID0020781
• Wikidata: Q27291521
• NCI Thesaurus Code: C87581
• RXCUI: 235853
• Pharos Ligand ID: L6KYN67PB9Y8
• ChEMBL ID: CHEMBL1788132
• Mol file: 21498-08-8.mol

Synonyms:2-(alpha-(2,6-dichlorophenoxy)ethyl) delta-2-imidazoline;BritLofex;lofexidine;lofexidine hydrochloride;Lofexidine mono-hydrochloride;lofexidine monohydrochloride;lofexidine, (+-)-isomer;Lucemyra

Chemical Property of Lofexidine hydrochloride

Chemical Property:

• Vapor Pressure: 6.35E-07mmHg at 25°C
• Melting Point: 230-232°C
• Boiling Point: 421.5 °C at 760 mmHg
• Flash Point: 208.7 °C
• PSA: 33.62000
• Density: g/cm³
• LogP: 3.32880
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: soluble20mg/mL, clear
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 294.009346
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

99% ^*data from raw suppliers

Lofexidine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=NCCN1)OC2=C(C=CC=C2Cl)Cl.Cl
• Recent ClinicalTrials: Efficacy, Safety and Dose-Response Study Followed by Open-Label Study of Lofexidine Treatment of Opioid Withdrawal
• Recent EU Clinical Trials: ''A Phase III, multicenter, open-label study, to evaluate the efficacy and safety of different dosage regimens of 0.2 mg lofexidine hydrochloride (DIMATEX) in the treatment of withdrawal symptoms during opioid detoxification''
• Uses: a2-Adrenoceptor agonist related structurally to Clonidine. Used in treatment of opioid withdrawal symptoms; antihypertensive. α2-Adrenoceptor agonist related structurally to Clonidine. Used in treatment of opioid withdrawal symptoms; antihypertensive. Lofexidine hydrochloride is an α2-adrenergic receptor agonist (Kd = 7.6 nM for rat cerebral cortex membranes) that has transient antihypertensive effects. It is used in managing opioid withdrawal symptoms during detoxification from heroin and methadone.
• Therapeutic Function: Antihypertensive

Technology Process of Lofexidine hydrochloride

There total 5 articles about Lofexidine 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: 90.0%

lofexidine (73372-53-9,81447-78-1,81447-79-2,31036-80-3) → lofexidine hydrochloride (21498-08-8)

Guidance literature:

With hydrogenchloride; In diethyl ether; ethanol; at 20 ℃; Solvent;

Reference yield: 66.9%

(±)ethyl 2-(2,6-dichlorophenoxy)propionate (344559-34-8,86981-78-4) + ethylenediamine (107-15-3,85404-18-8) → lofexidine hydrochloride (21498-08-8)

Guidance literature:

(±)ethyl 2-(2,6-dichlorophenoxy)propionate; ethylenediamine; With aluminum isopropoxide; In toluene; at 10 - 105 ℃; Inert atmosphere;

With hydrogenchloride; In isopropyl alcohol; at 10 - 50 ℃; for 2.5h; Solvent; Temperature;

Reference yield:

2,6-Dichlorophenol (87-65-0) → lofexidine hydrochloride (21498-08-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate; 4-methyl-2-pentanone / 20 °C / Inert atmosphere

1.2: 5 h / 116 °C / Inert atmosphere

2.1: titanium(IV) isopropylate / toluene / 1 h / 20 °C / Inert atmosphere

2.2: 18 h / 110 °C / Inert atmosphere

3.1: hydrogenchloride / diethyl ether; ethanol / 20 °C

With titanium(IV) isopropylate; hydrogenchloride; potassium carbonate; 4-methyl-2-pentanone; In diethyl ether; ethanol; toluene;

upstream raw materials:

2-(2,6-dichlorophenoxy)-propionitrile

ethylenediamine

2,6-Dichlorophenol

lofexidine

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF LOFEXIDINE". Page/Page column 15-16. . Retrieved 2021/10/22.
• 2、 Betzing,Biedermann. "Chemistry of Lofexidine". . p. 916 - 918. Retrieved 2007/10/02.