23327-57-3

Basic information

• Product Name: Nefopam hydrochloride
• Synonyms: BENZOXAZOCINE HYDROCHLORIDE;LABOTEST-BB LT00159839;ACUPAN;3-methyl-7-phenyl-6-oxa-3-azabicyclo[6.4.0]dodeca-8,10,12-triene hydrochloride;3,4,5,6-TETRAHYDRO-5-METHYL-1H-2,5-BENZOXAZOCINE HYDROCHLORIDE;3,4,5,6-TETRAHYDRO-5-METHYL-1-PHENYL-1H-2,5-BENZOXAZOCINE HYDROCHLORIDE;NEFOPAM HCL;NEFOPAM HYDROCHLORIDE
• CAS NO: 23327-57-3
• Molecular Formula: C₁₇H₁₉NO*ClH
• Molecular Weight: 289.8
• EINECS: 245-585-5
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;Other APIs
• Mol File: 23327-57-3.mol

Chemical Properties

• Melting Point: 238-242°
• Boiling Point: 369.5 °C at 760 mmHg
• Flash Point: 109 °C
• Appearance: white to beige/
• Density: 1.064g/cm3
• Vapor Pressure: 1.18E-05mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble5mg/mL, clear
• CAS DataBase Reference: Nefopam hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Nefopam hydrochloride(23327-57-3)
• EPA Substance Registry System: Nefopam hydrochloride(23327-57-3)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: 3249
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 23327-57-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Nefopam hydrochloride is used as a centrally acting skeletal muscle relaxant for the treatment of muscle spasms and pain. Its analgesic and antidepressant properties make it a valuable compound in the development of medications for various conditions.
Used in Research and Analysis:
Nefopam hydrochloride has been utilized as a standard for the quantitative determination of tramadol by gas chromatography-mass spectrometry (GC/MS), aiding in the accurate measurement and analysis of tramadol levels in various samples.

Biochem/physiol Actions

Nefopam is a centrally-acting analgesic drug of the benzoxazocine chemical class. Nefopam is a non-opioid, but has a potentiating effect on morphine and other opioids. Its mechanism of action is not certain, but may involve its action as a dopamine/serotonin/norepinephrine reuptake inhibitor.

Clinical Use

Analgesic for moderate pain

Drug interactions

Potentially hazardous interactions with other drugs Antidepressants: avoid MAOIs; tricyclics possibly increased risk of side effects.

Metabolism

Extensively metabolised in the liver to produce active metabolites. It is mainly excreted in the urine. About 8% of a dose is excreted via the faeces.

InChI:InChI=1/C17H19NO.ClH/c1-18-11-12-19-17(14-7-3-2-4-8-14)16-10-6-5-9-15(16)13-18;/h2-10,17H,11-13H2,1H3;1H

Upstream product

• 91463-82-0 (R)-5-methyl-1-phenyl-1,3,4,6-tetrahydro-2,5-benzoxazocine 
• 13669-70-0 nefopam 
• 85-52-9 2-Benzoylbenzoic acid 
• 22103-85-1 2-benzoylbenzoyl chloride 
• 24833-47-4 2-benzoyl-N-(2-hydroxyethyl)-N-methylbenzamide 
• 60725-36-2 2-[{2-[hydroxyl(phenyl)methyl]benzyl}(methyl)amino]ethanol 
• 27688-56-8 1-((2-(methylamino)methyl)phenyl)-1-phenylmethanol hydrochloride 
• 79-04-9 chloroacetyl chloride 
• 81616-14-0 tert-butyl N-benzyl-N-methylcarbamate 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 13669-70-0 nefopam 

Relevant articles and documents

Preparation method for nefopam hydrochloride

The invention discloses a preparation method for nefopam hydrochloride. The preparation method is characterized by comprising the following preparation steps: (A) performing a reaction on raw materials including tert-butyl N-benzyl-N-methyl carbamate and benzoyl chloride to obtain an intermediate tert-butyl N-(2-(benzoyl)benzyl)-N-methyl carbamate; (B) performing reduction on the intermediate tert-butyl N-(2-(benzoyl)benzyl)-N-methyl carbamate by a reductant, and performing acidolysis to obtain an intermediate 1-((2-(methylamino)methyl)phenyl)-1-phenylmethanol hydrochloride; and (C) performinga reaction on the intermediate 1-((2-(methylamino)methyl)phenyl)-1-phenylmethanol hydrochloride and chloroacetyl chloride to form an amide through a one-pot method, performing cyclization, and performing reduction by a reductant to obtain the objective compound nefopam hydrochloride. According to the invention, the reaction steps are simple, and the preparation method is easy to implement.

Old is Gold? Nefopam Hydrochloride, a Non-opioid and Non-steroidal Analgesic Drug and Its Practical One-Pot Synthesis in a Single Solvent for Large-Scale Production

Nefopam hydrochloride is extensively used in most of the European countries until today as an analgesic because of its non-opiate (non-narcotic) and non-steroidal action with fewer side effects compared with opioid and other analgesics, which cause more troublesome side effects. A multikilogram synthesis of nefopam hydrochloride has been achieved in one pot using a single solvent (toluene). A ≥99.9% purity of the active pharmaceutical ingredient (API) was achieved in excellent overall yield (≥79%). The one-pot, five-step synthetic process involves formation of an acid chloride (3) from benzoylbenzoic acid (2) followed by amidation (4), reduction (5), cyclization (6), and formation of the hydrochloride salt (1). The major advantages include (i) use of a single solvent, (ii) >90% conversion in each step, (iii) a cost-effective and operationally friendly process, (iv) averting the formation of genotoxic impurities, and (v) improved overall yield (≥79%) provided by the one-pot operation. For the first time, we report the characterization data of API 1, intermediates 3, 4, and 5, and also a possible impurity (5a).

RACEMISATION OF ENANTIOMERS OF NEFOPAM AND ANALOGUES

A process for the racemisation of a compound which is nefopam or an analogue thereof in the form of a single enantiomer or non-racemic mixture, which comprising contacting the compound with an acid.