Tapentadol hydrochloride

Base Information

• Chemical Name: Tapentadol hydrochloride
• CAS No.: 175591-09-0
• Molecular Formula: C₁₄H₂₃NO*ClH
• Molecular Weight: 257.804
• European Community (EC) Number: 687-970-4
• UNII: 71204KII53
• DSSTox Substance ID: DTXSID00938677
• Wikidata: Q27265914
• NCI Thesaurus Code: C68922
• RXCUI: 857492
• ChEMBL ID: CHEMBL1201777
• Mol file: 175591-09-0.mol

Synonyms:3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)phenol;Nucynta;tapentadol;tapentadol hydrochloride

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Chemical Property of Tapentadol hydrochloride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 178-194°C
• Refractive Index: 1.518
• Boiling Point: 323.493°C at 760 mmHg
• Flash Point: 134.18°C
• PSA: 23.47000
• Density: 0.97g/cm³
• LogP: 3.88550
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 257.1546421
• Heavy Atom Count: 17
• Complexity: 193

Purity/Quality:

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1=CC(=CC=C1)O)C(C)CN(C)C.Cl
• Isomeric SMILES: CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C.Cl
• Recent ClinicalTrials: Comparison of Postoperative Analgesia Between Intravenous Paracetamol and Intranasal Tapentadol
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled, cross-over trial in healthy subjects to investigate the effects of lacosamide, pregabalin and tapentadol on biomarkers of pain processing observed by functional magnetic resonance imaging (FMRI) of the brain
• Description: Agonism of the MOR is a common strategy for moderate to severe pain intervention. Opioid drugs, such as morphine, that modulate this receptor have demonstrated efficacy in acute situations; however, chronic conditions, particularly those of neuropathic or inflammatory etiology, suffer from inadequate pain management with this treatment. With a narrow therapeutic window, traditional MOR agonists flirt with side effects at optimal analgesia, and prolonged use increases the potential for physical dependency. Since extensive efforts to design activators of MOR have failed to dissociate the undesirable adverse effects from the analgesic properties, the focus has been on enhancing the analgesic efficacy through a dual mechanism of action. Tapentadol hydrochloride brings this concept to fruition; MOR agonism is coupled with noradrenaline reuptake inhibition in a combinatory contribution to analgesia. Compared to morphine, it is about 50-fold less potent for MOR (Ki = 100 nM for tapentadol versus 2 nM for morphine). The Ki for inhibition of noradrenaline reuptake was 500 nM while reuptake of serotonin was only weakly inhibited (Ki = 2.5μM). Despite its lower affinity for MOR, the dual mechanism has provided an efficacious profile in both acute and chronic conditions with fewer side effects.
• Uses: A novel, centrally acting oral analgesic with a dual mode of action that has demonstrated efficacy in preclinical and clinical models of pain relief.
• Clinical Use: Tapentadol was approved by the FDA in November 2008 for the treatment of moderate to severe acute pain. It is a centrally acting analgesic that acts as both an agonist at the l-opiod receptor and as a norepinephrine re-uptake inhibitor, allowing it to have efficacy similar to potent narcotic analgesics but without their side effects. The drug was developed by Grunenthal and Johnson & Johnson and was marketed starting in 2009.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: possible opioid withdrawal with buprenorphine and pentazocine. Antidepressants: possible CNS excitation or depression with MAOIs - avoid concomitant use, and for 2 weeks after stopping MAOI; possible CNS excitation or depression with moclobemide; 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 concomitant use.

Technology Process of Tapentadol hydrochloride

There total 234 articles about Tapentadol 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: 100.0%

tapentadol (175591-23-8) → 3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol hydrochloride (175591-09-0)

Guidance literature:

With 2-methyltetrahydrofuran; hydrogenchloride; In water; at 29 ℃; Reagent/catalyst; Solvent; Reflux; Inert atmosphere;

Reference yield: 100.0%

tapentadol (175591-23-8) → tapentadol hydrochloride (175591-09-0)

Guidance literature:

With hydrogenchloride; In diethyl ether; for 4h;

Reference yield: 98.0%

(2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentane-1-amine hydrochloride → tapentadol hydrochloride (175591-09-0)

Guidance literature:

(2R,3R)-3-(3-methoxyphenyl)-N,N,2-trimethylpentane-1-amine hydrochloride; With hydrogen bromide; In water; for 2h; Reflux;

With sodium hydrogencarbonate; In water; pH=8 - 8.5;

With hydrogenchloride; In butanone;

upstream raw materials:

tapentadol

(-)-(2S,3S)-1-dimethylamino-3-(3-methoxy-phenyl)-2-methyl-pentan-3-ol hydrochloride

3'-nitropropiophenone

3-dimethylamino-2-methyl-1-(m-nitrophenyl)-1-propanone

Downstream raw materials:

tapentadol

Refernces

• 1、 -. "A synthetic hydrochloric acid he spurts he number of method". Paragraph 0104; 0105. . Retrieved 2017/08/25.
• 2、 -. "A he spurts him number of synthetic method". Paragraph 0046. . Retrieved 2017/03/08.