ChemInform Abstract: BENZOXAZOCINE, EINE NEUE VERBINDUNGSKLASSE ZENTRAL WIRKSAMER SKELETTMUSKEL‐RELAXANTIEN

Klohs, M. W.; Draper, M. D.; Petracek, F. J.; Ginzel, K. H.; Re, O. N.

doi:10.1002/chin.197219312

Cited by 6 publications

(7 citation statements)

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“…In the first place, it was used as an antidepressant and as an antispasmodic drug due to its myorelaxant properties [10] but studies have shown its effectiveness in preventing acute postsurgical hyperalgesia [11] and modulation of non-surgical neuropathic pain [12]. It is a benzoxazocine known as 5-methyl-1-phenyl-1,3,4,6tetrahydro-2,5-benzoxazocine (C 17 H 19 NO) obtained from a non-sedative benzoxazocine and is a cyclized analogue of an antihistamine (diphenhydramine -C 17 H 21 NO) [13]. It has been demonstrated that Nefopam is unstable under acidic condition and can be easily oxidized [14].…”

Section: Pharmacological Propertiesmentioning

confidence: 99%

Nefopam and its Role in Modulating Acute and Chronic Pain

Ţigliş¹,

Neagu²,

Elfara³

et al. 2018

Rev. Chim.

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Pain is a very important issue to take into account during hospitalization. Nefopam, a centrally acting analgesic, has a relative safety pharmacological profile with few and well-tolerated side effects, being used to treat acute or chronic pain. It inhibits the central reuptake of serotonin, norepinephrine and dopamine and modulates the sodium and calcium channels having only few contraindications. Nefopam can be part of balanced analgesia along with others non-opioids agents in order to reduce the opioid consumption and their complications, to control postoperative pain and to reduce the risk of neuropathic pain appearance. In order to avoid its adverse reactions, a slow infusion is always recommended. Nefopam has its role in preventing the shivering appearance during neuraxial or general anesthesia, can modulate the emergence agitation after nasal and maxillofacial surgery and can inhibit the sever hiccup during mechanical ventilation. Some cases about fatal overdoses are reported in the literature.

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Section: Pharmacological Propertiesmentioning

confidence: 99%

Nefopam and its Role in Modulating Acute and Chronic Pain

Ţigliş¹,

Neagu²,

Elfara³

et al. 2018

Rev. Chim.

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“…Nefopam hydrochloride [5-methyl-1-phenyl-3,4,5,6-tetrahydro-1 H -2,5-benzoxazocine, ( 1 )] is a benzannelated eight-membered heterocyclic non-narcotic analgesic drug with antidepressant properties . X-ray crystallographic determination of the structures of (+)- , and (−) chiral crystals and of the racemic modification ,, of nefopam hydrochloride ( 1 ) showed the 2,5-benzoxazocine ring to be bent into the boat-boat conformation (BB).…”

Section: Introductionmentioning

confidence: 99%

Eight-Membered-Ring Solid-State Conformational Interconversion via the Atom-Flip Mechanism, a CPMAS¹³C NMR and Crystallographic Stereochemical Study

et al. 2000

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Nefopam methohalide (chloride, bromide, and iodide) medium-ring quaternary ammonium salts of the non-narcotic analgesic tertiary amine drug give crystals belonging to the identical monoclinic P2(1)/c space group, and all of these pseudopolymorphs exhibit the same packing motif. A singular boat-boat (BB) more compact conformation is observed in the nefopam methochloride crystal. Larger halide anions (bromide and iodide) increase the void distance between the 2(1)-screw axis related adjacent ammonium cations to accommodate void-size dependent equilibrium quantities of the twist-chair-chair (TCC) more extended conformation. The BB:TCC occupancy factors are 0.961(5):0.039(5) [193 K], 0.780(5):0.220(5) [293 K], and 0.755(6):0.245(6) [343 K] for the methobromide crystal, while values of 0.657(5):0.343(5) [193 K] and 0.592(7):0.408(7) [293 K] were measured for the methiodide. Above a minimum of ca. 2.53 A, the occupancy factors were found to be linearly correlated to the intermolecular (TCC)Me(eq)-H...H-Me(ax)(TCC) distance between abutting methyl group protons in 2(1)-screw axis related neighbors. Temperature-dependent occupancy factors for the two conformers are interpreted in terms of a medium ring atom-flip facile interconversion between the two low energy conformations in crystals containing the appropriate size intercation void. A BB/TCC atom-flip interconversion in the methochloride unit cell would result in van der Waals interactions due to an estimated 2.31 A close intermolecular (TCC)Me(eq)-H...H-Me(ax)(TCC) distance between adjacent 2(1)-screw symmetry ammonium cations. The 203 K low-temperature CPMAS 13C NMR spectrum of the methiodide salt showed two slow exchange limit (SEL) delta 57.91 [BB] and delta 63.10 [TCC] OCH2CH2N peaks. A variable low-temperature CPMAS NMR investigation of the solid methiodide showed complex dynamic behavior that cannot be interpreted solely on the basis of an atom-flip conformational interconversion. Local magnetic fields from the gem-dimethyl rapidly rotating proton magnetic dipoles provide a distance-dependent T1 relaxation mechanism for neighboring carbons in the solid-state.

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“…127 Benzoxazocines, such as nefopam hydrochloride, 128 are non-narcotic analgesic drugs with antidepressant properties. 129 Gallagher and coworkers reported nucleophilic cleavage of enantiomerically pure 1,2-cyclic sulfamidates (611, 630) with oxygen and nitrogen nucleophile (629), followed by Mitsunobu reaction of 631, which provided an entry to substituted benzoxazepines (632) and benzodiazepines (633). Application of this methodology to 1,3-cyclic sulfamidates affords parallel entry to the analogous substituted 1,5-benzoxazocines (634) and 1,5benzodiazocines (635) (Scheme 102).…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Amino acid chirons: a tool for asymmetric synthesis of heterocycles

et al. 2014

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As a result of their easy availability in enantiomerically enriched form and their possession of synthetically transformable diverse functional groups, amino acids have been extensively used by synthetic organic and medicinal chemists as a chiral pool for access to heterocycles (monocycles, bicycles or polycycles, either bridged or fused). This review describes the syntheses of diverse asymmetric heterocycles with various membered rings (n = 3-9) followed by benzo or heteroannulated ones, for the period from 1996 to Dec. 2013. It details solution phase synthetic methodologies in which the naturally occurring α-amino acid is incorporated, totally or partially, into the final product.

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ChemInform Abstract: BENZOXAZOCINE, EINE NEUE VERBINDUNGSKLASSE ZENTRAL WIRKSAMER SKELETTMUSKEL‐RELAXANTIEN

Cited by 6 publications

References 0 publications

Nefopam and its Role in Modulating Acute and Chronic Pain

Nefopam and its Role in Modulating Acute and Chronic Pain

Eight-Membered-Ring Solid-State Conformational Interconversion via the Atom-Flip Mechanism, a CPMAS¹³C NMR and Crystallographic Stereochemical Study

Amino acid chirons: a tool for asymmetric synthesis of heterocycles

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ChemInform Abstract: BENZOXAZOCINE, EINE NEUE VERBINDUNGSKLASSE ZENTRAL WIRKSAMER SKELETTMUSKEL‐RELAXANTIEN

Cited by 6 publications

References 0 publications

Nefopam and its Role in Modulating Acute and Chronic Pain

Nefopam and its Role in Modulating Acute and Chronic Pain

Eight-Membered-Ring Solid-State Conformational Interconversion via the Atom-Flip Mechanism, a CPMAS13C NMR and Crystallographic Stereochemical Study

Amino acid chirons: a tool for asymmetric synthesis of heterocycles

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Eight-Membered-Ring Solid-State Conformational Interconversion via the Atom-Flip Mechanism, a CPMAS¹³C NMR and Crystallographic Stereochemical Study