lidocaine

acetamide, 2- (diethylamino)-N-(2,6-dimethylphenyl)-

CAS: 137-58-6 C14 H22 N2 O MW: 234.34254000

Identification

Namelidocaine
IUPAC2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
CAS Number137-58-6
EINECS205-302-8
FDA UNII98PI200987
Molecular FormulaC14 H22 N2 O
Molecular Weight234.34254000
MDL NumberMFCD00026733
Nikkaji NumberJ5.631F
Beilstein2215784
XlogP32.30 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 68.50 °C. @ 760.00 mm Hg
Boiling Point 350.82 °C. @ 760.00 mm Hg (est)
Flash Point 331.00 °F. TCC ( 166.00 °C. ) (est)
logP (o/w) 2.440
Soluble in water, 4100 mg/L @ 30 °C (exp)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-child TDLo 21 mg/kg
Dermal Toxicitysubcutaneous-guinea pig LD50 120 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD\nVASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nLUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION', 'VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nBEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD', 'BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD\nVASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION\nLUNGS, THORAX, OR RESPIRATION: OTHER CHANGES']

Safety in Use

Categorypharmaceuticals / chemical synthisis
Recommendation for lidocaine usage levels up tonot for fragrance use.
Recommendation for lidocaine flavor usage levels up tonot for flavor use.

American International Chemical, Inc.

Consistent sources

North American supplier for globally sourced ingredients.

View All Website (800) 238-0001 info@aicma.com

BOC Sciences

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Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...

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Glentham Life Sciences Ltd

The Chemical, Biochemical & Research Essentials Supplier

Glentham Life Sciences is a supplier of fine chemicals and raw materials with warehousing, laboratories and packaging facilities in the UK.

View All Website +44 (0) 1225 667798 info@glentham.com

Penta International Corporation

Chemistry innovation

At Penta, our products and services help businesses do business better.

View All Website (973) 740-2300 lisaa@pentamfg.com

Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

acetamide, 2- (diethylamino)-N-(2,6-dimethylphenyl)- acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- 2',6'- acetoxylidide, 2-(diethylamino)- after burn spray alphacaine anestacon anestacon jelly cappicaine cito optadren dentipatch dermaflex a- diethylamino-2, 6-dimethylacetanilide a- diethylamino-2,6-dimethylacetanilide 2- diethylamino-2',6'-acetoxylidide a-( diethylamino)-2,6-acetoxylidide 2-( diethylamino)-2',6'-acetoxylidide 2-( diethylamino)-N-(2,6-dimethylphenyl)acetamide dilocaine N-(2,6- dimethylphenyl)-N2,N2-diethylglycinamide duncaine esracaine gravocain isicaina isicaine lanabiotic leostesin lida-mantle lidocaina lidocainum lidoderm lidoject-1 lidoject-2 lidothesin lignocaine lignocainum lignostab maricaine norwood sunburn spray octocaine octocaine-100 octocaine-50 oraqix rucaina solcain xilina xllina xycaine xylestesin xylocain xylocaine xylocitin xylotox zilactin-L PubMed: More methemoglobin is produced by benzocaine treatment than lidocaine treatment in human in vitro systems. PubMed: Convulsions during cataract surgery under peribulbar anesthesia: a case report. PubMed: Co-administration of memantine with epinephrine produces a marked peripheral action in intensifying and prolonging analgesia in response to local skin pinprick in rats. PubMed: Simultaneous determination of psychoactive compounds in foodstuffs using micellar liquid chromatography with direct injection. PubMed: Study on patients who underwent suspected diagnosis of allergy to amide-type local anesthetic agents by the leukocyte migration test. PubMed: Astringency is a trigeminal sensation that involves the activation of G protein-coupled signaling by phenolic compounds. PubMed: Lidocaine: cough (fentanyl induced). PubMed: An Approach to Heparin and Lidocaine Hypersensitivity for the Interventional Nephrologist. PubMed: Midface and perioral volume restoration: a conversation between the US and Italy. PubMed: Food for thought: atrioventricular dissociation. PubMed: Otologic iontophoresis: a no-papoose technique. PubMed: Biodegradable poly([D,L]-lactide-co-glycolide) nanofibers for the sustainable delivery of lidocaine into the epidural space after laminectomy. PubMed: Pain‑relieving effect of a compound isolated from white peony root oral liquid on acute radiation‑induced esophagitis. PubMed: Oligo-antigenic diet in the treatment of chronic anal fissures. Evidence for a relationship between food hypersensitivity and anal fissures. PubMed: Establishment of auditory discrimination and detection of tinnitus induced by salicylic acid and intense tone exposure in the rat. PubMed: Source memory in the rat. PubMed: Administration of anesthetic and analgesic prevent the suppression of many leukocyte responses following surgical castration and physical dehorning. PubMed: Anisomycin infusions in the parabrachial nucleus and taste neophobia. PubMed: Influence of the capillary diameter on the separation efficiency and sensitivity: a systematic approach. PubMed: Conditioned response to a magnetic anomaly in the Pekin duck (Anas platyrhynchos domestica) involves the trigeminal nerve. PubMed: Differential involvement of prelimbic and infralimbic medial prefrontal cortex in discrete cue-induced reinstatement of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) seeking in rats. PubMed: Rats answer an unexpected question after incidental encoding. PubMed: A comparison of the organization of longitudinal and circular contractions during pendular and segmental activity in the duodenum of the rat and guinea pig. PubMed: The prevalence and cost of unapproved uses of top-selling orphan drugs. PubMed: Topical anesthetics for dermatologic procedures: a review. PubMed: The role of the ventrolateral caudoputamen in predatory hunting. PubMed: Evaluation of the isoflurane-sparing effects of lidocaine infusion during umbilical surgery in calves. PubMed: Semiautomatic intraosseous devices in pediatric prehospital care. PubMed: Noradrenergic projections to the ventromedial hypothalamus regulate fat metabolism during endurance exercise. PubMed: Blood sampling in infants (reducing pain and morbidity). PubMed: The use of topical lidocaine to reduce pain during repetitive transcranial magnetic stimulation for the treatment of depression. PubMed: Update on treatments for premature ejaculation. PubMed: Minor beak trimming in chickens leads to loss of mechanoreception and magnetoreception. PubMed: Isoproterenol as an adjunct for treatment of idiopathic ventricular fibrillation storm in a pregnant woman. PubMed: Droperidol analgesia for opioid-tolerant patients. PubMed: Efficacy of articaine formulations: quantitative reviews. PubMed: Luminal serotonin time-dependently modulates vagal afferent driven antinociception in response to colorectal distention in rats. PubMed: Available and future therapies for premature ejaculation. PubMed: Effects of lidocaine on esophageal secondary peristalsis in humans. PubMed: Assessment: symptomatic treatment for muscle cramps (an evidence-based review): report of the therapeutics and technology assessment subcommittee of the American academy of neurology. PubMed: Regulation of bite force increase during splitting of food. PubMed: Cluster headache. PubMed: Ventricular tachyarrhythmias (out-of-hospital cardiac arrests). PubMed: Postherpetic neuralgia. PubMed: Off-label use of cardiovascular medications in children hospitalized with congenital and acquired heart disease. PubMed: [Intrauterine intestinal volvulus]. PubMed: 5-HT 3 receptors mediate the time-dependent vagal afferent modulation of nociception during chronic food allergen-sensitized visceral hyperalgesia in rats. PubMed: Blood sampling in infants (reducing pain and morbidity). PubMed: Isobaric (gasless) laparoscopic liver and kidney biopsy in standing steers. PubMed: An absorbable local anesthetic matrix provides several days of functional sciatic nerve blockade. PubMed: Spatiotemporal mapping of the motility of the isolated chicken caecum. PubMed: One-port video assisted laparoscopic kidney biopsy in standing steers. PubMed: A review of patent literature for iontophoretic delivery and devices. PubMed: [Pulmonary aspiration during anesthetic induction in a patient with a history of distal gastrectomy]. PubMed: Assessment of genotoxicity of Lidocaine, Prilonest and Septanest in the Drosophila wing-spot test. PubMed: Study on interaction between drug and membrane by using liposome coated zirconia-magnesia chromatography. PubMed: Update on pharmacotherapy guidelines for the treatment of neuropathic pain. PubMed: Topical anesthetic creams. PubMed: Hippocampal regulation of contextual cue-induced reinstatement of cocaine-seeking behavior. PubMed: Reporting a fatality during tumescent liposuction. PubMed: Cluster headache. PubMed: Five-year safety and efficacy of a novel polymethylmethacrylate aesthetic soft tissue filler for the correction of nasolabial folds. PubMed: Premature ejaculation: current and future treatments. PubMed: The use of compound topical anesthetics: a review. PubMed: Linker-based lecithin microemulsions for transdermal delivery of lidocaine. PubMed: [Case of intractable ventricula fibrillation by a multicomponent dietary supplement containing ephedra and caffeine overdose]. PubMed: Spatial cognition and memory: a reversible lesion with lidocaine into the anteromedial/posterior parietal cortex (AM/PPC) affects differently working and long-term memory on two foraging tasks. PubMed: Warnings for makers of compounded pain products. PubMed: Phase 1A safety assessment of intravenous amitriptyline. PubMed: Evaluation of lidocaine treatment and risk factors for death associated with gastric dilatation and volvulus in dogs: 112 cases (1997-2005). PubMed: Topical lidocaine for the treatment of postherpetic neuralgia. PubMed: The hippocampus plays a critical role at encoding discontiguous events for subsequent declarative memory expression in mice. PubMed: Effects of ventrolateral striatal inactivation on predatory hunting. PubMed: Postherpetic neuralgia. PubMed: Using intranasal lidocaine to reduce food intake. PubMed: Microemulsions as transdermal drug delivery vehicles. PubMed: The full stomach test as a novel diagnostic technique for identifying patients at risk of Brugada syndrome. PubMed: Lignocaine and chlorhexidine toxicity in children resulting from mouth paint ingestion: a bottling problem. PubMed: The "inverted cup" -- a novel in vitro release technique for drugs in lipid formulations. PubMed: Development of a technique for serial bilateral renal biopsy in steers. PubMed: Sedation and analgesia for gastrointestinal endoscopy during pregnancy. PubMed: A comparison of a needle-free injection system for local anesthesia versus EMLA for intravenous catheter insertion in the pediatric patient. PubMed: Ventricular tachyarrhythmias (out-of-hospital cardiac arrests). PubMed: Distribution of radioactive lidocaine injected into the testes in piglets. PubMed: Tolerability of treatments for postherpetic neuralgia. PubMed: Severe contact urticaria to guar gum included as gelling agent in a local anaesthetic. PubMed: Evaluation of middle and distal esophageal diverticuli with transnasal esophagoscopy. PubMed: Fatal case of BOTOX-related anaphylaxis? PubMed: From physical pharmacy to clinical pharmacology. PubMed: Analysis of lidocaine and its major metabolite, monoethylglycinexylidide, in elk velvet antler by liquid chromatography with UV detection and confirmation by electrospray ionization tandem mass spectrometry. PubMed: Pre-emptive effects of ibuprofen syrup and lidocaine infiltration on post-operative analgesia in children undergoing adenotonsillectomy. PubMed: Bi-hemispheric contribution to functional motor recovery of the affected forelimb following focal ischemic brain injury in rats. PubMed: The effect of bilateral lingual nerve anesthesia and increased occlusal vertical dimension on the onset of swallowing in adult males. PubMed: Intestinal electric stimulation decreases fat absorption in rats: therapeutic potential for obesity. PubMed: Perinatal hypothyroidism increases the susceptibility to lidocaine-kindling in adult rats. PubMed: Reversible inactivation of hippocampus and dorsolateral striatum in C57BL/6 and DBA/2 inbred mice failed to show interaction between memory systems in these genotypes. PubMed: Diagnostic techniques and clinicopathologic findings in ruminant neurologic disease. PubMed: Multimodal therapy for interstitial cystitis. PubMed: Hippocampal memory system function and the regulation of cocaine self-administration behavior in rats. PubMed: Lidocaine inactivation of ventral subiculum attenuates cocaine-seeking behavior in rats. PubMed: Modifiers of gastrointestinal motility of cattle. PubMed: Intra-hippocampal lidocaine injections impair acquisition of a place task and facilitate acquisition of a response task in rats. PubMed: Reversible inactivation of the hippocampal formation in food-storing black-capped chickadees (Poecile atricapillus). PubMed: [Postoperative ileus: part II (Clinical therapy)]. PubMed: Independent modulation of basal and feeding-evoked dopamine efflux in the nucleus accumbens and medial prefrontal cortex by the central and basolateral amygdalar nuclei in the rat. PubMed: Modulation by central and basolateral amygdalar nuclei of dopaminergic correlates of feeding to satiety in the rat nucleus accumbens and medial prefrontal cortex. PubMed: Local anesthetic toxicity--does product labeling reflect actual risk? PubMed: Comparison of HPLC and multivariate regression methods for hydrocortisone and lidocaine analysis of pharmaceutical preparations. PubMed: Collagen as a clinical target: nonoperative treatment of Dupuytren's disease. PubMed: Office-based transurethral microwave thermotherapy using the TherMatrx TMx-2000. PubMed: On the mechanism of colonic motility: the electric activation theory of colonic contraction. PubMed: Articaine, a new local anesthetic for American dentists: will it supersede lidocaine? PubMed: Two procedures establishing preference for oral cocaine and lidocaine solutions which do not use an associative history with a reinforcer. PubMed: An ethicist's commentary on animal welfare versus food safety in collecting antler velvet. PubMed: Alleviation of overtraining reversal effect by transient inactivation of the dorsal striatum. PubMed: Use of lignocaine (lidocaine) in food animals. PubMed: Use of lignocaine in food animals. PubMed: Serum leptin levels in patients with viral chronic hepatitis or liver cirrhosis. PubMed: Use of lignocaine in food animals. PubMed: New analgesics for neuropathic pain: the lidocaine patch. PubMed: Establishing oral preference for quinine, phencyclidine and caffeine solutions in rats. PubMed: Establishing preference for lidocaine solution to water: comparison between a fading and an abrupt-removal procedure for withdrawing a compound vehicle. PubMed: Products in dermatologic surgery: unapproved treatments or indications. PubMed: Role of sensation in swallowing function. PubMed: Cubic phases for studies of drug partition into lipid bilayers. PubMed: Hepatic chemoembolization: effect of intraarterial lidocaine on pain and postprocedure recovery. PubMed: Drug compatibility with the sponge phases formed in monoolein, water, and propylene glycol or poly(ethylene glycol). PubMed: Spectrum of gestational exposure to illicit drugs and other xenobiotic agents in newborn infants by meconium analysis. PubMed: The role of the pedunculopontine tegmental nucleus in relation to conditioned motor performance in the cat. II. Effects of reversible inactivation by intracerebral microinjections. PubMed: Cocaine discrimination: relationship to local anesthetics and monoamine uptake inhibitors in C57BL/6 mice. PubMed: D1 receptor modulation of hippocampal-prefrontal cortical circuits integrating spatial memory with executive functions in the rat. PubMed: Extralabel use of tranquilizers and general anesthetics. PubMed: The role of an amygdalo-nigrostriatal pathway in associative learning. PubMed: New drug approvals in 1996. PubMed: An evaluation of intraoral lidocaine patches in reducing needle-insertion pain. PubMed: Selective roles for hippocampal, prefrontal cortical, and ventral striatal circuits in radial-arm maze tasks with or without a delay. PubMed: Sucralfate for radiation mucositis: results of a double-blind randomized trial. PubMed: Schedule-induced polydipsic choice between cocaine and lidocaine solutions: critical importance of associative history. PubMed: The role of anterior ectosylvian cortex in cross-modality orientation and approach behavior. PubMed: Identification of 2,6-xylidine as a major lidocaine metabolite in human liver slices. PubMed: Local and regional anesthesia in ruminants and swine. PubMed: Comparative bioavailability and safety of two intramuscular ceftriaxone formulations. PubMed: Effects of cholestyramine and parenteral nutrition on hepatic metabolism of lidocaine: a study using isolated rat liver perfusion. PubMed: Unilateral amygdala inactivation after training attenuates memory for reduced reward. PubMed: Effects of taurine supplementation in parenteral nutrition-associated hepatosteatosis and lidocaine metabolism. A study using isolated rat liver perfusion. PubMed: Inactivation of hippocampus or caudate nucleus with lidocaine differentially affects expression of place and response learning. PubMed: Medial septal control of theta-correlated unit firing in the entorhinal cortex of awake rats. PubMed: The effect of liver disease and food on plasma MEGX concentrations. PubMed: Amygdala modulates memory for changes in reward magnitude: reversible post-training inactivation with lidocaine attenuates the response to a reduction in reward. PubMed: Oral cocaine as a reinforcer: acquisition conditions and importance of stimulus control. PubMed: Reversible lesions of the nucleus of the solitary tract attenuate the memory-modulating effects of posttraining epinephrine. PubMed: Individual variation in first-pass metabolism. PubMed: Influence of tactile stimulation of the rat gastric mucosa on blood flow and acid output. PubMed: Cocaine-like discriminative stimulus effects of procaine, dimethocaine and lidocaine in rats. PubMed: An extract of Gymnema sylvestre leaves and purified gymnemic acid inhibits glucose-stimulated gastric inhibitory peptide secretion in rats. PubMed: Very low calorie diets and pre-fasting prolonged QT interval. A hidden potential danger. PubMed: Gastric motility and food intake in rats after lesions of hypothalamic paraventricular nucleus. PubMed: Medication errors. PubMed: Stabilization by ethylenediaminetetraacetic acid of amide and other groups in drug compounds. PubMed: Antiarrhythmic properties of triamterene derivatives in the coronary artery ligated rat model. PubMed: New developments in pediatric dermatology. PubMed: Patient care threatened by presence of concentrated lidocaine syringes. PubMed: Antiarrhythmic properties of benzyl-triamterene derivatives in the coronary artery ligated and reperfused rat. PubMed: In vitro testing of triamterene derivatives for antiarrhythmic activity. PubMed: Factors affecting the voluntary intake of food by sheep. 5. The inhibitory effect of hypertonicity in the rumen. PubMed: Dangers of defibrillation: injuries to emergency personnel during patient resuscitation. PubMed: Effects of anaesthesia of human oral structures on masticatory performance and food particle size distribution. PubMed: Antiarrhythmic activity of the local anaesthetic fomocaine and some of its analogues. PubMed: Percutaneous endoscopic gastrostomy and jejunostomy for long-term feeding in patients with cancer of the head and neck. PubMed: Discriminative stimulus properties of local anesthetics in d-amphetamine- and pentobarbital-trained pigeons. PubMed: [Severe complications related to metabisulfites]. PubMed: Propafenone: a new antiarrhythmic agent. PubMed: New antiarrhythmic drugs: tocainide, mexiletine, flecainide, encainide, and amiodarone. PubMed: Severe dermatologic reactions reported after treatment with tocainide. PubMed: The influence of gastrointestinal infusions of glucose on regulation of food intake in pigs. PubMed: Lack of effects of prenatal exposure to lidocaine on development of behavior in rats. PubMed: Lethal/toxic injection of 20% lidocaine: a well-known complication of an unnecessary preparation? PubMed: Techniques of local analgesia in ruminants and swine. PubMed: Stability of sterile aqueous epinephrine injections submitted by U.S. hospitals. PubMed: Stability of sterile aqueous lidocaine hydrochloride and epinephrine injections submitted by U.S. hospitals. PubMed: Brain sites involved in the mediation of the behavioral effects of intraventricularly administered (-)-nicotine. PubMed: Use of cultured human conjunctival and other cells to assess the relative toxicity of six local anaesthetics. PubMed: Discriminative stimulus properties of cocaine in pigeons. PubMed: Injectable collagen: a six-year clinical investigation. PubMed: First-pass elimination. Basic concepts and clinical consequences. PubMed: Effects of local anesthetics on fixed-interval responding in rhesus monkeys. PubMed: Gnawing is the preferred consummatory behavior initially induced by tail pinch. PubMed: Effect of food on lidocaine kinetics: mechanism of food-related alteration in high intrinsic clearance drug elimination. PubMed: Food-animal regional anesthesia. Bovine blocks: continuous epidural anesthesia. PubMed: Suppression of mouse killing by lateral hypothalamic infusion of atropine sulfate in the rat: a general behavioral suppression. PubMed: [Evaluation of hepato-biliary functional scintigraphy with 99mTc diethyle-IDA. Findings in normal livers (author's transl)]. PubMed: Ventricular tachycardia in a patient with the "Chinese restaurant syndrome". PubMed: Acid and pepsin secretion of separated gastric pouches during perfusion of antral pouches with cholinergic stimulating and blocking agents and lignocaine. PubMed: Kinetics of the oral antiarrhythmic lidocaine congener, tocainide. PubMed: Evaluation of preparations of patent blue (Alphazurine 2G) dye for parenteral use. PubMed: Chemicals bathing the oxyntic gland area stimulate acid secretion in dog. PubMed: A further failure to replicate an effect of oral anesthesia on alcohol consumption by rats. PubMed: Differential effects of peripheral and central anosmia producing techniques on spontaneous behavior patterns. PubMed: Oral lignocaine: its absorption and effectiveness in ventricular arrhythmia control. PubMed: EFFECTS OF BACTERIAL ENDOTOXIN ON WATER INTAKE, FOOD INTAKE, AND BODY TEMPERATURE IN THE ALBINO RAT.