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2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide(CAS No. 137-58-6)

2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide C14H22N2O (cas 137-58-6) Molecular Structure

137-58-6 Structure

Identification and Related Records

【Name】
2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide
【Iupac name】
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
【CAS Registry number】
137-58-6
【Synonyms】
Lidocaine Base
Lignocaine
2-diethylaminoacet-2,6-xylidide
Lidocaine
【EINECS(EC#)】
205-302-8
【Molecular Formula】
C14H22N2O (Products with the same molecular formula)
【Molecular Weight】
234.34
【Inchi】
InChI=1/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
【InChIKey】
NNJVILVZKWQKPM-UHFFFAOYSA-N
【Canonical SMILES】
CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
【MOL File】
137-58-6.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.026g/cm3
【Melting Point】
66-69℃
【Boiling Point】
350.8°Cat760mmHg
【Vapour】
4.28E-05mmHg at 25°C
【Flash Point】
166°C
【Water】
practically insoluble
【Solubilities】
Slightly soluble
【Color/Form】
Needles from benzene or alc
WHITE OR SLIGHTLY YELLOW, CRYSTALLINE POWDER
White or slightly yellow, crystalline powder
【Stability】
Stable. Incompatible with strong oxidizing agents.
【Storage temp】
Store in a cool, dry place. Keep container closed when not in use.
【Spectral properties】
MASS: 1594 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Intense mass spectral peaks: 58 m/z, 72 m/z, 86 m/z, 234 m/z
【Computed Properties】
Molecular Weight:234.33728 [g/mol]
Molecular Formula:C14H22N2O
XLogP3:2.3
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:5
Tautomer Count:3
Exact Mass:234.173213
MonoIsotopic Mass:234.173213
Topological Polar Surface Area:32.3
Heavy Atom Count:17
Formal Charge:0
Complexity:228
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:1
Effective Rotor Count:6
Conformer Sampling RMSD:0.8
CID Conformer Count:7

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22
【Safety Statements 】
S22;S26;S36
【HazardClass】
6.1(b)
【Safety】

Safety Information of?Lidocaine (CAS NO.137-58-6):
Hazard Codes:HarmfulXn
Risk Statements:22
R22:Harmful if swallowed?
Safety Statements:22-26-36
S22:Do not breathe dust
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing?????
RIDADR:3249
WGK Germany:3
RTECS:AN7525000
HazardClass:6.1(b)
PackingGroup:III
Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: blood pressure lowering, changes in heart rate, coma, convulsions, distorted perceptions, dyspnea, excitement, hallucinations, muscle contraction or spasticity, pulse rate, respiratory depression, toxic psychosis. An experimental teratogen. Other experimental reproductive effects. A local anesthetic. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

【PackingGroup 】
III
【Transport】
25kgs
【Formulations/Preparations】
SOME INJECTIONS OF LIDOCAINE HYDROCHLORIDE CONTAIN EPINEPHRINE TO DELAY ABSORPTION, PROLONG ITS ACTION, & REDUCE ITS TOXIC EFFECTS. /LIDOCAINE HYDROCHLORIDE/
(LIGNOCAINE; XYLOCAINE, OTHERS) ... PREPN INCL INJECTIONS, & OINTMENTS, JELLY, TOPICAL SOLN & TOPICAL AEROSOL. FOR ORAL MUCOSA MARKET PREPN (0.5 TO 4.0%), SOME WITH & WITHOUT EPINEPHRINE (1:150,000 TO 1:200,000), ARE SUITABLE FOR INFILTRATION (0.5%), BLOCK (1 TO 2%), & TOPICAL MUCOSAL ANESTHESIA (1 TO 2%). /LIDOCAINE HYDROCHLORIDE/
INJECTIONS, USP (XYLOCAINE), IS AVAILABLE FOR IV ADMIN ... SOLUTION FOR IM INJECTION ... INJECTION CONTAINS NO PRESERVATIVE, SYMPATHOMIMETICS, OR OTHER VASOCONSTRICTOR. /LIDOCAINE HYDROCHLORIDE/
Grade: USP
【Exposure Standards and Regulations】
Lidocaine injection with epinephrine. (a) Animal drug specifications: Each ml of the drug contains 20 mg (2%) of lidocaine hydrochloride, 0.01 mg of epinephrine, with sodium chloride, and with methylparaben as a preservative, in water for injection ... (c) Conditions of use: (1) Amt: The drug is administered by injection as a 2% soln or diluted with bacteriostatic water for injection to a 0.5% soln for local anesthesia of ... (i) Cats: Administer approximately 2 ml of 2% soln with epinephrine by caudal injection. (ii) Cattle: Administer 5 ml of 2% soln with epinephrine by epidural injection (standing animal). Administer 10 to 20 ml of 2% soln with epinephrine by cornural nerve block injection. For teat operations and infiltration, inject 0.5% soln with epinephrine to effect. (iii) Dogs: Administer 2 to 10 ml of 2% soln with epinephrine by caudal injection. Do not give intravascularly. For infiltration, administer 0.5% soln with epinephrine to effect. (iv) Horses: Administer 5 to 10 ml of 2% soln with epinephrine by volar nerve block. Administer 10 to 15 ml of 2% soln with epinephrine by epidural injection. For standing animal, apply slowly and observe individual sensitivity. For infiltration, administer 0.5% soln with epinephrine to effect. Limitations: (i) The drug is contraindicated in the presence of sepsis in the region of proposed injection, shock and heart block, neurologic disease, spinal deformities, septicema, and hypertension. (ii) Do not give intravascularly. (iii) Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Lidocaine with epinephrine/
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

First Aid Measures of Lidocaine (CAS NO.137-58-6):
Ingestion:If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Storage of Lidocaine (CAS NO.137-58-6):
Store in a cool, dry place. Keep container closed when not in use.
Synonyms of?Lidocaine (CAS NO.137-58-6) are?2',6'-Acetoxylidide, 2-(diethylamino)- ;?2-(Diethylamino)-2',6'-acetoxylidide ;?2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide ;?4-12-00-02538 (Beilstein Handbook Reference) ;?Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- ;??Alphacaine ;?Anbesol ;?Anestacon ;?BRN 2215784 ;?Cappicaine ;?Cito optadren ;?Cuivasil ;?DentiPatch ;?Diethylaminoaceto-2,6-xylidide ;?Duncaine ; ;?ELA-Max ;?Esracaine ;?Gravocain ;?HSDB 3350 ;?Isicaina ;?Isicaine ;?Jetocaine ;?L-Caine ;?Leostesin ;?Lida-Mantle ;?Lidocaina ;?Lidocainum ;Maricaine ;?Remicaine ;?Rucaina ;?Solarcaine ;?Solcain ;??Xilina ;?Xilocaina ;?Xycaine ;?Xylestesin ;?Xylocain ;?Xylocaine ;?Xylocitin ;?Xyloneural (free base) ;?Xylotox ;?alfa-Dietilamino-2,6-dimetilacetanilide ;?alfa-Dietilamino-2,6-dimetilacetanilide [Italian] ;?alpha-Diethylamino-2,6-dimethylacetanilide

【Octanol/Water Partition Coefficient】
log Kow= 2.26 @ pH 7.4
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

LIDOCAINE HYDROCHLORIDE INJECTION IS USUALLY PREPD IN SOLN BY ACTION OF DIL HYDROCHLORIDE ON LIDOCAINE BASE. /LIDOCAINE HYDROCHLORIDE/
BY CHLOROACETYLATION OF 2,6-XYLIDINE & CONDENSATION OF RESULTING CHLOROACETOXYLIDIDE & 6-ETHYLAMINE.
It is synthesized from 2,6-xylidine by chloroacetylation to give the chloroacetanilide which reacts with diethylamine to give lidocaine.
By action of diethylamine on chloroacetylxylidide.
【Usage】

Medication.

Biomedical Effects and Toxicity

【Biological Activity】
Anasthetic and class Ib antiarrhythmic agent.? Blocks voltage-gated sodium channels in the inactivated state.
【Pharmacological Action】
- Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
- Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
【Therapeutic Uses】
Anesthetics, Local; Anti-Arrhythmia Agents
Lidocaine is a local anesthetic which also is useful in the acute intravenous therapy of ventricular arrhythmias. When lidocaine was administered to all patients with suspected myocardial infarction, the incidence of ventricular fibrillation as reduced. However, survival to hospital discharge tended to be decrease ...
LIDOCAINE PRODUCES FASTER, MORE INTENSE, LONGER-LASTING, & MORE EXTENSIVE ANESTHESIA THAN DOES AN EQUAL CONCN OF PROCAINE. UNLIKE PROCAINE, IT IS AN AMINOETHYLAMIDE ... IT IS A GOOD CHOICE FOR INDIVIDUALS SENSITIVE TO ESTER-TYPE LOCAL ANESTHETICS.
LIDOCAINE IS EFFECTIVE AGENT FOR TREATMENT OF LIFE-THREATENING VENTRICULAR TACHYARRHYTHMIAS ... IT IS NOT VERY EFFECTIVE AGAINST ARRHYTHMIAS OF ATRIAL ORIGIN. WIDESPREAD USE ... LARGELY EXPLAINED BY ... ABILITY TO SUPPRESS VENTRICULAR TACHYARRHYTHMIAS WITH MUCH LESS IMPAIRMENT OF CARDIAC FUNCTION THAN ... QUINIDINE & PROCAINAMIDE.
LOCAL ANESTHETICS IN DENTISTRY: IONTOPHORESIS OF EPINEPHRINE-LIDOCAINE MIXTURE APPEARS TO BE USEFUL. [GANGAROSA LP SR; J DENT RES 60 (8): 1471 (1981)]
【Biomedical Effects and Toxicity】
... ELIMINATION HALF-LIFE IN NORMAL PERSONS IS APPROX 90 MIN ... .
DRUGS RECENTLY SHOWN TO ACTIVELY CROSS HUMAN PLACENTA INCL ... LIDOCAINE ... .
BLOOD & TISSUE LEVELS ... EXAMINED IN DOGS AFTER BOLUS INJECTION, IV INFUSION, & BOLUS INJECTION FOLLOWED BY IV INFUSION. ... TISSUE LEVELS OF UNCHANGED DRUG VARIED ... HIGHEST CONCN ... IN KIDNEY, & LOWEST IN HEART. MAX TISSUE LEVELS OF (3)H-LIDOCAINE & METABOLITES ... OBTAINED 30 MIN AFTER IV OR ORALLY DOSING TO RATS ... .
/AFTER IV OR ORAL DOSING OF (3)H-LIDOCAINE TO RATS/ PEAK INTESTINAL RADIOACTIVITY ... REACHED 2-4 HR AFTER EACH TREATMENT. LITTLE (3)H IS VOIDED IN FECES, SUGGESTING EXTENSIVE ENTERO-HEPATIC CIRCULATION OF LIDOCAINE & ITS METABOLITES. HIGHER PLASMA LEVELS ... WERE OBTAINED IN PATIENTS FROM IM INJECTION OF DIL SOLN THAN MORE CONCN ... .
ESSENTIALLY NO LIDOCAINE IS EXCRETED UNCHANGED IN URINE. ... CLEARANCE OF LIDOCAINE APPROACHES RATE OF HEPATIC BLOOD FLOW & IS THUS VERY SENSITIVE TO CHANGES IN THIS PARAMETER. CLEARANCE OF LIDOCAINE ALSO MAY DECR AS RESULT OF PROLONGED INFUSION. HALF-TIME FOR ELIMINATION OF LIDOCAINE IS NORMALLY ABOUT 100 MIN.
/LIDOCAINE/ ... IS ALMOST COMPLETELY ABSORBED AFTER IM ADMIN. ABOUT 50% OF LIDOCAINE IN PLASMA IS BOUND TO ALBUMIN @ THERAPEUTIC CONCN ... DISTRIBUTION IS RAPID, & APPARENT VOL OF DISTRIBUTION ... IS NORMALLY ABOUT 1 L/KG; THIS VOL IS SUBSTANTIALLY REDUCED IN PATIENTS WITH HEART FAILURE.
Lidocaine is well absorbed, but undergoes extensive, though variable, first-pass hepatic metabolism ... Lidocaine is absorbed rapidly after perenteral admin & from the gastrointestinal and respiratory tracts.
THE UNCHANGED FORM OF LIDOCAINE IS EXCRETED IN URINE OF THE DOG IN A CONCENTRATION OF 10-20%.
THE LIVER OF THE FETAL GUINEA PIG IS THE ONLY ORGAN IN WHICH LIDOCAINE IS FOUND IN HIGHER CONCN THAN IN THE MATERNAL SUBJECT.
Lidocaine readily crosses the blood-brain barrier and the placenta. Lidocaine also is distributed into milk; in one lactating women, milk lidocaine concentration was approximately 40% of the serum concentration (from a sample obtained 2 hours earlier).
After intravenous injection, lidocaine rapidly enters the heart and the brain, producing effects within minutes. Subsequently, concentrations in the blood and highly perfused tissues (such as the brain and the heart) fall, because of distribution to slowly perfused tissues, primarily skeletal muscle and fat. The initial distributional decline in blood concentrations follows a half-life of about 10 minutes and explains why in some cases the antiarrhythmic action of lidocaine disappears in 10 or 20 minutes after the initial bolus dose. The peak concentration achieved in the blood prior to tissue distribution of the lidocaine depends on the rate of administration. For this reason, a patient can experience a seizure or other transient central nervous system toxicity shortly after a rapid bolus injection, but concentrations of lidocaine may be subtherapeutic when measured a few minutes later. Distribution kinetics are not so important in understanding the course of effects or toxicity of lidocaine when it is used for local anesthesia or after oral ingestion of it or other type IB antiarrhythmic drugs.
The plasma concn of lidocaine and prilocaine after dermal application of EMLA cream 5% were determined in two clinical studies. The cream (10-16 g) was applied to a total surface area of 100-160 cm2. Each area was covered by a Tegaderm dressing (3M) in order to obtain occlusion. An application time of 2 hr was used. Two age groups of ten children were studied: 2-3 yr and 6-8 yr. In both groups venous blood samples were drawn prior to application and at 2, 3, 4 and 5 hr. In addition, in one of the studies, the cream was used during the surgical removal of mollusca in order to study the analgesic effect of the cream. The absorption of the local anaesthetics as indicated by plasma concn was far below toxic levels. The highest individual concn of lidocaine was 315 ng/ml and of prilocaine 215 ng/ml. The analgesic effect was sufficient--eight out of ten patients experienced no or slight pain. Transient local reactions (paleness, redness) were frequently observed. In one patient with eczema present at the application site prior to the application, a reaction persisted for one week. Dermal analgesia provided by EMLA is a safe and effective method for alleviation of pain from removal of mollusca and the plasma concn are innocuous. [Haugstvedt S et al; Z Kinderchir 45 (3): 148-50 (1990)] PubMed Abstract
To test the hypothesis that lidocaine passage into the CNS is a function of free rather than total lidocaine concn, the effect of serum protein binding on the distribution of lidocaine into brain and CSF was examined in dogs. Six of the 13 dogs studied were pretreated with rifampin to induce a 4 fold increase (p = 0.019) in serum concn of alpha 1-acid glycoprotein, which is a major binding protein for lidocaine. The dogs wer anesthetized and prepared surgically to obtain samples of cortical brain tissue or CSF from the cisterna magna. Lidocaine at a dose of 3 mg/kg was infused iv over 15 sec. Arterial blood and brain cortex or CSF were sampled serially during a 60 min interval and analyzed for lidocaine content. Unbound or free fraction of lidocaine in serum was measured by equilibrium dialysis. Rifampin pretreatment led to a significant decrease in average serum free fraction of lidocaine, from 0.24 + or - 0.08 to 0.080 + or - 0.030 (p PubMed Abstract
Ten intensive care patients and five healthy volunteers each received a bolus injection of lidocaine hydrochloride (100 mg, 2%) over an injection period of 5 sec. After 0.5, 1, 2, 4, 8, 15 and 25 min arterial, central venous and peripheral venous blood samples were collected. In four of the volunteers, arterial and central venous samples were also taken about 10 sec after the end of injection. The fluorescence polarization method by means of the Abbott-TDx system was used, and plasma concn of lidocaine were determined. The measurements showed that lidocaine levels in central venous plasma 10 sec after the end of administration were higher than those in arterial plasma. By 30 sec after administration the opposite situation had developed, so that arterial concn were higher than those in central venous plasma. This relation did not change throughout the study, though the two levels became closer, as is shown by the ratios .... Concn in peripheral venous plasma increased more slowly but remained far below those in arterial and central venous plasma, at least for the first 8 min. After 15 min lidocaine levels were almost the same in all three samples. During the entire study there were no ECG changes, and neither heart rate nor blood pressure showed any significant deviation from the values obtained at the beginning. The volunteers had minor toxic manifestations, such as dizziness, tinnitus and a metallic taste in the mouth; one person had a sensation of pressure in his chest, which improved following oxygen administration. /Lidocaine hydrochloride/ [Nolte H et al; Reg Anaesth 13 (2): 29-35 (1990)] PubMed Abstract
The pharmacokinetics of an epidural injection of bupivacaine, lidocaine and mepivacaine were studied in 30 patients (aged 18-70 yr) undergoing surgery. Time to reach maximum concn was 10.5 min for bupivacaine, 20 min for mepivacaine and 25 min for lidocaine. Absorption rate constants were 0.42, 0.21 and 0.17/min for bupivacaine, mepivacaine and lidocaine, respectively. Elimination of bupivacaine was significantly slower than that of the other drugs. Mean half-lives of bupivacaine, lidocaine and mepivacaine were 150 min, 94 min and 100 min, respectively. It was concluded that absorption of epidural bupivacaine, lidocaine and mepivacaine is rapid, with bupivacaine showing the fastest absorption and slowest elimination.
A study to evaluate the effect of age on lidocaine absorption and metabolism after application to the oropharynx and vocal cords was conducted in 2 groups of 5 healthy volunteers, aged 25 to 37 yr and 60 to 68 yr, who received a total of 300 mg of lidocaine hydrochloride (Xylocaine) administered as a gargle, gel, or directly to the vocal cords. No differences in peak plasma lidocaine concn in young subjects, and in young-elderly subjects, or lidocaine AUC were seen between the 2 age groups. This study suggests that over the age range studied, increased age does not impair lidocaine absorption from the oropharynx or lidocaine metabolism when topical lidocaine is used during flexible fiberoptic bronchoscopy.
After local perineal infiltration for episiotomy, lidocaine was found in neonatal urine for at least 48 hr after delivery.

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