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Procain
P · Novocaine · 2-(Diethylamino)ethyl 4-aminobenzoate · Novocain · Procain · Procine · Procaine powder · Procaine hydrochlori
Identifikatoren & physikalische Daten
| CAS No. | 59-46-1 |
|---|---|
| Summenformel | C13H20N2O2 |
| Durchschnittliche Molmasse | 236,31 g/mol |
| Monoisotopische Masse | 236,15247788 g/mol |
| SMILES | CCN(CC)CCOC(=O)c1ccc(N)cc1 |
| InChIKey | MFDFERRIHVXMIY-UHFFFAOYSA-N |
| PubChem CID | 4914 |
| ChEMBL | CHEMBL569 |
| ChEBI | CHEBI:8430 |
| EC No. | 200-426-9 |
| DTXSID | DTXSID7045021 |
| Lokaler Name | Procain |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 55,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 221 |
| Stoffklassen | Other Uses -> Pharmaceuticals |
| Arzneimittel | PharmaceuticalsPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | log Kow= 1.921.82.1 |
| Color/Form | Anhydrous plates, tables from ligroin or ether |
| Löslichkeit | Crystals, mp 153-156 °C, sol in water, alcohol /Nitrate/Crystals. Six-sided plates, monoclinic or triclinic, mp 153-156 °C. One gram dissolves in 1 ml water and in 30 ml alcohol. Slightly sol in chloroform. Almost insoluble in ether. The pH of a 0.1 M aqueous solution is 6.0. /Hydrochloride/ODORLESSAQ SOLN ACID TO LITMUSPKA 8.7SMALL WHITE CRYSTALS1 G SOL IN 1 ML WATER OR 15 ML ALCSLIGHTLY SOL IN CHLOROFORMPRACTICALLY INSOL IN ETHER /HYDROCHLORIDE/Sol in alcohol, ether, benzene, chloroformSoluble in ethanol, ethyl ether, and benzeneDMSO (Slightly), Methanol (Slightly)9.45g/L(30 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnesthetics, Local |
| Animal Drugs | Pharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Decomposition | When heated to decomposition it emits toxic fumes of nitroxides. |
| Schmelzpunkt | 61 °CSlightly bitter tastemp: 51 °Cneedles from aq alcohol /Dihydrate/61° |
| Brechungsindex | INDEX OF REFRACTION: 1.5611 @ 25 °C/D /HYDROCHLORIDE/1.5430 (estimate) |
| Physical Description | Solid |
| Siedepunkt | 378.78°C (rough estimate) |
| Dichte | 1.0604 (rough estimate) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 9.04±0.01(H2O,t=25,I=0.1(NaCl))(Approximate) |
| Farbe | White to Off-White |
| Merck | 14,7757 |
| Stabilität | Hygroscopic |
| InChI | InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3 |
| InChIKey | MFDFERRIHVXMIY-UHFFFAOYSA-N |
| SMILES | C(OCCN(CC)CC)(=O)C1=CC=C(N)C=C1 |
| CAS Datenbank | 59-46-1(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, 4-amino-, 2-(diethylamino)ethyl ester(59-46-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Procaine: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Allergic contact dermatitis reported in doctors, dentists, and veterinarians[Kanerva, p. 1829] Procaine allergy used to be a common skin sensitizer for dentists. There exists cross-reactivity between procaine, benzocaine, and tetracaine but not with lidocaine and other amide-type local anesthetics currently used. [Kanerva, p. 434] |
| FDA-Anforderungen | 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 amended21 U.S.C. 321-392). |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Entsorgungsverfahren | 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. |
| Wechselwirkungen | WELL-KNOWN CLASS OF PROLONGING AGENTS...SKF-525-A...INHIBITS...MICROSOMAL ESTERASE ACTIVITY TOWARDS PROCAINE.... /PROCAINE/ IS HYDROLYZED IN VIVO TO PRODUCE PARAAMINOBENZOIC ACID, WHICH INHIBITS THE ACTION OF SULFONAMIDES. THUS, LARGE DOSES SHOULD NOT BE ADMINISTERED TO PATIENTS TAKING SULFONAMIDE DRUGS.PROCAINE IM CAN POTENTIATE PENTOBARBITAL ANESTHESIA... SYMPATHOMIMETICS...& MONOAMINE OXIDASE INHIBITORS MAY HAVE THEIR HYPERTENSIVE EFFECTS POTENTIATED BY PROCAINE. ...MAY POTENTIATE OR BE POTENTIATED BY PHENOTHIAZINE TRANQUILIZERS, CHOLINESTERASE INHIBITORS...& MUSCLE RELAXANTS SUCH AS SUCCINYLCHOLINE.SUBSTRATE COMPETITION PROBABLY ACCOUNTS FOR INHIBITION OF SUCCINYLCHOLINE HYDROLYSIS BY PROCAINE.For more Interactions (Complete) data for PROCAINE (17 total), please visit the HSDB record page. |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin.The adverse effects of procaine administration are similar to those of other aminoester anesthetics. Increased intravascular levels mediate most side effectsthis can be due to overdosage, entry into intravascular spaces, and potentiation from reduced metabolism. More rarely, patients may experience adverse effects secondary to hypersensitivity or idiosyncrasy. |
| Expositionspfade | Oral, Infiltration, Intramuscular |
| Toxizitätsübersicht | Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Procaine has also been shown to bind or antagonize the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex. |
| Signs and Symptoms | An allergic reaction (difficulty breathingclosing of the throatswelling of the lips, tongue, or faceor hives)chest pain or slow or irregular heartbeatsdizziness or drowsinessanxiety or restlessnessnausea or vomitingtrembling, shaking, or seizures (convulsions). Other less serious side effects such as numbness, tingling, or minor pain at or around the injection site are more likely to occur.(L1459) |
| Human Toxicity Excerpts | IN 2...INSTANCES LOSS OF VISION FOLLOWED INJECTION OF PROCAINE FOR EXTRACTION OF TEETH. IN ONE OF THESE INSTANCES SEVERE VISUAL LOSS WAS NOTED WITHIN DAY FOLLOWING EXTRACTION & THERE WAS NO SUBSEQUENT IMPROVEMENT. ULTIMATELY OPTIC NERVES BECAME ATROPHIC & VISION WAS /SRP: REDUCED TO/ PERCEPTION OF HAND MOVEMENT. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Non-Human Toxicity Excerpts | RAPID IV ADMIN OR OVERDOSAGE CAN CAUSE CONVULSIONS, HYPOTENSION, RESPIRATORY FAILURE, & EVEN DEATH. ... HYPERSENSITIVITY REACTIONS ARE POSSIBLE.FOLLOWING ABSORPTION FROM PARENTERAL ROUTES, PROCAINE IS A CENTRAL NERVOUS STIMULANT, PRODUCING RESTLESSNESS & TREMORS PROCEEDING TO CLONIC CONVULSIONS. STIMULATION IS FOLLOWED BY DEPRESSION, & DEATH IS USUALLY DUE TO RESPIRATORY FAILURE. ... ON RARE OCCASIONS SMALL DOSES HAVE PRODUCED CARDIOVASCULAR COLLAPSE & DEATH. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Toxicity Data | LD50: 350 mg/kg (Oral, mouse). |
| Non-Human Toxicity Values | LD50 Rat sc 600 mg/kgLD50 Mouse oral 350 mg/kgLD50 Mouse ip 124 mg/kgLD50 Mouse sc 300 mg/kgLD50 Mouse iv 45 mg/kg |
| UN-Transportnummer | 3249 |
| Zollcode | 2922.49.3700 |
| RTECS-Nr. | DG2100000 |
| Toxizität | LD50 in mice (mg/kg): 195 i.p.45 i.v. (North, Urbach) |
| Gefahrenklasse | 6.1(b) |
| Verpackungsgruppe | III |
| Gefahrstoffdaten | 59-46-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Procaine is a local anesthetic with a para-amino function. Sensitization mainly concerns medical, dental and veterinary professions.
Verwenden
Procaine (Novocain) is mainly used in dental or medical procedures requiring infiltration anesthesia, peripheral block, or spinal block.