Adiphenine
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Adiphenine
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CAS No:
64-95-9
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Formula:
C20H25NO2
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Chemical Name:
Adiphenine
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Synonyms:
Benzeneacetic acid,α-phenyl-,2-(diethylamino)ethyl ester;Acetic acid,diphenyl-,2-(diethylamino)ethyl ester;Adiphenine;2-Diethylaminoethyl diphenylacetate;Difacil;Diphacil;Diphenylacetic acid diethylaminoethyl ester;Patrovine;Tranzetil;Trasentin;Trasentine;Adiphenin;SKF 962A;2-(Diethylamino)ethyl 2,2-diphenylacetate
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CAS No:
Characteristics
29.5
4.39 (est)
1.052g/cm3
112-114 °C
140-145 °C @ Press: 0.01 Torr
133.2ºC
1.544
In water, 1.89X10+1 mg/L at 25 deg C (est)
1.56X10-6 mm Hg at 25 deg C (est)
Henry's Law constant = 1.33X10-9 cu cm/molec-sec at 25 °C (est)
Hydroxyl radical reaction rate constant = 1.06X10-10 cu cm/molec-sec at 25 °C (est)
Safety Information
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.
Toxicity
ALTHOUGH THE DRUG IS RELATIVELY NONTOXIC, IT SHOULD NOT BE USED IN CLOSE SEQUENCE WITH MORPHINE; THE COMBINATION APPEARS TO CAUSE APPREHENSION & TACHYCARDIA. /ADIPHENINE HYDROCHLORIDE/|Spasmolytin (adiphenine hydrochloride) and tropicine were administered im to albino rats poisoned with anabasine sulfate doses of 346, 519, and 692 mg/kg administered through gastric tube. The LD50 of anabasine sulfate, determined for treatment with adiphenine hydrochloride, was 570 mg/kg, and 403 mg/kg for treatment with tropacine. The LD16 and LD84 values determined for treatment with adiphenine hydrochloride and tropacine were 460 and 712 mg/kg and 288 and 498 mg/kg, respectively. Adiphenine hydrochloride and tropacine, administered im in 20 mg/kg doses, reduced the LD50 of anabasine sulfate by 271% and 191%, respectively./Adiphenine hydrochloride/
LD50 rat intravenous 27 mg/kg|LD50 mouse oral 600 mg/kg|LD50 mouse subcutaneous 400 mg/kg|LD50 mouse intravenous 21.5 mg/kg|For more Non-Human Toxicity Values (Complete) data for ADIPHENINE (6 total), please visit the HSDB record page.
Drug Information
Parasympatholytics|MEDICATION (VET): AS A SMOOTH MUSCLE RELAXANT IN URINARY OR GASTROINTESTINAL SPASMS.|ADIPHENINE HAS BEEN EMPLOYED FOR SYMPTOMATIC RELIEF OF GI DISORDERS CHARACTERIZED BY SPASM; FOR SPASTIC CONDITIONS OF THE GALL BLADDER & BILIARY DUCTS; FOR DYSMENORRHEA; FOR URETERAL COLIC; & FOR NEUROGENIC BLADDER & CERTAIN OTHER TYPES OF DYSURIA. /ADIPHENINE HYDROCHLORIDE/|.../IT/ DECR SPASM OF GI TRACT, BILIARY TRACT, URETER, & UTERUS WITHOUT PRODUCING CHARACTERISTIC ATROPINE EFFECTS ON SALIVARY, SWEAT, GI GLANDS, EYE, OR CARDIOVASCULAR SYSTEM, EXCEPT IN LARGE DOSES. /ADIPHENINE HYDROCHLORIDE/|For more Therapeutic Uses (Complete) data for ADIPHENINE (10 total), please visit the HSDB record page.
ALTHOUGH THE DRUG IS RELATIVELY NONTOXIC, IT SHOULD NOT BE USED IN CLOSE SEQUENCE WITH MORPHINE; THE COMBINATION APPEARS TO CAUSE APPREHENSION & TACHYCARDIA. /ADIPHENINE HYDROCHLORIDE/
This study describes the behavior of a dual labelled drug, adiphenine, in the rat brain. Macroautoradiographies show images of the brain at different times after injection. Some of the tissue metabolites are identified at the brain level and the passage of the blood brain barrier is compared with tritiated water. The obtained data give very interesting indications on the blood brain distribution and on the metabolism at the brain level. Different techniques of high pressure liquid chromatography, macro- and histoautoradiographies allowed /visualization of/ how the drug is fixed on cerebral structures, giving indications on its mechanism of action.|The disposition of adiphenine labelled with 14C in two positions has been investigated in rats and mice after iv administration, and has been compared with that of the [14C]diethylethanolamine HCl and of the [14C]diphenylacetic acid. Radioactivity in the blood declined in a biphasic manner. Biliary elimination depended upon the 14C-labelled compound administered: less than 5% dose for the diethylethanolamine moiety, 100% dose for the carboxylic moiety. Of the radioactivity appearing in rat bile, less than 1% is associated with unchanged adiphenine. ... Uptake by the brain of [14C]adiphenine shortly after dosing is 15 times greater than that of blood. Radioactivity is also found in the hypophysis, the adrenals and melanoid pigments, with a concentration up to 30 times greater than that found in the blood.
Major metabolites isolated from rat urine after administration of a single dose of (14C)adiphenine or (3H)adiphenine were identified by chromatography and n.m.r. spectrometry, and by comparison with authentic reference compounds chemically synthesized. Adiphenine was extensively metabolized by hydrolysis of the ester bond into diethylaminoethanol, diphenylacetic acid, diphenylacetic acid glucuronide and, in small quantities, the corresponding glycine and glutamine conjugates.|The disposition of adiphenine labelled with 14C in two positions has been investigated in rats and mice after iv administration ... In preliminary metabolic studies, three major metabolites have been identified: diphenylacetic acid, diethylethanolamine and a diphenylacetic acid glucuronide.
Adiphenine was administered in 3H-labelled form in doses of 15 mumole/kg intravenously to male Wistar rats. Plasma and brain levels of the unchanged drug were measured. The elimination of the 3H-labelled compound from the plasma was monophasic with a half-life of 13 minutes. The unchanged drug was detectable in the plasma for 30 minutes after the injection. The time course of brain levels of unchanged drug paralleled that found in the plasma with a half-life of 9 to 12 minutes. In all experiments, brain and plasma levels of unchanged adiphenine correlate highly.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
adiphenine
Adiphenine Use and Manufacturing
PREPD BY ACTION OF DIPHENYLACETYL CHLORIDE OR DIPHENYL KETENE ON DIETHYLAMINOETHANOL: SWISS PATENT 190,541 (1937 TO CIBA); GER PATENTS 626,539; 653,778 (1937). /ADIPHENINE HYDROCHLORIDE/|Preparation: DE 626539 (1936 to Ciba)
Relaxant (smooth muscle).
Antiacid for relief of gastric hyperacidity /Carmethose-Trasentine/ /Former/
DETERMINATION OF ADIPHENINE BY METHOD UTILIZING SYNTHETIC ION EXCHANGE RESINS.|SIMPLE METHOD HAS BEEN DEVELOPED FOR DETERMINATION OF SPASMOLYTIC DRUGS. METHOD IS BASED ON INTERACTION OF SPASMOLYTIC COMPD WITH ACID DYE, BROMOCRESOL GREEN.|Analyte: adiphenine; matrix: solutions; procedure: high-performance liquid chromatography with ultraviolet detection at 260 nm; limit of quantitation: 7000 ng/mL
Analyte: adiphenine; matrix: tissue extracts; procedure: high-performance liquid chromatography with ultraviolet detection at 254 nm or radioactivity detection|HPLC determination in tissues.|Analyte: adiphenine; matrix: blood (serum), urine; procedure: capillary electrophoresis with ultraviolet detection at 190 nm; limit of detection: 174 ppb
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