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Acute Toxicity of Tetramethylbenzenes: Durene, Isodurene and Prehnitene

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Acute Toxicity of Tetramethylbenzenes: Durene, Isodurene and Prehnitene DRUG AND CHEMICAL TOXICOLOGY, 1(3), 219-230 (1978) ACUTE TOXICITY OF TETRAMETHYLBENZENES : DURENE, ISODURENE AND PREHNITENE Dennis ;J. Lynch Vernon R. Perone Ronald L. Schuler William B. Ushry Trent rl. Lewis 3epartment of Bealth, Education, and Welfare Public Health Service Center for Disease Control National Institute for Occupational Safety and Health 4676 Columbia Parkway Cincinnati, Ohio 45226 ABSTRACT Oral LD50 (rat), primary skin irritation (rabbit), cutaneous sensitization (guinea pig) and eye irritation (rabbit) studies For personal use only. were conducted on the three tetramethylbenzene isomers: durene, isodurene and prehnitene. The order of oral toxicity was isodurene > prehnitene > durene. Durene was not a skin irritant, while isodurene and prehnitene each produced a mild positive skin response (erythema). None of the tetramethylbenzenes were skin sensitizers or eye irritants. qurene, isodurene and prehnitene are only slightly toxic on an acute toxicologic basis and only pose an acute health hazard when injested in excessive quantities. Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ. on 11/24/12 219 Copyright 0 1978 hy Marcel Dekker, InL All Rights Reserved Neither this work nor dny pdrt may be reproduced or transmitted in dny form or by any means, electronic or mechanicdl including photocopying, microfilming, and recording, or by any information storage and retrieval system without permission in writing from the publisher 220 LYNCH ET AL. INTRODUCTION Durene (1,2,4,5-tetramethylbenzene), isodurene (1,2,3,5- tetramethylbenzene) and prehnitene (1,2,3,4-tetramethylbenzene) are used as starting materials in the organic synthesis of plastics and resins. At room temperature durene is a solid, while the other isomers are liquids. Physical constants for the tetramethylbenzenes are presented in Table 1. TABLE 1 Physical Constants for Tetramethylbenzene Isomers 9 Durene Isodurene Prehnitene (1,2,4,5-tetra- (1,2,3,5-tetra- (1,2,3,4-tetra- methylbenzene) methylbenzene) methylbenzene) Formula '10H14 '10H14 '10H14 Mol Wt 134.22 134.22 134.22 Physical State Solid Liquid Liquid For personal use only. (21OC) Specific Gravity 0.838 0.890 0.905 Melting Point 79 -24 -6 ("C) Boiling Point 196.8 198 205 ("C) Flash Point 74 68 73 ("C) Solubility Insolub-3 Insolu Insolu Le Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ. on 11/24/12 (H20) Solubility - Organic Compounds Alcohol Very Soluble Very soluble Very soluble Ether Very soluble Very soluble Very soluble ACUTE TOXICITY OF TETRAMETHYLBENZENES 221 The tetramethylbenzenes are also important industrially because they possess extremely high reactivity relative to benzene and toluene, and they can form only one mono- and one di- nuclear derivative. This enables high yields of high purity products under relatively mild treatment conditions. 1 Durene is important for its oxidation product, pyromellitic anhydride, used in high molecular weight polymers, particularly in some engineering plastics. Durene has also been employed experi- mentally as a fungi~ide.~*~ In the course of production and utilization of tetramethyl- benzenes in industry, the working environment and employees may become contaminated. Data on the acute toxicity of the tetramethylbenzenes are sparse. Gerarde6 orally administered a homogenized suspension of durene (in olive oil warmed to 4OoC) to fasted 250g rats and had For personal use only. no deaths among the animals dosed. He determined that the oral LD was greater than 5000 mg/kg body weight. The oral LD for 50 50 durene has been estimated at 6800 mg/kg.? It is essential, therefore, to obtain additional data on the acute toxicity of industrial compounds in order to ascertain what health hazards, if any, are associated with their industrial uses. Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ. on 11/24/12 The present study describes the acute toxicity of durene, isodurene, and prehnitene for three routes of industrial exposure, i.e., oral, cutaneous and ocular. 222 LYNCH ET AL. METHODS The following compounds were studied: durene (1,2,4,5- tetramethylbenzene), isodurene (1,2,3,5-tetramethylbenzene) and prehnitene (1,2,3,4-tetramethylbenzene). The chemicals were analyzed for purity by gas chromatography using a flame ionization detector. The durene sample was better than 99+% pure; isodurene had a purity of 98% (the major impurity appeared to be prehnitene): and prehnitene was 96% pure (the major impurity appeared to be isodurene). All the test materials were administered undiluted, except for durene which was suspended in corn oil for the oral LD studies. 50 Acute Oral LD50. In rat oral LD50 studies, each test material was administered by gastric intubation as a single dose. The experimental subjects were male, cesarean-derived, Sprague-Dawley albino rats weighing 175-250g that were fasted overnight prior to For personal use only. dosing. Dose levels were seven to eight in number (durene 5200- 9800 mgfkg, prehnitene 4000-9000 mg/kg and isodurene 2000-8200 mg/kg). The number of rats employed per dose level was eight. The 14-day oral LD50 values and their 95% confidence limits were calculated by the exact probit analysis of Finney.8 When the data were nonlinear on log-probit graph paper, the moving average method of Thompson was employed .g Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ. on 11/24/12 Primary Skin Irritation. In the primary skin irritation studies, the three test materials and a negative control (distilled ACUTE TOXICITY OF TETRAMETHYLBENZENES 223 water), were tested on six rabbits, each rabbit receiving the three tetramethylbenzenes plus the distilled water control. For each test and control material, two skin sites were used, one abraded and one intact. A 0.1 ml volume or 100 mg (durene) of each undiluted test compound, and 0.1 ml of the control compound (distilled water) was applied to each 20 mm2 test site. The durene test sites were moistened with 1-2 ml of distilled water immediately prior to application of the test compound. The test sites were covered with a gauze patch. Each animal was provided with a leather harness to prevent the animal from disturbing the test site." Following a 24-hr exposure the harness and patches were removed and the skin reactions evaluated. A second evaluation was performed 48 hr after administration of the compounds. The method employed for determining the degree of primary skin irritation was a modification of the Draize For personal use only. technique." The reactions were evaluated on the basis of the designated values in the following table: React ion Intact Skin Abraded Skin No irritation 0 (Nonirritant) 0 (Nontoxic) Erythema (regard- 1 (Mild irritant) 1 (Xild cellular less of degree) toxicant) Erythema and edema 2 (Irritant) 2 (Cellular toxi- confined to test cant) area Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ. on 11/24/12 Erythema and edema 3 (Strong irritant) 3 (Strong cellular extending beyond toxicant) test area Eschar 4 (Corrosive) 4 (Corrosive) 224 LYNCH ET AL. Skin Sensitization. Fifteen male albiqo guinea pigs, weighing 300-400g, were employed for each test material in the repeated insult test for cutaneous sensitization. Five animals were assigned to the control group. The testing method was similar to that described by Landsteiner and Jacobs.13 A 0.1 ml volume or 100 mg (durene) of undiluted test compound was applied topically to separate abraded skin sites on the animals three times weekly for a total of nine treatments. Each durene test site was moistened with distilled water. Following a two week rest period for an immune response to develop, during which time no further treatments were made, a challenge dose of a test compound was administered to both test and control animals in the same dosage and by the same method used during the initial treatment period. Skin reactions were examined and recorded at 24, 48 and 72 hr following the challenge dose. For personal use only. Eye Irritation. Yale albino rabbits, weighing 2 to 3 kg, were used in the eye irritation studies. A 0.1 ml volume or 100 mg (durene) of each undiluted test material was placed in one eye of each animal by pulling the lower lid of the eye to form a cup into which the compound under investigation was instilled. The eyelids were held together for approximately one second and the animal was then released. The rabbit eye was exposed to the test Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ. on 11/24/12 compound for either 5 min or 24 hr before washing the eye with approximately 300 ml of distilled water over a 2 min period. The eyes were examined at 1, 24, 48 and 72 hr, and again at 7 days; ACUTE TOXICITY OF TETRAMETHYLBENZENES 225 if any injury persisted, the eyes were re-examined at 14 and 21 days. The nontreated eye served as a control. Grading of the severity of the eye irritation was performed according to the United States Food and Drug Administration method13 based upon the presence and degree of ulceration or opacity of the cornea and iris and erythema, chemosis and ulceration or necrosis of the conjuctival mucosa. RESULTS Acute Oral LD The oral LD values and their 95% confidence 50' 50 limits for the three test compounds are presented in Table 2. Isodurene was more toxic than prehnitene which was more toxic than durene. Lethal doses of the tetramethylbenzenes (durene > 6000 mgfkg, prehnitene and isodurene > 4400 mgfkg) induced stomach and intestinal hemorrhage, labored breathing, lacrimation, bladder distention and adhesions of abdominal organs For personal use only. (stomach, pancreas, spleen, liver and small intestines). Death was related to the degree of blockage of the gastrointestind tract from the resultant adhesions and/or leakage of bloody TABLE 2 Acute Oral LD50 Values in Rats Number of Animals Number Estimated LD50 95% Confidence Drug and Chemical Toxicology Downloaded from informahealthcare.com by Hacettepe Univ.
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