(±)-Brompheniramine
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(±)-Brompheniramine
structure -
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CAS No:
86-22-6
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Formula:
C16H19BrN2
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Chemical Name:
(±)-Brompheniramine
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Synonyms:
2-Pyridinepropanamine,γ-(4-bromophenyl)-N,N-dimethyl-;Pyridine,2-[p-bromo-α-[2-(dimethylamino)ethyl]benzyl]-;γ-(4-Bromophenyl)-N,N-dimethyl-2-pyridinepropanamine;2-[p-Bromo-α-(2-dimethylaminoethyl)benzyl]pyridine;1-(p-Bromophenyl)-1-(2-pyridyl)-3-dimethylaminopropane;3-(p-Bromophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamine;Brompheniramine;Parabromdylamine;Bromopheniramine;Parabromodylamine;(±)-Brompheniramine;Bromphen;[3-(4-Bromo-phenyl)-3-pyridin-2-yl-propyl]-dimethyl-amine;32188-07-1;156428-33-0
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CAS No:
Description
ChEBI: Pheniramine in which the hydrogen at position 4 of the phenyl substituent is substituted by bromine. A histamine H1 receptor antagonist, brompheniramine is used (commonly as its maleate salt) for the symptomatic relief of allergic cond tions, including rhinitis and conjunctivitis.
Solid
Brompheniramine is pheniramine in which the hydrogen at position 4 of the phenyl substituent is substituted by bromine. A histamine H1 receptor antagonist, brompheniramine is used (commonly as its maleate salt) for the symptomatic relief of allergic conditions, including rhinitis and conjunctivitis. It has a role as a H1-receptor antagonist and an anti-allergic agent. It is a member of pyridines and an organobromine compound.|Histamine H1 antagonist used in treatment of allergies, rhinitis, and urticaria.|Brompheniramine and chlorpheniramine maleate are first generation antihistamines that are widely used to treat symptoms of allergic rhinitis and the common cold. Clinically apparent liver injury from brompheniramine or chlorpheniramine must be exceeding rare, if it occurs at all.
(±)-Brompheniramine Basic Attributes
319.24
319.24
201-657-8
DTXSID5022691
Oily liquid with slightly yellow color
R - Respiratory system
Characteristics
16.1
4.06 (est)
Solid
1.265 g/cm3
<25 °C
147-152 °C @ Press: 0.5 Torr
197.5ºC
1.577
Freely soluble (maleate salt)
Preparations containing brompheniramine maleate generally should be stored in tight, light-resistant containers at a controlled room temperature between 15 - 30 deg C.
4.63X10-5 mm Hg at 25 deg C (est)
Characteristic amine-like
Henry's Law constant = 2.19X10-10 atm-cu m/mol at 25 °C (est)
Hydroxyl radical reaction rate constant = 8.54X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
SENSITIVE TO LIGHT /BROMPHENIIRAMINE MALEATE/
P264, P270, P301+P312, P330, P501
H302
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.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription and over-the-counter drug products, incl brompheniramine maleate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Brompheniramine maleate/|Cold, cough, allergy, bronchodilator, and antiasthmatic drug products for over-the-counter human use. ... Antihistamine active ingredients: The active ingredient of the product consists of brompheniramine maleate when used within the dosage limits established for the ingredient. /Brompheniramine maleate/
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory.
Toxicity
Oral, rat: LD50 = 318 mg/kg. Signs of overdose include fast or irregular heartbeat, mental or mood changes, tightness in the chest, and unusual tiredness or weakness.
Despite widespread use, the first generation antihistamines such as brompheniramine and chlorpheniramine have rarely been linked to liver test abnormalities or to clinically apparent liver injury. A single case report of clinically apparent liver injury with jaundice attributed to dexchlorpheniramine was reported from France. The time to onset was 10 days, and the clinical presentation resembled acute viral hepatitis, with marked elevations in serum aminotransferase levels and jaundice. Recovery was rapid and complete, but jaundice and hepatitis recurred within 10 days of restarting. Immunoallergic features (rash, fever, eosinophilia) were absent as were autoantibodies. Interestingly, the patient tolerated other antihistamines (cetirizine) without difficulty.
Concurrent use /of ototoxic medications/ with antihistamines may mask the symptoms of ototoxicity such as tinnitus, dizziness, or vertigo. /Antihistamines/|Concurrent use of monoamine oxidase (MAO) inhibitors with antihistamines may prolong and intensify the anticholinergic and CNS depressant effects of antihistamines; concurrent use is not recommended. /Antihistamines/|Concurrent use /with alcohol or other CNS depression-producing medications/ may potentiate the CNS depressant effects of either these medications or antihistamines; also, concurrent use of maprotiline or tricyclic antidepressants may potentiate the anticholinergic effects of either antihistamines or these medications. /Antihistamines/|Anticholinergic effects may be potentiated when /anticholinergics or other medications with anticholinergic activity/ are used concurrently with antihistamines; patients should be advised to report occurrence of gastrointestinal problems promptly since paralytic ileus may occur with concurrent therapy. /Antihistamines/|For more Interactions (Complete) data for BROMPHENIRAMINE (6 total), please visit the HSDB record page.
Use is not recommended in newborn or premature infants because this age group has an increased susceptibility to anticholinergic side effects, such as central nervous system excitation, and an increased tendency toward convulsions. A paradoxical reaction characterized by hyperexcitability may occur in children taking antihistamines. /Antihistamines/|Dizziness, sedation, confusion, and hypotension may be more likely to occur in geriatric patients taking antihistamines. Geriatric patients are especially susceptible to the anticholinergic side effects, such as dryness of mouth and urinary retention (especially in males), of the antihistamines. If these side effects occur and continue or are severe, medication should probably be discontinued. /Antihistamines/|Some patients, especially children, receiving antihistamines may experience paradoxical excitement characterized by restlessness, insomnia, tremors, euphoria, nervousness, delirium, palpitation, and even seizures. /Antihistamine drugs/|For more Populations at Special Risk (Complete) data for BROMPHENIRAMINE (8 total), please visit the HSDB record page.
Drug Information
For the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing.
Brompheniramine and chlorpheniramine maleate are first generation antihistamines that are widely used to treat symptoms of allergic rhinitis and the common cold. Clinically apparent liver injury from brompheniramine or chlorpheniramine must be exceeding rare, if it occurs at all.
Antihistamines
Anti-Allergic Agents; Histamine H1 Antagonists|Brompheniramine and dexbrompheniramine share the actions and uses of other antihistamines. Preparations containing brompheniramine maleate or dexbrompheniramine maleate in fixed combination with other agents (e.g., dextromethorphan, guaifenesin, phenylephrine, pseudoephedrine) are used for relief of rhinorrhea, sneezing, lacrimation, itching eyes, oronasopharyngeal itching, and/or other symptoms (e.g., nasal/sinus congestion, cough) associated with seasonal (e.g., hay fever) or perennial (nonseasonal) allergic rhinitis, nonallergic (vasomotor) rhinitis, other upper respiratory allergies, or the common cold. Combination preparations generally should only be used when symptoms amenable to each ingredient are present concurrently.
Like other antihistamines, brompheniramine and dexbrompheniramine should not be used in premature or full-term neonates. Conventional or extended-release preparations of brompheniramine maleate should be used in children younger than 2 or 6 years of age, respectively, only under the direction of a clinician. Brompheniramine maleate should not be used for self-medication in children younger than 6 years of age.|Overdosage and toxicity (including death) have been reported in children younger than 2 years of age receiving nonprescription (over-the-counter, OTC) preparations containing antihistamines, cough suppressants, expectorants, and nasal decongestants alone or in combination for relief of symptoms of upper respiratory tract infection. There is limited evidence of efficacy for these preparations in this age group, and appropriate dosages (i.e., approved by the US Food and Drug Administration (FDA)) for the symptomatic treatment of cold and cough have not been established. Therefore, FDA stated that nonprescription cough and cold preparations should not be used in children younger than 2 years of age; the agency continues to assess safety and efficacy of these preparations in older children. Meanwhile, because children 2-3 years of age also are at increased risk of overdosage and toxicity, some manufacturers of oral nonprescription cough and cold preparations recently have agreed to voluntarily revise the product labeling to state that such preparations should not be used in children younger than 4 years of age. Because FDA does not typically request removal of products with previous labeling from pharmacy shelves during a voluntary label change, some preparations will have the new recommendation ("do not use in children younger than 4 years of age"), while others will have the previous recommendation ("do not use in children younger than 2 years of age"). FDA recommends that parents and caregivers adhere to the dosage instructions and warnings on the product labeling that accompanies the preparation if administering to children and consult with their clinician about any concerns. Clinicians should ask caregivers about use of nonprescription cough and cold preparations to avoid overdosage.|Some patients, especially children, receiving antihistamines may experience paradoxical excitement characterized by restlessness, insomnia, tremors, euphoria, nervousness, delirium, palpitation, and even seizures. /Antihistamine drugs/|Adverse effects, which vary in incidence and severity with the individual drug, are caused by all antihistamines, although serious toxicity rarely occurs. Individual patients vary in their susceptibility to the adverse effects of these drugs, and such effects may disappear despite continued therapy. Geriatric patients may be particularly susceptible to dizziness, sedation, and hypotension. Most mild reactions may be relieved by a reduction in dosage or changing to another antihistamine. /Antihistamine drugs/|For more Drug Warnings (Complete) data for BROMPHENIRAMINE (17 total), please visit the HSDB record page.
/CASE REPORTS/ The case history and toxicological findings of an infant fatality involving pseudoephedrine, brompheniramine, and dextromethorphan are presented. Concentrations of brompheniramine ... measured in both postmortem blood and liver /was/ .... 0.40 mg/L in blood and 0.16 mg/kg in liver. ...|There is limited information about toxic and lethal concentrations of ... /antihistamines/ in children. .... a case of a pediatric fatality due to a common brompheniramine and phenylpropanolamine preparation /is presented/ and .... available Pediatric Toxicology Registry data on alkylamine antihistamines /were reviewed/. ... A review of the Registry data suggests that postmortem blood brompheniramine concentrations of 0.4 mg/L and greater in children is indicative of brompheniramine poisoning. ...
Brompheniramine is an antihistaminergic medication of the propylamine class. It is a first-generation antihistamine. In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Brompheniramine is a histamine H1 antagonist (or more correctly, an inverse histamine agonist) of the alkylamine class. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)|Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)
Antihistamines are well absorbed from the gastrointestinal tract after oral administration.|Brompheniramine and dexbrompheniramine maleates appear to be well absorbed from the GI tract.|Distribution of brompheniramine into human body tissues and fluids has not been fully characterized, but the drug appears to be widely distributed. Following oral administration of a single dose of the drug in healthy adults, the apparent volume of distribution reportedly averaged 11.7 L/kg.|Following oral administration of a single 0.13-mg/kg dose of brompheniramine maleate in healthy, fasting adults in one study, peak serum brompheniramine concentrations of 7.7-15.7 ng/mL occurred within 2-5 hours; in most of these individuals, a second lower peak, possibly secondary to enterohepatic circulation, also was observed. The antihistamine effect of brompheniramine, as determined by suppression of the wheal and flare responses induced by intradermal administration of histamine, appears to be maximal within 3-9 hours after a single oral dose of the drug, but suppression of the flare response may persist for up to at least 48 hours; the antipruritic effect appears to be maximal within 9-24 hours.|Brompheniramine and its metabolites are excreted principally in urine. About 40% of an oral dose of brompheniramine is excreted in urine and about 2% in feces within 72 hours in healthy individuals. In healthy individuals, about 5-10% of an oral dose is excreted in urine as unchanged drug ... .|The pharmacokinetics and antihistaminic effect of brompheniramine in seven normal adults /were assessed/. The mean peak serum brompheniramine concentration of 11.6 +/- 3.0 ng/mL occurred at a mean time of 3.1 +/- 1.1 hr. The mean serum half-life value was 24.9 +/- 9.3 hr, the mean clearance rate was 6.0 +/- 2.3 mL/min/kg, and the mean volume of distribution was 11.7 +/- 3.1 L/kg. The mean wheal size was significantly suppressed (P less than or equal to 0.1) at 3, 6, and 9 hr after the brompheniramine dose when mean concentrations ranged from 10.2 +/- 2.9 to 7.0 +/- 2.2 ng/mL. Significant suppression (P less than or equal to 0.05) of mean flare size was found from 3 to 48 hr after the brompheniramine dose, when mean concentrations ranged from 10.2 +/- 2.9 to 2.5 +/- 0.6 nL/mL. The mean pruritus score was significantly suppressed at 9 and 12 hr (P less than or equal to 0.1) and at 24 hr (P less than or equal to 0.05). Brompheniramine had a long half-life and large volume of distribution in normal adults. It also had a prolonged antihistaminic effect in the skin as evidenced by suppression of the wheal and flare response to histamine and by suppression of pruritus.
Hepatic (cytochrome P-450 system), some renal.|The metabolic and excretory fate of the drug has not been fully characterized. Brompheniramine undergoes N-dealkylation to form monodesmethylbrompheniramine and didesmethylbrompheniramine, and is metabolized to the propionic acid derivative, which is partially conjugated with glycine, and to other unidentified metabolites. Brompheniramine and its metabolites are excreted principally in urine. About 40% of an oral dose of brompheniramine is excreted in urine and about 2% in feces within 72 hours in healthy individuals. In healthy individuals, about 5-10% of an oral dose is excreted in urine as unchanged drug, 6-10% as monodesmethylbrompheniramine, 6-10% as didesmethylbrompheniramine, small amounts as the propionic acid derivative and its glycine conjugate, and the remainder as unidentified metabolites.
the pharmacokinetics and antihistaminic effect of brompheniramine in seven normal adults /were assessed/. ... The mean serum half-life value was 24.9 +/- 9.3 hr ...|In healthy adults, the half-life of brompheniramine reportedly ranges from 11.8-34.7 hours.
Brompheniramine is an antagonist of the H1 histamine receptors with moderate antimuscarinic actions, as with other common antihistamines such as diphenhydramine. Due to its anticholindergic effects, brompheniramine may cause drowsiness, sedation, dry mouth, dry throat, blurred vision, and increased heart rate.|H1 antagonists inhibit most of the effects of histamine on smooth muscles, especially the constriction of respiratory smooth muscle. /Histamine Antagonists: H1 Antagonists/|H1 antagonists strongly block the increased capillary permeability and formation of edema and wheal brought about by histamine. /Histamine Antagonists: H1 Antagonists/|Antihistamines competitively antagonize most of the smooth muscle stimulating actions of histamine on the H1-receptors of the GI tract, uterus, large blood vessels, and bronchial muscle. Contraction of the sphincter of Oddi and bile duct may be mediated in part by H1-receptors, and opiate-induced contraction of biliary smooth muscle has been antagonized by antihistamines. The drugs only are feebly antagonistic to bronchospasm induced by antigen-antibody reactions. Antihistamines also effectively antagonize the action of histamine that results in increased capillary permeability and the formation of edema. H1-receptor antagonists also suppress flare and pruritus that accompany the endogenous release of histamine. Antihistamines appear to act by blocking H1-receptor sites, thereby preventing the action of histamine on the cell; they do not chemically inactivate or physiologically antagonize histamine nor do they prevent the release of histamine. Antihistamines do not block the stimulating effect of histamine on gastric acid secretion, which is mediated by H2-receptors of the parietal cells. /Antihistamine drugs/|... Affinities of two commonly used over-the-counter antihistamines, brompheniramine and chlorpheniramine, as well as terfenadine in comparison with atropine at the five human muscarinic cholinergic receptor subtypes using CHO cells stably transfected with the individual subtypes /were evaluated/. Atropine was more potent than all three drugs at m1-m5 (p<0.01). No significant difference was observed between chlorpheniramine and brompheniramine. Atropine, brompheniramine, and chlorpheniramine could not discriminate between m1-m5. ...
Emergency and supportive measures: Maintain an open airway and assist ventilation if necessary. Treat coma, seizures, hyperthermia, and atypical ventricular tachycardia if they occur. Monitor the patient for at least 6 to 8 hours after ingestion. Specific drugs and antidotes: There is no specific antidote for antihistamine overdose. As for anticholinergic poisoning, physostigmine has been used for treatment of severe delirium or tachycardia. However because antihistamine overdose carry a greater risk for seizures physostigmine is not recommended routinely. Sodium bicarbonate may be useful for myocardial depression ... . Decontamination: Administer activated charcoal orally if conditions are appropriate. Gastric lavage is not necessary after small to moderate ingestions if activated charcoal can be given promptly. Because of slowed gastrointestinal motility, gut decontamination procedures may be helpful even in late-presenting patients. Enhanced elimination: Hemodialysis, hemoperfusion, peritoneal dialysis, and repeat dose activated charcoal are not effective in removing antihistamines. /Antihistamines/|/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/
/SIGNS AND SYMPTOMS/ In acute poisoning with H1 antagonists, their central excitatory effects constitute the greatest danger. The syndrome includes hallucinations, excitement, ataxia, incoordination, athetosis, and convulsions. Fixed, dilated pupils with a flushed face, together with sinus tachycardia, urinary retention, dry mouth, and fever, lend the syndrome a remarkable similarity to that of atropine poisoning. Terminally, there is deepening coma with cardiorespiratory collapse and death, usuallY within 2 to 18 hours. Treatment is along general symptomatic and supportive lines. /Histamine Antagonists: H1 Antagonists/|/SIGNS AND SYMPTOMS/ Symptoms of antihistamine toxicity in children may resemble atropine overdosage and include fixed dilated pupils, abnormal eye movements, flushed face, dry mouth, urinary retention, fever, excitation, hallucinations, disorientation, delusions, agitation, bizarre behavior, confusion, jitteriness, restlessness, irritability, hyperactivity, delirium, twitching, tiredness, abnormal tongue movement, unsteady gait, trembling extremities, slurred speech, ataxia, incoordination, athetosis, tonic-clonic seizures, and postictal depression.|/CASE REPORTS/ The case history and toxicological findings of an infant fatality involving pseudoephedrine, brompheniramine, and dextromethorphan are presented. Concentrations of brompheniramine and dextromethorphan were measured in both postmortem blood and liver specimens using a gas chromatograph equipped with a nitrogen-phosphorus detector. Brompheniramine and dextromethorphan were 0.40 mg/L and 0.50 mg/L, respectively, in the blood sample and 0.16 mg/kg and 0.57 mg/kg in the liver sample. The concentration of pseudoephedrine in blood and liver specimens was measured using gas chromatography-mass spectrometry and was determined to be 14.4 mg/L in the blood and 16 mg/kg in the liver. Additionally, a baby bottle allegedly administered to the infant was collected as evidence and sent to the Medical Examiner's Office for evaluation. The amounts of total brompheniramine, dextromethorphan, and pseudoephedrine remaining in the baby bottle were 1.4 mg, 9.4 mg, and 40 mg, respectively.|/CASE REPORTS/ The Montgomery County Coroner's Office has encountered a series of 10 infant deaths over an 8-month period in infants under 12 months old with toxicology findings that include a variety of drugs commonly found in over-the-counter (OTC) cold medications. The drugs detected were ephedrine, pseudoephedrine, dextromethorphan, diphenhydramine, chlorpheniramine, brompheniramine, ethanol, carbinoxamine, levorphanol, acetaminophen, and the anti-emetic metoclopramide. Toxicology findings were confirmed in 2 different matrices in 9 of the 10 cases and by 2 different analytical methods. The blood concentrations of the drugs and the case histories, as well as the cause of death for each infant, if available, will be given. The majority of these deaths were either toxicity from the OTC cold medications directly or as a contributory factor in the cause of death. Only two of the cases were the result of possible child abuse. Caregivers may be under the mistaken notion that OTC cold medications formulated for children are also safe for use in infants. These cases demonstrate that not only is administration of some OTC cold medications not safe, but use of OTC cold medications in infants can result in toxicity that can lead to death.|/CASE REPORTS/ ... The Civil Aerospace Medical Institute's (CAMI's) Toxicology Database was examined for the presence of the first-generation antihistamines in pilot fatalities of civil aircraft accidents that occurred during a 16-yr (1990-2005) period. Of 5383 fatal aviation accidents from which CAMI received specimens, there were 338 accidents wherein pilot fatalities (cases) were found to contain brompheniramine, chlorpheniramine, diphenhydramine, doxylamine, pheniramine, phenyltoloxamine, promethazine, and triprolidine. Of the 338 accidents, 304 were general aviation accidents, and 175 of the 338 pilots held private pilot airman certificates. Antihistamines were detected alone in 103 fatalities (1 antihistamine in 94 and 2 antihistamines in 9), while other drug(s) and/or ethanol were also present in an additional 235 fatalities. The antihistamines were found in approximately 4 and 11% of the fatalities/accidents in 1990 and in 2004, respectively. The use of antihistamine(s) was determined by the National Transportation Safety Board to be the cause of 13 and a factor in 50 of the 338 accidents. There was an overall increasing trend in the use of antihistamines by aviators during the 16-yr span. Blood levels of the antihistaminics were in the sub-therapeutic to toxic range.
Brompheniramine
(±)-Brompheniramine Use and Manufacturing
REACTION OF ALPHA-(P-BROMOPHENYL)-2-PYRIDINE-ACETONITRILE WITH SODAMIDE FOLLOWED BY CONDENSATION WITH 2-CHLORO-N,N-DIMETHYLETHYLAMINE, CONVERSION TO THE CORRESPONDING ACID, AND DECARBOXYLATION BY TREATMENT WITH SULFURIC ACID|ALPHA-(P-BROMOPHENYL)-2-PYRIDINE-ACETONITRILE IS CONVERTED TO ITS SODIUM DERIV.../WHICH/ IS...CONDENSED WITH 2-CHLORO-N,N-DIMETHYLETHYLAMINE. RESULTING NITRILE...CONVERTED TO ITS CORRESPONDING ACID.../&/ DECARBOXYLATED... MIXT /MADE/ ALKALINE, BROMPHENIRAMINE BASE...EXTRACTED & REACTED WITH...MALEIC ACID. /MALEATE/|Preparation from alpha-(p-bromophenyl)-alpha-(beta-dimethylaminoethyl)-2-pyridylacetonitrile: Sperber et al., US 2567245 (1951); US 2676964 (1954 to Schering).
antidepressant
(1977) PROBABLY MORE THAN 9.08X10+5 G-MALEATE|(1979) PROBABLY MORE THAN 9.08X10+5 G-MALEATE
ESSENTIALLY 100% AS AN ANTIHISTAMINE (AS MALEATE)
Alacol DM syrup/Brompheniramine maleate/|Anaplex DMX cough syrup; HD cough syrup /Brompheiramine maleate/|Bromfed-DM syrup /Brompheniramine maleate; Dextromethorphan hydrobromide; Pseudophedrine hydrochloride/|Dimetapp elixir, oral: 2 mg/5 mL; 12.5 mg/5 mL; Extended release, oral: 12 mg; 75 mg.. /Brompheniramine maleate; Phenylpropanolamine hydrochloride/ /former/|For more Formulations/Preparations (Complete) data for BROMPHENIRAMINE (7 total), please visit the HSDB record page.
2-Pyridinepropanamine, .gamma.-(4-bromophenyl)-N,N-dimethyl-: INACTIVE
Analyte: brompheniramine maleate; matrix: general sample; procedure: thin-layer chromatography /brompheniramine maleate/|Analyte: brompheniramine maleate; procedure: gas-liquid chromatography /brompheniramine maleate/|Analyte: brompheniramine maleate; matrix: pharmaceutical preparation; procedure: high-pressure liquid chromatography /brompheniramine maleate/|Analyte: brompheniramine; matrix: pharmaceutical preparation (tablet), urine; procedure: high-performance liquid chromatography with chemiluminescence detection; limit of detection: 140 ng/mL|For more Analytic Laboratory Methods (Complete) data for BROMPHENIRAMINE (16 total), please visit the HSDB record page.
Analyte: brompheniramine maleate; matrix: blood, urine; procedure: gas chromatography /brompheniramine maleate/|Analyte: brompheniramine; matrix: blood (plasma), urine; procedure: capillary zone electrophoresis with ultraviolet detection at 214 nm|Analyte: brompheniramine; matrix: blood (serum); procedure: high-performance liquid chromatography with ultraviolet detection at 254 nm; limit of detection: 2 ng/mL|Analyte: brompheniramine; matrix: blood (plasma, whole); procedure: high-performance liquid chromatography with diode array detection and ultraviolet detection at 226 nm; limit of detection: <120 ng/mL|For more Clinical Laboratory Methods (Complete) data for BROMPHENIRAMINE (7 total), please visit the HSDB record page.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:319.24
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:318.07316
Monoisotopic Mass:318.07316
Topological Polar Surface Area:16.1
Heavy Atom Count:19
Complexity:249
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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