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Home > Encyclopedia > (±)-Tetrahydrozoline

(±)-Tetrahydrozoline

(±)-Tetrahydrozoline structure

(±)-Tetrahydrozoline 

structure
  • CAS No:

    84-22-0

  • Formula:

    C13H16N2

  • Chemical Name:

    (±)-Tetrahydrozoline

  • Synonyms:

    1H-Imidazole,4,5-dihydro-2-(1,2,3,4-tetrahydro-1-naphthalenyl)-;2-Imidazoline,2-(1,2,3,4-tetrahydro-1-naphthyl)-;4,5-Dihydro-2-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazole;2-(1,2,3,4-Tetrahydro-1-naphthyl)-2-imidazoline;Tetrahydrozoline;Tetryzoline;Tetryzolin;dl-Tetrahydrozoline;(±)-Tetrahydrozoline;Ocuzolin;Tetryvil;2-(1,2,3,4-Tetrahydronaphthalen-1-yl)-4,5-dihydro-1H-imidazole;67731-52-6

  • Categories:

    Active Pharmaceutical Ingredients  >  Nervous System Drugs

Description

Tetryzoline is a member of imidazolines and a carboxamidine. It has a role as a sympathomimetic agent and a nasal decongestant. It is a conjugate base of a tetryzoline(1+).|Tetryzoline (also known as Tetrahydrozoline), a derivative of imidazoline, is found in over-the-counter eye drops and nasal sprays. Other derivatives include naphazoline, oxymetazoline, and xylometazoline. Johnson and Johnson manufactures tetryzoline eye drops under the brand Visine ®.

(±)-Tetrahydrozoline Basic Attributes

200.28

200.28

201-522-3

P7M4KML3S8

DTXSID1047861

S01GA02|R - Respiratory system|S - Sensory organs

Characteristics

24.4

3.69 (est)

1.2 g/cm3

117-119 °C @ Solvent: Heptane, Ethanol

393.5ºC at 760 mmHg

191.8ºC

1.656

In water, 3.1X10+1 mg/L at 25 deg C (est)

Tetrahydrozoline hydrochloride nasal and ophthalmic solutions should be stored in tight containers.

6.5X10-7 mm Hg at 25 deg C (est)

Henry's Law constant = 4.44X10-8 atm-cu m/mol at 25 °C (est)

pKa = 10.17 (est)|pKa = 10.92 (tertiary imidazoline nitrogen) (est)

Mol wt 236.75. Crystals from alcohol, decomposes at 256-257 °C. UV max: 264.5, 271.5 nm (A 1% 1cm = 17.5, 15.5). Freely soluble in water, alcohol. Very slightly soluble in chloroform. Practically insoluble in ether. pH of a 1% aqueous solution: 5.0 to 6.5. /Tetrahydrozoline hydrochloride/|Hydroxyl radical reaction rate constant = 8.33X10-11 cu cm/molecule-sec at 25 °C (est)

Safety Information

Commercial products stored up to 3 yr at room temperature demonstrated no significant degradation.

P264, P270, P301+P312, P330, P501

H302

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product. /Tetrahydrozoline hydrochloride/

Ophthalmic vasoconstrictors. The active ingredient of the product consists of one of the following, within the established concentration for each ingredient: Tetrahydrozoline hydrochloride, 0.01 to 0.05 percent. /Tetrahydrozoline hydrochloride/|The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including tetrahydrozoline hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Tetrahydrozoline hydrochloride/

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). /Tetrahydrozoline hydrochloride/|Skin protection: Handle with gloves. /Tetrahydrozoline hydrochloride/|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. /Tetrahydrozoline hydrochloride/|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). /Tetrahydrozoline hydrochloride/

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. /Tetrahydrozoline hydrochloride/|Advice for firefighters: Wear self-contained breathing apparatus for fire fighting if necessary. /Tetrahydrozoline hydrochloride/

Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx), hydrogen chloride gas. /Tetrahydrozoline hydrochloride/

ACCIDENT RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal. /Tetrahydrozoline hydrochloride/

ACCIDENT RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. /Tetrahydrozoline hydrochloride/|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection. /Tetrahydrozoline hydrochloride/|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. /Tetrahydrozoline hydrochloride/|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. /Tetrahydrozoline hydrochloride/|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Toxicity

Reports of prolonged cardiovascular effects after unintentional ingestion of tetrahydrozoline are noted in the literature.|IDENTIFICATION AND USE: Tetrahydrozoline hydrochloride, an imidazoline derivative, is applied topically to the eye for self-medication to temporarily relieve congestion, itching, and minor irritation, and to control hyperemia in patients with superficial corneal vascularity. Ocular decongestants are ineffective in the treatment of delayed hypersensitivity reactions such as contact dermatoconjunctivitis. The vasoconstrictor effect of tetrahydrozoline may be used during some ocular diagnostic procedures, but some clinicians prefer phenylephrine to tetrahydrozoline for this use. HUMAN STUDIES: Serious adverse events requiring hospitalization have been reported in pediatric patients following accidental ingestion of nonprescription ophthalmic solutions or nasal sprays containing imidazoline derivatives including tetrahydrozoline. Between 1985 and October 2012, 96 cases of accidental ingestion were reported in children 1 month to 5 years of age. The amount of drug ingested ranged from 0.6-45 mL. While no deaths were reported, more than half of these cases reported serious adverse events requiring hospitalization, including nausea, vomiting, lethargy, tachycardia, decreased respiration, bradycardia, hypotension, hypertension, sedation, somnolence, mydriasis, stupor, hypothermia, drooling, and coma. ANIMAL STUDIES: In dogs, signs of intoxication may include vomiting, bradycardia, cardiac arrhythmias, poor capillary refill time, hypotension or hypertension, panting, increased upper respiratory sounds, depression, weakness, nervousness, hyperactivity, or shaking. These signs appear within 30 min to 4 hr postexposure. In general, imidazoline decongestant exposure may affect the GI, cardiopulmonary, and nervous systems.

BACKGROUND: We report two cases of drug-facilitated sexual assault which presented with CNS depression rendering the victims vulnerable to sexual assault and unable to recall the events surrounding the crimes. In each tetrahydrozoline (THZ) was quantified. CASE REPORT: Case #1 ingested an unknown amount of eye drops containing THZ mixed with alcoholic beverages. Case #1 presented to the emergency department (ED) approximately 7 hr after reportedly being sexually assaulted and was without symptoms in the ED. Earlier reports from individuals who saw her indicated the victim to be "heavily intoxicated". Case #2 also ingested an unknown amount of eye drops containing THZ mixed with alcoholic beverages. Case #2 presented to an ED without symptoms approximately 23 hr after reportedly being sexually assaulted. Urine obtained from both cases was assessed for THZ concentrations using gas-chromatography-mass spectrometry. CASE DISCUSSION: Case #1 had a 0.15 g% (by weight by volume) urine ethanol concentration and a urinary THZ concentration of 1.481 ng/mL, approximately 7h after ingestion. Case #2 was negative for ethanol but had a urine THZ concentration of 108 ng/mL at 23 hr post-ingestion. Few case reports have been published documenting the use of THZ to facilitate sexual assault. CONCLUSION: We report two cases of drug-facilitated sexual assault involving the use of THZ where alcoholic beverages were concomitantly consumed. This is the first paper to our knowledge which discusses pharmacology of THZ ingestion and the significance of alcohol being present.

Patients with glaucoma should be advised not to use tetrahydrozoline ophthalmic solutions except under the advice and supervision of a physician. Ophthalmic solutions of the drug should not be used in patients with angle-closure glaucoma or other serious eye diseases.|Tetrahydrozoline hydrochloride is contraindicated in children younger than 2 years of age. Ophthalmic solutions of tetrahydrozoline should not be used for self-medication in children younger than 6 years of age.

Tetrahydrozoline's production and administration as a vasoconstrictor and nasal decongestant(1) may result in its release to the environment through various waste streams(SRC).

Drug Information

For temporary relief of discomfort and redness of the eye due to minor eye irritations.|FDA Label

Ophthalmic Solutions; Sympathomimetics; Nasal Decongestants|/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Tetrahydrozoline is included in the database.|For the relief of redness of the eye due to minor eye irritations. /Included in US product label/|Tetrahydrozoline hydrochloride is applied topically to the conjunctiva for self-medication to temporarily relieve congestion, itching, and minor irritation, and to control hyperemia in patients with superficial corneal vascularity. Ocular decongestants are ineffective in the treatment of delayed hypersensitivity reactions such as contact dermatoconjunctivitis. The vasoconstrictor effect of tetrahydrozoline may be used during some ocular diagnostic procedures, but some clinicians prefer phenylephrine to tetrahydrozoline for this use.|For more Therapeutic Uses (Complete) data for Tetrahydrozoline (6 total), please visit the HSDB record page.

Excessive dosage and/or prolonged or too frequent use of tetrahydrozoline should be avoided. In children, excessive dosage of the drug may cause severe drowsiness accompanied by profuse sweating.|Ophthalmic use of tetrahydrozoline occasionally may cause systemic sympathomimetic effects such as headache, hypertension, weakness, sweating, palpitation, and tremors. Overdosage of the drug may produce CNS depression with drowsiness, decreased body temperature, bradycardia, shock-like hypotension, apnea, and coma. In pediatric patients, accidental ingestion of imidazoline derivatives (i.e., tetrahydrozoline, naphazoline, oxymetazoline) has resulted in serious adverse events requiring hospitalization (e.g., coma, bradycardia, decreased respiration, sedation, somnolence).|Tetrahydrozoline hydrochloride is contraindicated in children younger than 2 years of age. Ophthalmic solutions of tetrahydrozoline should not be used for self-medication in children younger than 6 years of age.|Use of tetrahydrozoline in the eye may cause blurred vision, irritation, and mydriasis. Conjunctival application of tetrahydrozoline, especially when high concentrations are used in geriatric patients, may liberate pigment granules, presumably from the iris. Rebound congestion, characterized by chronic redness, swelling, or reactive hyperemia, frequently occurs with prolonged use. Prolonged use of tetrahydrozoline ophthalmic solution should be avoided for these reasons.|For more Drug Warnings (Complete) data for Tetrahydrozoline (11 total), please visit the HSDB record page.

Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993) (See all compounds classified as Nasal Decongestants.)|Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)|Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS. (See all compounds classified as Ophthalmic Solutions.)

BACKGROUND: Major symptoms can occur from tetrahydrozoline (THZ) overdoses in young children, requiring intensive care management. We report three cases that presented with CNS depression and cardiovascular effects where serum concentrations were performed. CASE REPORT: Case 1 ingested an unknown amount of eye drops containing THZ, resulting in altered mental status, bradycardia, hypothermia, and hypotension. Cases 2 and 3 ingested 7.5 mL of eye drops containing THZ. Case 2 presented to the emergency department (ED) without symptoms but became lethargic and bradycardic 90 min after ingestion. By contrast, Case 3 became lethargic 15 min after ingestion and required intubation on arrival to the ED. All children were admitted to ICU for observation and improved within 24 hr of ingestion. Urine obtained for drug screening was positive for THZ. Blood was obtained to assess level using gas-chromatography mass-spectrometry (GC-MS). CASE DISCUSSION: Case 1 had plasma levels of 51.4 and 23.6 ng/mL at 7 and 12 hr, respectively, after ingestion, revealing a half-life of 4.4 hr. Numerous case reports have been published documenting the dangers of ingesting these topical over-the-counter (OTC) products. However, human PK data are not available to help in our understanding of THZ toxicokinetics and disposition in humans after ingestion. CONCLUSION: We report three pediatric cases after ingestion of THZ where plasma concentrations were obtained with a calculated half-life of 4.4 hr in one case.|INTRODUCTION: No information exists on therapeutic or toxic concentrations of tetrahydrozoline, which has been reported to be used in drug facilitated sexual assaults. The primary aim of this investigation was to establish baseline therapeutic serum and urine concentrations in a sample of healthy volunteers. METHODS: Ten healthy volunteers consented to have two drops of Original Visine eye drops (0.05% tetrahydrozoline solution) placed directly into the conjunctival sac of each eye, 30 seconds apart, at times 0, 4, 8, and 12 hr. Blood and urine samples were then collected at 2, 5, 9, 13, and 24 hr post-application and analyzed for concentrations. Tetrahydrozoline concentrations are described using measures of central tendency and dispersion at each time point, with predictions of serum and urine concentrations over time calculated using a linear mixed effects regression model. RESULTS: Tetrahydrazoline concentrations were detectable in both serum and urine after therapeutic ocular administration. The mean serum half-life of tetrahydrozoline was approximately 6 hr. Systemic absorption varied among subjects, with the maximum serum concentrations ranging from 0.068 to 0.380 ng/mL. At 24 hr, all patients had detectable urine concentrations of tetrahydrozoline (range = 13-210 ng/mL). CONCLUSION: When used as directed by the manufacturer for therapeutic ocular administration, tetrahydrozoline concentrations were detectable in both serum and urine up to 12 hr after the last administered dose. A concentration greatly exceeding the 95% confidence interval of drug present during therapeutic ocular use may be suggestive of illegal adulterant use or accidental or suicidal overdose.|Following topical application of tetrahydrozoline hydrochloride solutions to the conjunctiva, local vasoconstriction usually occurs within a few minutes and may persist for 4-8 hours. Occasionally, enough tetrahydrozoline may be absorbed to produce systemic effects. Information on the distribution and elimination of the drug in humans is not available.

... Ten healthy volunteers consented to have two drops of Original Visine eye drops (0.05% tetrahydrozoline solution) placed directly into the conjunctival sac of each eye, 30 seconds apart, at times 0, 4, 8, and 12 hr. Blood and urine samples were then collected at 2, 5, 9, 13, and 24 hr post-application and analyzed for concentrations. ... The mean serum half-life of tetrahydrozoline was approximately 6 hr. ...|/A child/ ingested an unknown amount of eye drops containing tetrahydrozoline (THZ) ... had plasma levels of 51.4 and 23.6 ng/mL at 7 and 12 hr, respectively, after ingestion, revealing a half-life of 4.4 hr. ...

Tetryzoline is an alpha-adrenergic agonist. Its primary action is the constriction of conjunctival blood vessels, which serves to decrease eye redness caused by minor ocular irritants.

/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 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 TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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 (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/|/VET:/ Decontamination may not be practical due to the rapid absorption and onset of clinical signs. Heart rate and rhythm and blood pressure should be assessed, and an ECG obtained if needed. IV fluids should be given, along with atropine ... , if bradycardia is present. Diazepam ... can be given if CNS signs (eg, apprehension, shaking) are present. Serum electrolytes (ie, potassium, sodium, chloride) should be assessed and corrected as needed. Yohimbine, which is a specific alpha2-adrenergic antagonist, can also be used ... if needed. If yohimbine is not available, atipamezole can be used ... . /Imidazoline decongestants/|For more Antidote and Emergency Treatment (Complete) data for Tetrahydrozoline (8 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ The mydriatic effect of three ocular decongestants, containing 0.1% tetrahydrozoline hydrochloride, 0.3% chlorpheniramine maleate, and 0.05% tetrahydrozoline hydrochloride in combination with 0.3% pheniramine maleate, respectively, was evaluated in 10 healthy volunteers. The study was carried out using a single dose of the tested drug, instilling 2 drops in one eye and 2 drops of a placebo in the other. The papillary diameters were measured by photographic pupillography under basal conditions and 15, 30, 45, 60, 90, and 120 min after each treatment. Near and distance visual acuity and tonometry were evaluated under basal conditions and 50 and 95 min after instillation of drugs. No statistical significant differences between the treated and the control pupil diameters were found after instillation of 0.1% tetrahydrozoline hydrochloride or 0.3% chlorpheniramine maleate. The combination of 0.05% tetrahydrozoline hydrochloride with 0.3% pheniramine maleate caused a significant mydriasis from 30 min up to 120 min (p < 0.01 and p < 0.0005) after instillation, more pronounced in light irides. No local and systemic effects and no effects on visual acuity and ocular pressure were detected. On the basis of our results, it is possible to conclude that the persistent mydriatric action of the two-drug combination is due to a synergism; the use of these eyedrops should be avoided in subjects with narrow-angle glaucoma, light irides, narrow iridocorneal angle, and low anterior chamber for the risk of ocular pressure increase.|/SIGNS AND SYMPTOMS/ The mechanism of action of tetrahydrozoline has not been conclusively determined. Most pharmacologists believe that the drug directly stimulates a-adrenergic receptors of the sympathetic nervous system and exerts little or no effect on beta-adrenergic receptors. Following topical application of tetrahydrozoline to the conjunctiva, small arterioles are constricted and conjunctival congestion is temporarily relieved, but reactive hyperemia may occur. The drug also may produce mydriasis when applied to the conjunctiva, but this effect is usually minimal with the concentrations used as ocular decongestants.|/SIGNS AND SYMPTOMS/ OBJECTIVES: To study acute exposure to imidazoline derivatives in 72 children younger than 15 years of age, followed-up from January 1994 to December 1999. METHODS: This is a retrospective study of 72 patients with age between 2 months and 13 years (median 2 years; 25-75% = 1 to 3 years old) exposed to naphazoline (N = 48), fenoxazoline (N = 18), oxymetazoline (N = 5) and tetrahydrozoline (N = 1), through oral (N = 46), nasal (N = 24) or unknown (N = 2) routes. RESULTS: Fifty-seven children developed clinical manifestations such as somnolence (N = 34/57), sweating (N = 20/57), pallor (N = 17/57), hypothermia (N = 16/57), bradycardia (N = 13/57), cool extremities (N = 9/57), restlessness (N = 7/57), tachycardia (N = 6/57), vomiting (N = 5/57), irregular respiratory pattern and apnea (N = 5/57), miosis/mydriasis (N = 4/57). Naphazoline was the active ingredient most frequently involved (N = 47), followed by fenoxazoline (N = 5) and oxymetazoline (N = 4). The onset of clinical manifestations was rapid, beginning within 2 hours after exposure in 32/57 children. Only supportive measures were employed, with one child requiring mechanical ventilation after accidental naphazoline ingestion. In most of the children resolution of symptoms occurred within 24 hours (N = 39/57). No deaths were observed. Patients exposed to naphazoline (N = 47/48) presented a higher frequency of clinical signs of poisoning in comparison with those exposed to fenoxazoline (N = 5/18) (p < 0.001). There were no significant differences in the frequency of patients who presented clinical manifestations considering the route of exposure [oral (N = 34/46), nasal (N = 21/24); p = 0.31]. CONCLUSIONS: Most children (especially those younger than 3 years) exposed to imidazoline derivatives (especially naphazoline) presented early signs of poisoning regardless of the exposure route (nasal or oral). The main signs observed were nervous system, cardiovascular and respiratory depression. Most children showed complete resolution of the symptoms within 24 hours.|/SIGNS AND SYMPTOMS/ Serious adverse events requiring hospitalization have been reported in pediatric patients following accidental ingestion of nonprescription (over-the-counter, OTC) ophthalmic solutions or nasal sprays containing imidazoline derivatives (i.e., tetrahydrozoline, naphazoline, oxymetazoline). Between 1985 and October 2012, 96 cases of accidental ingestion were reported in children 1 month to 5 years of age; the amount of drug ingested ranged from 0.6-45 mL. While no deaths were reported, more than half of these cases reported serious adverse events requiring hospitalization, including nausea, vomiting, lethargy, tachycardia, decreased respiration, bradycardia, hypotension, hypertension, sedation, somnolence, mydriasis, stupor, hypothermia, drooling, and coma.|For more Human Toxicity Excerpts (Complete) data for Tetrahydrozoline (15 total), please visit the HSDB record page.

2-(1,2,3,4-tetrahydro-1-naphthyl)-2-imidazoline

(±)-Tetrahydrozoline Use and Manufacturing

Methods of Manufacturing

Tetrahydrozoline ... is made by the condensation of 1,2,3,4-tetrahydro-1-naphthoic acid or its methyl ester with 1,2-ethylenediamine.|Preparation from ethylenediamine, ethylenediamine hydrochloride, and methyl 1,2,3,4-tetrahydro-1-naphthoate: Synerholm et al., United States of America patent 2731471 (1956 to Sahyun Labs.)

Uses

Ophthalmic Solutions; Sympathomimetics; Nasal Decongestants|MEDICATION

Table: Tetrahydrozoline Hydrochloride Preparations [Table#7142]|Table: Tetrahydrozoline Hydrochloride Combinations Preparations [Table#7143]

Analyte: tetrahydrozoline hydrochloride; matrix: chemical identification; procedure: infrared absorption spectrophotometry with comparison to standards /tetrahydrozoline hydrochloride/|Analyte: tetrahydrozoline hydrochloride; matrix: chemical identification; procedure: ultraviolet absorption spectrophotometry with comparison to standards /tetrahydrozoline hydrochloride/|Analyte: tetrahydrozoline hydrochloride; matrix: chemical identification; procedure: visual reaction (white, curdy precipitate) with silver nitrate (Chloride test) /tetrahydrozoline hydrochloride/|Analyte: tetrahydrozoline hydrochloride; matrix: chemical purity; procedure: dissolution in glacial acetic acid; addition of acetic anhydride, mercuric acetate and quinaldine red indicator; titration with perchloric acid /tetrahydrozoline hydrochloride/|For more Analytic Laboratory Methods (Complete) data for Tetrahydrozoline (12 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:200.28
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:200.131348519
Monoisotopic Mass:200.131348519
Topological Polar Surface Area:24.4
Heavy Atom Count:15
Complexity:259
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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