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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Infobox drug
| drug_name =
| INN =
| type =
| IUPAC_name = (''RS'')-2-(1,2,3,4-tetrahydronaphthalen-1-yl)-4,5-dihydro-1''H''-imidazole
| image = Tetrahydrozoline-2D-skeletal.svg
| alt =
| caption =
| Verifiedfields = changed
| verifiedrevid = 470604535

| pronounce =
| tradename =
| Drugs.com =
| MedlinePlus =
| pregnancy_AU = 
| pregnancy_AU_comment =
| pregnancy_US = 
| pregnancy_category=
| routes_of_administration =
| legal_AU = 
| legal_AU_comment =
| legal_BR = 
| legal_BR_comment =
| legal_CA = 
| legal_DE = 
| legal_NZ = 
| legal_UK = 
| legal_US = 
| legal_UN = 
| legal_status = 

| bioavailability =
| protein_bound =
| metabolism =
| metabolites =
| onset =
| elimination_half-life =
| duration_of_action =
| excretion =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5226
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08578
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1266
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H16N2/c1-2-6-11-10(4-1)5-3-7-12(11)13-14-8-9-15-13/h1-2,4,6,12H,3,5,7-9H2,(H,14,15)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BYJAVTDNIXVSPW-UHFFFAOYSA-N
| CAS_number = 84-22-0
| PubChem = 5419
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = S9U025Y077
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28674
| class =
| ATCvet =
| ATC_prefix = R01
| ATC_suffix = AA06
| ATC_supplemental = {{ATC|S01|GA02}}
| DrugBank =

| C=13|H=16|N=2
| SMILES = N\1=C(\NCC/1)C3c2ccccc2CCC3

| melting_point = 117-119
| melting_notes = <ref>{{Cite patent| country = US | number = 2731471 | inventor = Synerholm M, Jules LH, Sahyun M | title = Imidazoline Derivatives | gdate = 17 January 1956 | assign1 = Sahyun Laboratories | postscript = . }}</ref> {{convert|256|-|257|C|F}} for [[Hydrochloride|HCl]]-salt<ref name=":mer">{{Cite book | vauthors = Budavari S, O'Neil M, Smith A, Heckelman P, Obenchain J |title=The Merck Index | publisher = Chapman & Hall Electronic Publishing Division |year=2000 |edition= 12th |location=Whitehouse Station, NJ, United States |page=1453 |oclc=46987702 | isbn = 978-1-58488-129-2 }}</ref>
| solubility =Very soluble in water and ethanol, slightly soluble in chloroform and insoluble in diethylether<ref name=":mer" />
| sol_units =  
}}

'''Tetryzoline''' ([[International Nonproprietary Name|INN]]),<ref name=WHOINN/> also known as '''tetrahydrozoline''', is a drug used in some over-the-counter [[eye drop]]s and [[nasal spray]]s. Tetryzoline was patented in 1954, and came into medical use in 1959.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=978-3-527-60749-5 |page=552 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA552 |language=en}}</ref>

==Side effects==
Tetryzoline eye drops may cause blurred vision, eye irritation and [[dilated pupils]].<ref name=":0">{{Cite web|url=https://www.nlm.nih.gov/toxnet/index.html|title=Tetrahydrozoline|website=toxnet.nlm.nih.gov|archive-url=https://web.archive.org/web/20170103190214/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+7471|archive-date=2017-01-03|url-status=live|access-date=2018-09-05}}</ref> Tetryzoline is not suitable for prolonged use as its vasoconstrictive effects within the eye eventually decrease or stop. If tolerance to the drug has developed, ceasing its use may cause a rebound effect and ''increase'' redness of the eyes — ⁠a vasodilatory effect.<ref>{{cite journal | vauthors = McLaurin E, Cavet ME, Gomes PJ, Ciolino JB | title = Brimonidine Ophthalmic Solution 0.025% for Reduction of Ocular Redness: A Randomized Clinical Trial | journal = Optometry and Vision Science | volume = 95 | issue = 3 | pages = 264–271 | date = March 2018 | pmid = 29461408 | pmc = 5839712 | doi = 10.1097/OPX.0000000000001182 }}</ref>

Intranasal use of tetryzoline may cause transient burning, stinging, or dryness of the [[mucosa]] and sneezing. Prolonged intranasal use often causes opposite effects in the form of [[rebound congestion]] with effects such as chronic redness, swelling and [[rhinitis]]. Prolonged use thus may result in overuse of the drug.<ref name=":0" />

In children, it might cause profound sedation.<ref>{{Cite web |title=Tetryzoline |url=https://go.drugbank.com/drugs/DB06764 |access-date=2022-09-15 |website=go.drugbank.com}}</ref>

=== Overdose ===
Overdose most often causes [[slow heart rate]]. [[Respiratory depression]], [[low blood pressure]], [[constricted pupils]], [[hypothermia]], brief episodes of [[high blood pressure]],<ref name=":1">{{cite journal | vauthors = Al-Abri SA, Yang HS, Olson KR | title = Unintentional pediatric ophthalmic tetrahydrozoline ingestion: case files of the medical toxicology fellowship at the University of California, San Francisco | journal = Journal of Medical Toxicology | volume = 10 | issue = 4 | pages = 388–91 | date = December 2014 | pmid = 24760708 | pmc = 4252297 | doi = 10.1007/s13181-014-0400-9 }}</ref> drowsiness, headaches and vomiting may also occur.<ref name=":2" /> In serious cases some of these effects may result in [[circulatory shock]].<ref name=":0" /> Most often overdoses occur in children who have ingested the drug.<ref name=":1" />

There is no antidote for tetryzoline or other similar imidazoline analogue poisoning, but the [[Symptomatic treatment|symptoms can be alleviated]]. With treatment, death is rare.<ref name=":4">{{cite journal | vauthors = Carr ME, Engebretsen KM, Ho B, Anderson CP | title = Tetrahydrozoline (Visine®) concentrations in serum and urine during therapeutic ocular dosing: a necessary first step in determining an overdose | journal = Clinical Toxicology | volume = 49 | issue = 9 | pages = 810–4 | date = November 2011 | pmid = 21972870 | doi = 10.3109/15563650.2011.615064 | s2cid = 20238499 }}</ref>

== Pharmacology ==

=== Pharmacodynamics ===
Tetryzoline is an [[Alpha-adrenergic agonist|alpha agonist]] for the [[alpha-1 receptor|alpha-1]] and [[Alpha-2 adrenergic receptor|alpha-2 receptors]].<ref>{{Cite web |title=Tetryzoline |url=https://go.drugbank.com/drugs/DB06764 |access-date=2022-12-21 |website=go.drugbank.com}}</ref> This action relieves the redness of the eye caused by minor ocular irritants. Moreover, to treat [[allergic conjunctivitis]], tetryzoline can be combined in a solution with [[antazoline]].<ref name="Castillo">{{cite journal|vauthors=Castillo M, Scott NW, Mustafa MZ, Mustafa MS, Azuara-Blanco A|date=June 2015|title=Topical antihistamines and mast cell stabilisers for treating seasonal and perennial allergic conjunctivitis|url=http://aura.abdn.ac.uk/bitstream/2164/6048/1/Castillo_et_al_2015_The_Cochrane_Library.pdf|journal=The Cochrane Database of Systematic Reviews|volume=2015|issue=6|article-number=CD009566|doi=10.1002/14651858.CD009566.pub2|pmid=26028608|pmc=10616535 |hdl-access=free|hdl=2164/6048}}</ref>

=== Pharmacokinetics ===
In a healthy person, the [[biological half-life]] of tetryzoline is approximately 6 hours, and it is excreted in urine, chemically unchanged, at least in part. In one study, 10 people were given two drops of 0.5 mg/mL of tetryzoline eye drops (0.025–0.05 mg) at 0 hrs, 4 hrs, 8 hrs, and 12 hrs. Within a 24-hour time window, since the last dose of tetryzoline, the blood serum concentration of tetryzoline in the test subjects was 0.068-0.380 [[Nanogram|ng]]/mL and the urine concentration was 13–210 ng/mL. Both the blood and the urine levels of tetryzoline reached their maximums approximately 9 hrs after the last dose. These fluid-concentration levels correspond to normal ocular use of tetryzoline; thus, greater concentrations of tetryzoline in the blood and the urine of the user can indicate misuse of the drug or of poisoning with the drug.<ref name=":4" />

==Chemistry==
Chemically, tetryzoline is a [[derivative (chemistry)|derivative]] of [[2-Imidazoline|imidazoline]]. It has two [[enantiomers]].

==Society and culture==

===Names===
Tetryzoline is the International Nonproprietary Name (INN).<ref name=WHOINN>{{cite web|url=https://www.who.int/medicines/publications/druginformation/innlists/RL03.pdf|title=International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary Names: List 3|publisher=World Health Organization|page=474|archive-url=https://web.archive.org/web/20160911071542/http://www.who.int/medicines/publications/druginformation/innlists/RL03.pdf|archive-date=2016-09-11|url-status=live|access-date=30 August 2016}}</ref>

===Urban legend===
An [[urban legend]] suggests that tetryzoline can cause violent diarrhea if given orally, such as by putting a few drops of [[Visine]] in an unsuspecting person's beverage. However, the actual results of the prank may be worse, varying from severe nausea and vomiting to seizures or a coma. Larger doses can cause death. Diarrhea is not a side effect.<ref>{{cite web | title=Visine Prank: Mickey Red Eyes | url=http://www.snopes.com/medical/myths/visine.asp | work=Snopes | date=29 June 2009 | access-date=28 July 2010}}</ref>

===Criminal use===
In late August 2018, a [[South Carolina]] woman was charged with murdering her husband by putting eye drops containing tetryzoline in his drinking water. An autopsy found a high concentration of tetryzoline in his body.<ref>{{cite web | title=US wife accused of 'fatally poisoning husband with eyedrops' | url=https://www.bbc.com/news/world-us-canada-45411562 | work=BBC | date=4 September 2018 | access-date=4 September 2018}}</ref><ref>{{citation
|url=https://abcnews.go.com/US/wireStory/police-woman-kills-husband-putting-eye-drops-water-57539122
|title=Police: Woman kills husband by putting eye drops in water
|date=August 31, 2018
|publisher=Associated Press}}</ref><ref>{{cite news | vauthors = Connelly E |title=Wife admits fatally poisoning 'unfaithful' hubby with eye drops: cops |url=https://nypost.com/2018/09/01/wife-admits-fatally-poisoning-hubby-with-eye-drops-cops/ |access-date=3 September 2018 |publisher=New York Post |date=1 September 2018 |archive-url=https://web.archive.org/web/20180902012243/https://nypost.com/2018/09/01/wife-admits-fatally-poisoning-hubby-with-eye-drops-cops/ |archive-date=2018-09-02|url-status=live|language=en |format=Newspaper}}</ref>

Tetryzoline has been used as a [[date rape drug]] in a number of cases due to its ability to cause dizziness and unconsciousness.<ref name=":2">{{cite journal | vauthors = Stillwell ME, Saady JJ | title = Use of tetrahydrozoline for chemical submission | journal = Forensic Science International | volume = 221 | issue = 1–3 | pages = e12-6 | date = September 2012 | pmid = 22554870 | doi = 10.1016/j.forsciint.2012.04.004 }}</ref>

In 2018, a 62 year-old woman in [[Pewaukee, Wisconsin]], died in an apparent overdose or suicide involving tetryzoline and other substances; in November 2023 her caregiver was convicted of [[Murder in United States law#Degrees|first-degree murder]], following the allegation that her death was caused by a water bottle laced with [[Visine]].<ref>{{cite web | url = https://abcnews.go.com/US/wisconsin-woman-arrested-accused-murdering-friend-eye-drops/story?id=78148517 | title = Wisconsin woman arrested, accused of murdering friend with eye drops: An investigation alleges the victim's water bottle was laced with Visine. | work = ABC News | vauthors = Hutchinson B | date = 8 June 2021 }}</ref><ref>{{cite web |url=https://abcnews.go.com/US/wisconsin-woman-found-guilty-killing-friend-eye-drops/story?id=104887158 |title=Wisconsin woman found guilty of killing friend with eye drops |vauthors=Deliso M |work=[[ABC News (United States)|ABC News]] |date=14 November 2023}}</ref>

In 2019, a [[North Carolina]] paramedic was accused of using tetryzoline eye drops to cause the death of his wife. The blood sample results showed about 30–40 times higher than the therapeutic level of tetryzoline.<ref>{{Cite web | vauthors = Jacobo J, Stein B | date = 23 December 2019 |title=Paramedic accused of fatally poisoning his wife with ingredient found in eye drops: Prosecutors |url=https://abcnews.go.com/US/paramedic-accused-fatally-poisoning-wife-ingredient-found-eye/story?id=67883176 |access-date=2022-09-15 |website=ABC News |language=en}}</ref><ref>{{Cite web | vauthors = Lee BY |title=How Visine Eye Drops In The Mouth Can Kill, Here Are Two Cases |url=https://www.forbes.com/sites/brucelee/2020/01/18/how-visine-eye-drops-in-the-mouth-can-kill-here-are-two-cases/ |date=18 January 2020 |access-date=2022-09-15 |website=Forbes |language=en}}</ref>

==References==
{{Reflist}}

{{Adrenergic receptor modulators}}

[[Category:Alpha1-adrenergic agonists]]
[[Category:Alpha2-adrenergic agonists]]
[[Category:Imidazolines]]
[[Category:Tetralins]]
[[Category:Topical decongestants]]
[[Category:Vasoconstrictors]]

Tetryzoline - Revision history

imported>Blakegripling ph: /* Society and culture */ rmv pop culture cruft