{{Short description|Chemical compound}} {{Drugbox | Watchedfields = changed | verifiedrevid = 464200398 | IUPAC_name = ''N'',''N''-Dimethyl-3-phenyl-3-pyridin-2-yl-propan-1-amine | image = Pheniramine.svg | image_class = skin-invert-image <!--Clinical data--> | tradename = | Drugs.com = {{drugs.com|international|pheniramine}} | MedlinePlus = | pregnancy_AU = A | pregnancy_US = C | legal_status = | routes_of_administration = Oral; injection (intramuscular or slow intravenous); topical (ophthalmic/nasal solution) <!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = Hepatic hydroxylation, demethylation and glucuronidation | elimination_half-life = 16 - 19 hrs (oral), 8 - 17 hrs (i.v.)<ref>{{cite journal | vauthors = Witte PU, Irmisch R, Hajdú P | title = Pharmacokinetics of pheniramine (Avil) and metabolites in healthy subjects after oral and intravenous administration | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 23 | issue = 1 | pages = 59–62 | date = January 1985 | pmid = 3988394 }}</ref> | excretion = Renal <!--Identifiers--> | IUPHAR_ligand = 7267 | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 86-21-5 | ATC_prefix = D04 | ATC_suffix = AA16 | ATC_supplemental = {{ATC|R06|AB05}} | PubChem = 4761 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01620 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4597 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 134FM9ZZ6M | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D08355 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1193 <!--Chemical data--> | C=16 | H=20 | N=2 | smiles = n1ccccc1C(c2ccccc2)CCN(C)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C16H20N2/c1-18(2)13-11-15(14-8-4-3-5-9-14)16-10-6-7-12-17-16/h3-10,12,15H,11,13H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = IJHNSHDBIRRJRN-UHFFFAOYSA-N }} <!-- Definition and medical uses --> '''Pheniramine''' (trade name '''Avil''' among others) is an antihistamine with anticholinergic properties used to treat allergic conditions such as hay fever or urticaria. It has relatively strong sedative effects, and may sometimes be used off-label as an over-the-counter sleeping pill in a similar manner to other sedating antihistamines such as diphenhydramine. Pheniramine is also commonly found in eyedrops used for the treatment of allergic conjunctivitis.
<!-- Society and culture --> It was patented in 1948.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=546 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA546 |language=en}}</ref> Pheniramine is generally sold in combination with other medications, rather than as a stand-alone drug, although some formulations are available containing pheniramine by itself.
==Side effects== Pheniramine may cause drowsiness or tachycardia, and over-dosage may lead to sleep disorders.{{Citation needed|date=January 2018}}
Overdose may lead to seizures, especially in combination with alcohol.{{Citation needed|date=January 2018}}
People combining with cortisol in the long term should avoid pheniramine as it may decrease levels of adrenaline (epinephrine) which may lead to loss of consciousness.{{Citation needed|date=January 2018}}
Pheniramine is a deliriant (hallucinogen) in toxic doses. Recreational use of Coricidin for the dissociative (hallucinogenic) effect of its dextromethorphan is hazardous because it also contains chlorpheniramine.{{Citation needed|date=January 2018}}
==Chemical relatives== Halogenation of pheniramine increases its potency 20-fold. Halogenated derivatives of pheniramine include chlorphenamine, brompheniramine, dexchlorpheniramine, dexbrompheniramine, and zimelidine. Two other halogenated derivatives, fluorpheniramine and iodopheniramine, are currently in use for research on combination therapies for malaria and some cancers. {{cn|date=August 2021}}
Other analogs include diphenhydramine, and doxylamine.
== Stereoisomerism == Pheniramine contains a stereocenter and can exists as either of two enantiomers. The pharmaceutical drug is a racemate, an equal mixture of the (''R'')- and (''S'')-forms.<ref name="Hager">{{cite book | vauthors = von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U | title = Hagers Handbuch der Pharmazeutischen Praxis | volume = Band 9: Stoffe P-Z | publisher = Springer Verlag | location = Berlin | edition = 5th | date = 2014 | page = 121 | isbn = 978-3-642-63389-8 }}</ref> {| class="wikitable" style="text-align:center" |- class="hintergrundfarbe6" ! colspan="2"| Enantiomers of pheniramine |- | class=skin-invert-image|180 px<br />(''R'')-Pheniramine<br><small> CAS number: 56141-72-1</small> | class=skin-invert-image|180 px<br />(''S'')-Pheniramine<br><small> CAS number: 23201-92-5</small> |}
==See also== *Development and discovery of SSRI drugs
==References== {{Reflist}}
==External links== *{{Commonscat-inline}} *{{MedlinePlusEncyclopedia|002529|Pheniramine overdose}} *[https://web.archive.org/web/20090806154413/http://www.racgp.org.au/cmi/swcavilt.pdf Leaflet on Avil] by The Royal Australian College of General Practitioners
{{Antihistamines}} {{Hypnotics and sedatives}} {{Hallucinogens}} {{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 = {{Histamine receptor modulators}} {{Monoamine reuptake inhibitors}} {{Muscarinic acetylcholine receptor modulators}} }}
Category:Dimethylamino compounds Category:Deliriants Category:H1 receptor antagonists Category:Muscarinic antagonists Category:2-Pyridyl compounds Category:Sanofi Category:Serotonin reuptake inhibitors Category:Over-the-counter drugs in the United States