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Chemical compound
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 .
It was patented in 1948.
[2] 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 ]
Overdose may lead to
seizures , especially in combination with alcohol.[
citation needed ]
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 ]
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 ]
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.[
citation needed ]
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.
[3]
Enantiomers of pheniramine
(R )-Pheniramine CAS number: 56141-72-1
(S )-Pheniramine CAS number: 23201-92-5
See also
References
^ Witte PU, Irmisch R, Hajdú P (January 1985). "Pharmacokinetics of pheniramine (Avil) and metabolites in healthy subjects after oral and intravenous administration". International Journal of Clinical Pharmacology, Therapy, and Toxicology . 23 (1): 59–62.
PMID
3988394 .
^ Fischer J, Ganellin CR (2006).
Analogue-based Drug Discovery . John Wiley & Sons. p. 546.
ISBN
9783527607495 .
^ von Bruchhausen F, Dannhardt G, Ebel S, Frahm AW, Hackenthal E, Holzgrabe U (2014). Hagers Handbuch der Pharmazeutischen Praxis . Vol. Band 9: Stoffe P-Z (5th ed.). Berlin: Springer Verlag. p. 121.
ISBN
978-3-642-63389-8 .
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