Tetrahydrozoline

Tetrahydrozoline

Tetrahydrozoline
Identifiers
CAS number  N
PubChem
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
ATC code R01,S01
Jmol-3D images Image 1
Properties
Molecular formula C13H16N2
Molar mass 200.28 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Tetrahydrozoline (INN: Tetryzoline), a derivative of imidazoline, is found in over-the-counter eye drops and nasal sprays. Other derivatives include naphazoline, oxymetazoline, and xylometazoline.

Tetrahydrozoline is an alpha agonist and its main mechanism of action is the constriction of conjunctival blood vessels.[1] This serves to relieve the redness of the eye caused by minor ocular irritants.

An urban legend suggests that tetrahydrozoline can cause violent diarrhea if administered orally, such as by putting a few drops of Visine in an unsuspecting person's beverage. However, the actual results of the "Visine Prank" may be worse, varying from severe nausea and vomiting to seizures or a coma. Diarrhea is not a side effect.[2]

Chemistry

Tetrahydrozoline can be synthesized in one step by the heterocyclization of 1-cyanotetralin with ethylenediamine.[3]

References

  1. ^ Dahlström M, Lindgren F, Berntsson K et al. (July 2005). "Evidence for different pharmacological targets for imidazoline compounds inhibiting settlement of the barnacle Balanus improvisus". J. Exp. Zoolog. Part a Comp. Exp. Biol. 303 (7): 551–62.  
  2. ^ "Visine Prank: Mickey Red Eyes". Snopes. 29 June 2009. Retrieved 28 July 2010. 
  3. ^ M. E. Synerholm, L. H. Jules, M. Sahyun, U.S. Patent 2,731,471 (1956)