IUPAC name
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;sulfuric acid;tetratriiodide
  • 7631-46-1
3D model (JSmol)
  • Interactive image
  • 4912094
ECHA InfoCard 100.028.677 Edit this at Wikidata
EC Number
  • 231-544-9
  • 6400556
  • FG2Z310P5U
  • InChI=1S/3C20H24N2O2.4I3.6H2O4S/c3*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;4*1-3-2;6*1-5(2,3)4/h3*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;;;;;6*(H2,1,2,3,4)/q;;;4*-1;;;;;;/t3*13-,14-,19-,20+;;;;;;;;;;/m000........../s1
  • COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O.I[I-]I.I[I-]I.I[I-]I.I[I-]I
Molar mass 3084.56 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Herapathite, or iodoquinine sulfate, is a chemical compound whose crystals are dichroic and thus can be used for polarizing light.

According to Edwin H. Land, it was discovered in 1852[1] by William Bird Herapath, a Bristol surgeon and chemist. One of his pupils found that adding iodine to the urine of a dog that had been fed quinine produced unusual green crystals. Herapath noticed while studying the crystals under a microscope that they appeared to polarize light.[2]

In the 1930s, Prof. Ferdinand Bernauer invented a process to grow single herapathite crystals large enough to be sandwiched between two sheets of glass to create a polarizing filter; these were sold under the Bernotar name by Carl Zeiss. Herapathite can be formed by precipitation by dissolving quinine sulphate in acetic acid and adding iodine tincture.[3]

Herapathite's dichroic properties came to the attention of Sir David Brewster, and were later used by Land in 1929 to construct the first type of Polaroid sheet polarizer. He did this by embedding herapathite crystals in a polymer instead of growing a single large crystal.


  1. ^ W. B. Herapath (1852). "XXVI. On the optical properties of a newly-discovered salt of quinine, which crystalline substance possesses the power of polarizing a ray of light, like tourmaline, and at certain angles of rotation of depolarizing it, like selenite". Phil. Mag. London: Taylor & Francis. 3 (17): 161–173. doi:10.1080/14786445208646983.
  2. ^ Kahr, Bart; Freudenthal, John; Phillips, Shane; Kaminsky, Werner (2009). "Herapathite". Science. 324 (5933): 1407. Bibcode:2009Sci...324.1407K. doi:10.1126/science.1173605. PMID 19520951. S2CID 220089099.
  3. ^ Gabba, Luigi (1884). Trattato Elementare di Chimica Inorganica ed Organica [Elementary Treatise on Inorganic and Organic Chemistry] (in Italian). Francesco Vallardi. p. 516.

Further readings

  • Bernauer, F. (1935). "Neue Wege zur Herstellung von Polarisatoren". Forschritte der Mineralogie, Kristallographie und Petrographie Neunzehnter Band.
  • Land, E.H. (1951). "Some aspects on the development of sheet polarizers". Journal of the Optical Society of America. 41 (12): 957–963. doi:10.1364/josa.41.000957.
  • Marks, A. M. (1969). "Electrooptical Characteristics of Dipole Suspensions". Applied Optics. 8 (7): 1397–1412. Bibcode:1969ApOpt...8.1397M. doi:10.1364/AO.8.001397. PMID 20072446.