Hemin

Hemin (haemin; ferric chloride heme) is an iron-containing porphyrin with chlorine that can be formed from a haem group, such as haem b found in the haemoglobin of human blood.

Hemin
Clinical data
AHFS/Drugs.comConsumer Drug Information
Pregnancy
category
  • US: C (Risk not ruled out)
    Routes of
    administration    		Intravenous infusion
    ATC code
    Legal status
    Legal status
    Identifiers
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    ECHA InfoCard100.036.475
    Chemical and physical data
    FormulaC34H32ClFeN4O4
    Molar mass651.94 g/mol g·mol−1
    3D model (JSmol)
     NY (what is this?)  (verify)

    Chemistry

    Hemin is protoporphyrin IX containing a ferric iron (Fe3+) ion with a coordinating chloride ligand.

    Chemically, hemin differs from the related heme-compound hematin chiefly in that the coordinating ion is a chloride ion in hemin, whereas the coordinating ion is a hydroxide ion in hematin.[1] The iron ion in haem is ferrous (Fe2+), whereas it is ferric (Fe3+) in both hemin and hematin.

    Hemin is endogenously produced in the human body, for example during the turnover of old red blood cells. It can form inappropriately as a result of hemolysis or vascular injury. Several proteins in human blood bind to hemin, such as hemopexin and serum albumin.

    Pharmacological use

    A lyophilised form of hemin is used as a pharmacological agent in certain cases for the treatment of porphyria attacks, particularly in acute intermittent porphyria. Administration of hemin can reduce haem deficits in such patients, thereby suppressing the activity of delta-amino-levulinic acid synthase (a key enzyme in the synthesis of the porphyrins) by biochemical feedback, which in turn reduces the production of porphyrins and of the toxic precursors of haem. In such pharmacological contexts, hemin is typically formulated with human albumin prior to administration by a medical professional, to reduce the risk of phlebitis and to stabilise the compound, which is potentially reactive if allowed to circulate in free-form. Such pharmacological forms of hemin are sold under a range of trade names including the trademarks Panhematin®[2] and Normosang®.[3]

    History of isolation

    Haemin was first crystallised out of blood in 1853, by Ludwik Karol Teichmann. Teichmann discovered that blood pigments can form microscopic crystals. Thus, crystals of hemin are occasional referred to as 'Teichmann crystals'. Hans Fischer synthesised haemin, for which he was awarded the Nobel Prize in Chemistry in 1930.[4] Fischer's procedure involves treating defribrinated blood with a solution of sodium chloride in acetic acid.[5]

    Forensics

    Hemin can be produced from haemoglobin by the so-called Teichmann test, when haemoglobin is heated with glacial acetic acid (saturated with saline). This can be used to detect blood traces.

    Other

    Hemin is considered the "X factor" required for the growth of Haemophilus influenzae.[6]

    See also

    References
    1. Grenoble DC and Drickamer HG (1968). ""The Effect of Pressure on the Oxidation State of Iron, III. Hemin and Hematin"" (PDF). Proceedings of the National Academy of Sciences USA. 61: 1177–1182. doi:10.1073/pnas.61.4.1177. PMC 225235.
    2. "Panhematin for Acute Porphyria". American Porphyria Foundation.
    3. "Normosang". Electronic Medicines Compendium (eMC).
    4. "Hans Fischer - Nobel Lecture - On haemin and the relationships between haemin and chlorophyll" (PDF). Nobel Prize Foundation.
    5. Hans Fischer (1941). "Hemin". Org. Synth. 21: 53. doi:10.15227/orgsyn.021.0053.
    6. Sherris, John C.; Ryan, Kenneth J.; Ray, C. L. (2004). Sherris medical microbiology: an introduction to infectious diseases. New York: McGraw-Hill. p. 395. ISBN 0-8385-8529-9.
    • Information from the American Porphyria Foundation, including emergency delivery information
    • Hemin at RxList
    • Hemin at the US National Library of Medicine Medical Subject Headings (MeSH)
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