Harmalol

Last updated
Harmalol
Harmalol structure.svg
Harmalol 3D BS.png
Names
Preferred IUPAC name
1-Methyl-4,9-dihydro-3H-pyrido[4,3-b]indol-7-ol
Other names
1-Methyl-4,9-dihydro-3H-β-carbolin-7-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.616 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-375-4
PubChem CID
UNII
  • InChI=1S/C12H12N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6,14-15H,4-5H2,1H3
    Key: RHVPEFQDYMMNSY-UHFFFAOYSA-N
  • OC1=CC=C(C(CCN=C3C)=C3N2)C2=C1
Properties
C12H12N2O
Molar mass 200.241 g·mol−1
AppearanceRed solid
Melting point 100 to 105 °C (212 to 221 °F; 373 to 378 K) (trihydrate) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Harmalol is a bioactive beta-carboline and a member of the harmala alkaloids. [2] [3]

Contents

Australia

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015). [4] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities. [4]

See also

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Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala, as well as tobacco leaves including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are both a reversible inhibitor of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.

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References

  1. Thieme Chemistry (Hrsg.): RÖMPP Online – Version 3.37. Georg Thieme Verlag KG, Stuttgart, 27. September 2013.
  2. Sarkar S, Bhadra K (2014). "Binding of alkaloid harmalol to DNA: photophysical and calorimetric approach". J Photochem Photobiol B. 130: 272–80. doi:10.1016/j.jphotobiol.2013.11.021. PMID   24368411.
  3. El Gendy MA, Soshilov AA, Denison MS, El-Kadi AO (2012). "Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms". Food Chem Toxicol. 50 (2): 353–62. doi:10.1016/j.fct.2011.10.052. PMC   3281145 . PMID   22037238.
  4. 1 2 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534