Molecule of the Month


This page was developed using Netscape 2.0 and HTML 2.0 and will probably require Netscape 2.0 to view it to best advantage. The "active" molecules will require Rasmol (Unix), RasWin 2.5 (PC) or RasMac 2.5 (Apple Mac) to view them in 3D ( to configure Netscape for helper programmes such as RasWin etc.) Alternatively clicking on the active graphics will allow you to download the Brookhaven PDB file the coordinates of which may be used within other molecular modelling packages such as Nemesis, Alchemy etc.
The cannabinoids are probably the oldest class of hallucinogenic compound known. They are found primarily in the plant family Cannabinaceae , which includes the source plant of hemp, currently finding a resurgence as a fashion fibre. The numerous names applied to crude cannabis include : bhang, charas, dagga, garija, hashish and more commonly pot. Only recently has major advances in molecular biology revealed some of the secrets of the sites of action of cannabis and in particular the cannabinoid known as delta 9-THC (tetrahydrocannabinol) a primary active principle. ..... (continued)

delta 9-THC

Chemically the cannabinoids are classed as terpenoid (terpene like) these compounds occur as essential oils within many plants and some are involved in vitamin, steroid and pigment formation.

The cannabinoids are fundamentally non-polar molecules, with low solubility in water, so they are normally self-administered by smoking. The volatilised fractions are inhaled as a vapour and a varying amount utilised depending on the smoking technique.

Biological effects of the cannabinoids include:

relaxation, floating sensation and depersonalisation (leading to out-of-body experiences), percetual changes (visual, auditory and tactile), slowing of time, loss of attention, euphoria and silliness.Comparisons may be made with alcohol and a debate about the two compound types usually leads to an interesting discussion, ultimately involving the subject of legalisation.

Apart from the trivial recreational uses/abuses aside, the cannabinoids find important medicinal use in the control of nausea (vomitting) induced by chemotherapy of cancer patients especially when toxic drugs are employed.


Notes:

the structure file was created using initial co-ordinates from the Chemical Databank Service Crystallographic (CSSR) database at Daresbury, UK and energy minimised within Nemesis (Oxford Molecular) software, saving as a Brookhaven PDB file format.


Further Reading for undergraduate students and above:
  1. Recent advances

    Mechoulam.R etal, Biochem.Pharmacol. 48, 1994, 1537-1544.

  2. For an interesting thread see

    Kolter.T and Sandhoff.K, Angew.Chem.Int.Ed.Engl, 1995, 34, 2363-4.


This Page is maintained by Dr Lee Banting of the University of Portsmouth. Page last updated: 28th March 1996.
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