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Posted on: May 14, 2008 7:30 PM, by Molecule of the Day
Adamantane is a sort of triple-fused-cyclohexane structure:
I've previously covered its role as a functional group in a dermatological drug. The neatest thing about adamantane is that if you make polymers of it, you have carbons with four tetrahedral single bonds to other carbons, or a molecular diamond. Since part of why diamond is so unique is because it is in such a geometrically favored, fully valence-satisfied lattice, molecular diamonds are interesting in a lot of the ways diamonds are.
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Comments
More interesting still! Diamond has a negative work function into vacuum. So do diamondoid hydrocarbons. US Pat. 7160529
Google
diamondoid "field emission" 669 hits
Posted by: Uncle Al | May 14, 2008 8:20 PM
Is that a precursor for Wolverine's skeleton?
Posted by: jeb, FCD | May 14, 2008 11:26 PM
It's nice to draw adamantane like this, but if you make a space filling model you'll see that adamantane is quite spherical.
It is amusing that my undergraduate advisor (Paul Schleyer) subsequently had a lot to do with a synthesis for it, and that after I left organic chemistry and became a neurologist, I used a derivative (adamantine hydrochloride -- Symmetrel) as an adjunctive treatment for Parkinsonism. While the compound doesn't look anything like dopamine (the neurotransmitter deficient in Parkinson's disese), it causes dopamine release from neurons.
Coincidences like this are why I don't read novels. Life is far more fantastic.
Retread
Posted by: Retread | May 15, 2008 12:27 AM
Retread: I think you mean amantadine...though the two words are very similar. Amantadine is just amino adamantane, and is both an antiviral and a anti-parkonsinism drug.
Posted by: Vince Noir | May 16, 2008 5:39 PM
A million [censored] diamonds, Michael!
Posted by: aldehyde | May 19, 2008 7:42 PM
Vince Noir
You are quite right. Thanks
Posted by: retread | May 20, 2008 11:58 AM
Adamantane is in the stucture of these drugs:
- aminoadamantane (amantadine) hydrochloride - Symmetrel etc. (anti-Parkinson, antiviral - against bird flu)
- aminoadamantane (amantadine) sulphate (anti-Parkinson)
- memantine hydrochloride - Namenda (anti-Alzheimer)
- adapalele - 6-[3-(1-adamantyl)-4-methoxy-phenyl] naphthalene-2-carboxylic acid - Differin (acne treatment)
- Vildagliptin - (2S)-1-{2-[(3-hydroxy-1-adamantyl)amino]acetyl}
pyrrolidine-2-carbonitrile - this is new antidiabetic drug from Novartis, DPP4 inhibitor
- Saxagliptin - (1S,3S,5S)-2-[(2S)-2-amino-2-(3-hydroxy-1-adamantyl)
acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile - antidiabetic drug from Bristol-Myers
There are many other drugs with adamantane in the drug research or clinical trials ...
Posted by: Martin J. | May 27, 2008 2:33 PM
Allow me to contribute further Arrested Development props, as aldehyde did.
Posted by: Adam | June 5, 2008 2:37 AM
There is some really beat chemistry you can do with adamantane. You can for example brominate all the 4 apical carbons selectively in good yield under Friedel-Crafts like conditions. The carbocations are very stable and favors this reation. Then you can attach fuctionalized phenyl acetylenes to give large tetrahedral building blocks for porous materials and crystal egineering.
Posted by: Nanono | June 5, 2008 5:23 AM