Chemical Of The Week #1 - Carbidopa...and Introduction!

in introduceyourself •  6 years ago  (edited)

20190326_215928.jpg
3D model of Carbidopa

Hi,

I made this account to share cool information about some of the chemicals we use, and also teach people a few things about chemistry. I have always been fascinated by the pharmacology of Carbidopa, so it is my first entry! I hope you all enjoy it, and you can expect a post every week on an interesting chemical. I am open to suggestions! Please do not hesitate to ask questions too, I have a lot of background in chemistry and like explaining things in less convoluted ways!

Chemical Of The Week 1. Carbidopa

Chemical Identifier #. 34359
Empirical Formula: C10H14N2O4
Molecular Weight: 226.23
Synonyms: Lodosin, Lodosyn, Methyldopahydrazine, MK 485

Carbidopa is a drug used in the treatment of Parkinsons, usually in conjunction with Levodopa (aka L- Dopa). It functions by blocking the conversion of L-Dopa to Dopamine by Dopa decarboxylase. This may seem odd because you want more Dopamine in the brain. However it cannot cross the blood brain barrier, but L-dopa can, where it then is converted to Dopamine in the Substantia Nigra.

George Cotzias, a Greek-American scientist, is credited with the discovery of the ability of Carbidopas to increase the effectiveness of Parkinsons treatment with Levodopa. He also made the critical observation that Parkinsons symptoms decreased when Levodopa was administrated in increasing dosages over time.

Carbidopa became commercially available in 1975.

carbidopa.jpg
Line drawing structure of Carbidopa

References:

https://pubchem.ncbi.nlm.nih.gov/compound/carbidopa

https://www.ncbi.nlm.nih.gov/pubmed/9633679

https://medlineplus.gov/druginfo/meds/a601068.html

https://en.wikipedia.org/wiki/Carbidopa

George Cotzias
https://en.wikipedia.org/wiki/George_Cotzias

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Chemistry question:
Can acyl azides be prepared from carboxylic acids without activation of the carboxyl group (acyl chloride, anhydride, carbodiimide, active ester, etc.)? I’m preparing a precursor for Curtius rearrangement and hydrolysis to prepare the amine with one less C. (No other sensitive functional groups are present). Have you ever heard of cesium fluoride being used in this context? I know the best approach is to use DPPA, but interested in other options.

Boy, it has been a long while since I have done any synthesis. Let me get back to you, I wanna take a peak at the Beilstein manuals. They must be online somewhere.

Do you have access to a university or institutional library account? I would like some PDFs of some of my publications for my records.

I wish. Sounds like you need to friend a student at a university.

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Chemistry question:
Can acyl azides be prepared from carboxylic acids without activation of the carboxyl group (acyl chloride, anhydride, carbodiimide, active ester, etc.)? I’m preparing a precursor for Curtius rearrangement and hydrolysis to prepare the amine with one less C. (No other sensitive functional groups are present). Have you ever heard of cesium fluoride being used in this context? I know the best approach is to use DPPA, but interested in other options.

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Dope imma follow you, this will be interesting and welcome to steemit.

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Thank you! I contemplating next weeks post. Think I will have a very interesting one...........

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  ·  6 years ago (edited)

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