- #1
Mr_Bojingles
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Is it possible to synthesize adrenaline in the lab?
Is it possible to synthesize adrenaline in the lab?
- Thread starter Mr_Bojingles
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SUMMARY
It is indeed possible to synthesize adrenaline in the lab using specific chemical processes. The synthesis can begin with 2-Chloro-1-(3,4-dihydroxyphenyl)ethanone, which is available from suppliers like Alpha Aesar for approximately $283 per 500 g. The synthesis involves a substitution reaction with methyl amine and a stereoselective reduction using 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole and Borane Dimethyl sulfide complex in THF, yielding over 75%. Historical context indicates that adrenaline was first synthesized by Friedrich Stolz in 1904.
PREREQUISITES- Knowledge of organic chemistry synthesis techniques
- Familiarity with substitution reactions and stereoselective reductions
- Understanding of chemical reagents such as methyl amine and Borane Dimethyl sulfide
- Experience with laboratory equipment and safety protocols
- Research the properties and applications of 2-Chloro-1-(3,4-dihydroxyphenyl)ethanone
- Study the mechanisms of substitution reactions in organic chemistry
- Learn about stereoselective reduction techniques and their importance in synthesis
- Investigate the historical synthesis of adrenaline and its implications in pharmacology
Chemists, pharmacologists, and students of organic chemistry seeking to understand the synthesis of biologically active compounds like adrenaline.
- #2
gravenewworld
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Mr_Bojingles said:
Yes it shouldn't be taht hard.
- #3
JGM_14
- 157
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our body does it all the time 
- #4
gravenewworld
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I did a search for possible starting materials and looked at the cost vs. how many steps for a possible synthesis and you could do it this way:
Buy 2-Chloro-1-(3,4-dihydroxyphenyl)ethanone, 97% (500 g, $283 Alpha Aesar)
Do a substitution of the chlorine with methyl amine (use a large excess of methyl amine).
Reduce the carbonyl stereoselectively using 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole, tetrahydro-1-methyl-3,3-diphenyl-, (S)- with Borane Dimethyl sulfide complex in THF.
I've done the reduction before, it works pretty well (>75% yield)
That should give you adrenaline.
Buy 2-Chloro-1-(3,4-dihydroxyphenyl)ethanone, 97% (500 g, $283 Alpha Aesar)
Do a substitution of the chlorine with methyl amine (use a large excess of methyl amine).
Reduce the carbonyl stereoselectively using 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole, tetrahydro-1-methyl-3,3-diphenyl-, (S)- with Borane Dimethyl sulfide complex in THF.
I've done the reduction before, it works pretty well (>75% yield)
That should give you adrenaline.
- #5
quetzalcoatl9
- 535
- 1
JGM_14 said:our body does it all the time
that doesn't means it's easy, in fact it's generally the opposite. enzymes regularly do chemistry that we can't dream of doing in the lab.
- #6
JGM_14
- 157
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quetzalcoatl9 said:
Point taken.
- #7
brewnog
Science Advisor
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Apparently, it was first synthesised in the lab in 1904 by Freidrich Stolz...
- #8
Remnant
- 19
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Hint: Meth is 1 atom away from adrenaline..
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