Background
I recently experiment in "chewing" the muscle relaxant Tolperisone for random curiosity reason (just indicated dose; 50mg)
Surprisingly it has pungent and peppery taste! which lingers in my mount for a while even when drinking a glass of water afterward.
In the next day I try another brand of tolperisone and it has the same taste, but it is less pungent despite being the same dosage tablet.
Question!
Where is this pungency taste originated from?
- Is it from the Tolperisone itself? It has vaguely-somewhat-similar structure to piperine, which is the cheif reason for black pepper taste.
Several compounds with similar structure do have this similar characteristic taste,
for example. Chavicine (cistrans isomer of piperine), "piperane" (piperine hydrogenated to remove double bonds), Ilepcimide (piperine with shortened chain, one double bond removed)
or even piperine with the methylenedioxy group removed from benzene ring, or piperine with 3,4-dimethyl- instead of methylenedioxy
- Is it from Piperidine which is the degradation product of Tolperisone during manufacturing/storage? I've tasted very dilute solution of piperidine in ethanol years ago;
it has fishy smell (which is abit more "heavy/greasy"-taste than trimethylamine), but still have its pungency.
Edit: Second-surprising experiment: Eperisone does NOT have this taste. It differs from tolperisone that methyl is changed to ethyl group.
Edit2: Added wiki link so you can compare some structure:
https://en.wikipedia.org/wiki/Tolperisone
https://en.wikipedia.org/wiki/Eperisone
https://en.wikipedia.org/wiki/Piperine
https://en.wikipedia.org/wiki/Chavicine
https://en.wikipedia.org/wiki/Ilepcimide
https://en.wikipedia.org/wiki/Piperidine
Degradation of tolperisone to release piperidine: https://www.hindawi.com/journals/jac/2013/352984/
I recently experiment in "chewing" the muscle relaxant Tolperisone for random curiosity reason (just indicated dose; 50mg)
Surprisingly it has pungent and peppery taste! which lingers in my mount for a while even when drinking a glass of water afterward.
In the next day I try another brand of tolperisone and it has the same taste, but it is less pungent despite being the same dosage tablet.
Question!
Where is this pungency taste originated from?
- Is it from the Tolperisone itself? It has vaguely-somewhat-similar structure to piperine, which is the cheif reason for black pepper taste.
Several compounds with similar structure do have this similar characteristic taste,
for example. Chavicine (cistrans isomer of piperine), "piperane" (piperine hydrogenated to remove double bonds), Ilepcimide (piperine with shortened chain, one double bond removed)
or even piperine with the methylenedioxy group removed from benzene ring, or piperine with 3,4-dimethyl- instead of methylenedioxy
- Is it from Piperidine which is the degradation product of Tolperisone during manufacturing/storage? I've tasted very dilute solution of piperidine in ethanol years ago;
it has fishy smell (which is abit more "heavy/greasy"-taste than trimethylamine), but still have its pungency.
Edit: Second-surprising experiment: Eperisone does NOT have this taste. It differs from tolperisone that methyl is changed to ethyl group.
Edit2: Added wiki link so you can compare some structure:
https://en.wikipedia.org/wiki/Tolperisone
https://en.wikipedia.org/wiki/Eperisone
https://en.wikipedia.org/wiki/Piperine
https://en.wikipedia.org/wiki/Chavicine
https://en.wikipedia.org/wiki/Ilepcimide
https://en.wikipedia.org/wiki/Piperidine
Degradation of tolperisone to release piperidine: https://www.hindawi.com/journals/jac/2013/352984/