SCOPOLAMINE
Structure, What is it?,History,
Biosynthesis, Metabolism and Excretion
STRUCTURE
L-Scopolamine
WHAT IS IT?
Tropane alkaloid and muscarinic antagonist.
Secondary metabolite
It comes from the Solanaceae family of plants,
like Jimnson weed or henbane.
HISTORY
One of the earliest alkaloids isolated from plants
by Albert Ladenburg in 1880, altough the jimson
weed was used in ancient and folk medicine.
In the 40s and 50s scopolamine was attempted to be
synthesized in a laboratory but other compounds were
obtained, such as diphenhydramine and pethidine.
HISTORY
In the 60s it began being used like an
anesthesic and analgesic mix with opioids
such as morphine and oxycodone.
Nowadays scopolamine is used in a little
dosage to treat postoperative nausea, motion
sickness, gastrointestinal spams... and it
works like a parasympathetic nervous system
antagonist.
In higher doses it is used as an antiparkinson
agent and as an anesthesic.
BIOSYNTHESIS
1.
2.
3.
Ornithine decarboxylase (Co-factor pyridoxal
5-phosphate)
Putrescine N-methyltransferase
Putrescine oxidase (Co-factor Cu(I))
Tropinone reductase 1
5. Cytochrome P450 (Cyp80F1)
6. 6--hydroxyhyoscyamine expoxidase (Cofactor L-acobate and Fe (II))
S. Spontaneous reaction
4.
SIMILAR COMPOUNDS
Atropine
METABOLISM AND RECEPTORS
Ways in which scopolamine can be
administrated.
METABOLISM AND RECEPTORS
When scopolamine is absorbed in the digestive
tract, it can go through the blood to different
muscarinic receptors.
A muscarinic receptor is a transmembrane
protein bonded with a G-protein.
MUSCARINIC RECEPTOR
MUSCARINIC RECEPTOR
METABOLISM, DEGRADATION
AND EXCRETION
The maximum effect is seen after 1-2 hours.
Scopolamine is degraded in the liver through
enzymatic hydrolysis.
Its excreted by the kindey.
TRIVIA
Scopolamine is also called Burundanga.
BIBLIOGRAPHY
Putcha, L.; Cintrn, N. M.; Tsui, J.; Vanderploeg, J. M.; Kramer, W. G.
(1989). "Pharmacokinetics and Oral Bioavailability of Scopolamine in
Normal Subjects".
Renner UD,Oertel R,Kirch W. Pharmacokinetics and pharmacodynamics
in clinical use of scopolamine.
Grzegorz Grynkiewicz, Maria Gadzikowska. Tropane alkaloids as
medicinally useful natural products and their synthetic derivatives as new
drugs.
Flores Soto ME, Segura Torres JE. Estructura y funcin de los receptores
acetilcolina de tipo muscarnico y nicotnico.
Rong Li, Darwin W. Reed, Enwu Liu, Jacek Nowak, Lawrence E. Pelcher,1
Jonathan E. Page and Patrick S. Covello. Functional Genomic Analysis of
Alkaloid Biosynthesis in Hyoscyamus niger Reveals a Cytochrome P450
Involved in Littorine Rearrangement.
