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.