SCOPOLAMINE

First marketed in 1899

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H21NO4
Molecular Weight	303.3529
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2C[C@@H](C[C@@H]1[C@H]3O[C@@H]23)OC(=O)[C@H](CO)C4=CC=CC=C4

InChI

InChIKey=STECJAGHUSJQJN-FWXGHANASA-N

InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C17H21NO4
Molecular Weight	303.3529
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16175141 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017874s038lbl.pdf

The alkaloid L-(-)-scopolamine [L-(-)-hyoscine], a belladonna alkaloid, competitively inhibits muscarinic receptors for acetylcholine and acts as a nonselective muscarinic antagonist, producing both peripheral antimuscarinic properties and central sedative, antiemetic, and amnestic effects. Scopolamine acts: i) as a competitive inhibitor at postganglionic muscarinic receptor sites of the parasympathetic nervous system, and ii) on smooth muscles that respond to acetylcholine but lack cholinergic innervation. It has been suggested that scopolamine acts in the central nervous system (CNS) by blocking cholinergic transmission from the vestibular nuclei to higher centers in the CNS and from the reticular formation to the vomiting center. Scopolamine can inhibit the secretion of saliva and sweat, decrease gastrointestinal secretions and motility, cause drowsiness, dilate the pupils, increase heart rate, and depress motor function. Scopolamine is used for premedication in anesthesia and for the prevention of nausea and vomiting (post operative and associated with motion sickness).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27108935	Antagonist 2849		2.09 µM [IC50]
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2094109 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1727135 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017874s038lbl.pdf	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Motion sickness 43 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017874s038lbl.pdf	Preventing	Approved 8583	TRANSDERM SCOP Approved Use Transderm Scōp is an anticholinergic agent indicated in adults for the prevention of nausea and vomiting associated with: Motion Sickness and Post Operative Nausea and Vomiting (PONV) Launch Date 1979
Postoperative nausea and vomiting 31 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/017874s038lbl.pdf	Preventing	Approved 8583	TRANSDERM SCOP Approved Use Transderm Scōp is an anticholinergic agent indicated in adults for the prevention of nausea and vomiting associated with: Motion Sickness and Post Operative Nausea and Vomiting (PONV) Launch Date 1979
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17015814 https://www.ncbi.nlm.nih.gov/pubmed/23334071	Primary	Phase IV 63	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/16175141/	0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SCOPOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
369 ng × min/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/16175141/	0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SCOPOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.1 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf	1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered:		SCOPOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
68.7 min REVIEW https://pubmed.ncbi.nlm.nih.gov/16175141/	0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SCOPOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf	1 mg single, topical dose: 1 mg route of administration: Topical experiment type: SINGLE co-administered:		SCOPOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
70% REVIEW https://pubmed.ncbi.nlm.nih.gov/16175141/	0.5 mg single, intravenous dose: 0.5 mg route of administration: Intravenous experiment type: SINGLE co-administered:		SCOPOLAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/	healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/	Other AEs: Dizziness, Lightheadedness... Other AEs: Dizziness (3 patients) Lightheadedness (3 patients) Nasal burning (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/
0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6873137	healthy, 21.4 years Health Status: healthy Age Group: 21.4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6873137	Other AEs: Blurred vision, Dizziness... Other AEs: Blurred vision Dizziness Sources: https://pubmed.ncbi.nlm.nih.gov/6873137
6 ug/kg single, intravenous Dose: 6 ug/kg Route: intravenous Route: single Dose: 6 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/6873137	healthy, 22.8 years Health Status: healthy Age Group: 22.8 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6873137	Sources: https://pubmed.ncbi.nlm.nih.gov/6873137
1.2 mg single, oral Highest studied dose Dose: 1.2 mg Route: oral Route: single Dose: 1.2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3088662	healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3088662	Other AEs: Dizziness, Dry mouth... Other AEs: Dizziness (4 patients) Dry mouth (3 patients) Blurred vision (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/3088662
10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25395072	unhealthy, 83 years Health Status: unhealthy Age Group: 83 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/25395072	Other AEs: Consciousness abnormal, Hyperthermia... Other AEs: Consciousness abnormal (1 patient) Hyperthermia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/25395072
0.5 mg single, intravenous Dose: 0.5 mg Route: intravenous Route: single Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15792397	healthy, adult Health Status: healthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/15792397	Sources: https://pubmed.ncbi.nlm.nih.gov/15792397

AEs

AE	Significance	Dose	Population
Nasal burning	1 patient	0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/	healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/
Dizziness	3 patients	0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/	healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/
Lightheadedness	3 patients	0.4 mg single, intranasal Highest studied dose Dose: 0.4 mg Route: intranasal Route: single Dose: 0.4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/	healthy, 21 - 47 years Health Status: healthy Age Group: 21 - 47 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/25187210/
Blurred vision		0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6873137	healthy, 21.4 years Health Status: healthy Age Group: 21.4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6873137
Dizziness		0.9 mg 2 times / day multiple, oral Highest studied dose Dose: 0.9 mg, 2 times / day Route: oral Route: multiple Dose: 0.9 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6873137	healthy, 21.4 years Health Status: healthy Age Group: 21.4 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6873137
Dry mouth	3 patients	1.2 mg single, oral Highest studied dose Dose: 1.2 mg Route: oral Route: single Dose: 1.2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3088662	healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3088662
Blurred vision	4 patients	1.2 mg single, oral Highest studied dose Dose: 1.2 mg Route: oral Route: single Dose: 1.2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3088662	healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3088662
Dizziness	4 patients	1.2 mg single, oral Highest studied dose Dose: 1.2 mg Route: oral Route: single Dose: 1.2 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3088662	healthy, 24 years (range: 19-38 years) Health Status: healthy Age Group: 24 years (range: 19-38 years) Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/3088662
Consciousness abnormal	1 patient	10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25395072	unhealthy, 83 years Health Status: unhealthy Age Group: 83 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/25395072
Hyperthermia	1 patient	10 mg 3 times / day multiple, oral Overdose Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25395072	unhealthy, 83 years Health Status: unhealthy Age Group: 83 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/25395072

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C8 1057 CYP2C19 2057 OCT1 620 OCT2 779 OCT3 159 MATE1 415 MATE2 267	CYP3A 220	CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017874s043s044lbl.pdf#page=5 Page: 5.0	no
MATE1 416	inhibitor 4027 Sources: https://www.degruyter.com/document/doi/10.1515/hsz-2016-0236/html Page: 21.0	yes [IC50 119.2 uM]
OCT3 161	inhibitor 4027 Sources: https://www.degruyter.com/document/doi/10.1515/hsz-2016-0236/html Page: 21.0	yes [IC50 217.9 uM]
OCT2 782	inhibitor 4027 Sources: https://www.degruyter.com/document/doi/10.1515/hsz-2016-0236/html Page: 21.0	yes [IC50 540.8 uM]
OCT1 656	inhibitor 4027 Sources: https://www.degruyter.com/document/doi/10.1515/hsz-2016-0236/html Page: 21.0	yes [IC50 6.7 uM]
MATE2 267	inhibitor 4027 Sources: https://www.degruyter.com/document/doi/10.1515/hsz-2016-0236/html Page: 21.0	yes [IC50 699.9 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A 220	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16175141/	yes		yes (co-administration study) Comment: The AUC0–24h values of scopolamine were higher during the grapefruit juice period. They reached approximately 142% of the values associated with the control group (water period; P . 0.005) Sources: https://pubmed.ncbi.nlm.nih.gov/16175141/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16794	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16794
MolPort	MolPort-005-938-576	https://www.molport.com/shop/molecule-link/MolPort-005-938-576
ZINC	ZINC000100037020	http://zinc15.docking.org/substances/ZINC000100037020

PubMed

Title	Date	PubMed
Scopolamine-induced convulsions in food given fasted mice: effects of clonidine and tizanidine.	1999 Jun	10372568
A novel nitrate ester reverses the cognitive impairment caused by scopolamine in the Morris water maze.	2000 Nov 27	11117508
Probing peripheral and central cholinergic system responses.	2000 Sep	11022397
Scopolamine does not restore normal conditioned avoidance performance in raclopride-treated rats.	2001	11475009
Intrastriatal GABA(A) receptor blockade does not alter dopamine D(1)/D(2) receptor interactions in the intact rat striatum.	2001	11166124
Muscarinic cholinergic and glutamatergic reciprocal regulation of expression of hippocampal cholinergic neurostimulating peptide precursor protein gene in rat hippocampus.	2001	11166120
Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats.	2001 Apr	11526961
Infralimbic muscarinic M1 receptors modulate anxiety-like behaviour and spontaneous working memory in mice.	2001 Apr	11374337
Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.	2001 Apr	11345697
Auditory sensory memory and the cholinergic system: implications for Alzheimer's disease.	2001 Aug	11467911
Comparative studies on the memory-enhancing actions of captopril and losartan in mice using inhibitory shock avoidance paradigm.	2001 Feb	11346312
Evaluation of novel PET ligands (+)N-[11C]methyl-3-piperidyl benzilate ([11C](+)3-MPB) and its stereoisomer [11C](-)3-MPB for muscarinic cholinergic receptors in the conscious monkey brain: a PET study in comparison with.	2001 Feb	11180506
Inhaled anticholinergic therapy: applied pharmacology and interesting developments.	2001 Jan	11527013
Designing of an orally active complement C3a agonist peptide with anti-analgesic and anti-amnesic activity.	2001 Jan	11179594
Scopolamine bioavailability in combined oral and transdermal delivery.	2001 Jan	11123371
Occurrence of cadaverine in hairy roots of Brugmansia candida.	2001 Jul	11397445
Anti-ischemic and cognition-enhancing properties of NNC-711, a gamma-aminobutyric acid reuptake inhibitor.	2001 Jul 13	11470258
Evidence for involvement of central 5-HT(4) receptors in cholinergic function associated with cognitive processes: behavioral, electrophysiological, and neurochemical studies.	2001 Mar	11181892
Long-term potentiation in hippocampus of rats is enhanced by endogenous acetylcholine in a way that is independent of N-methyl-D-aspartate receptors.	2001 Mar 16	11226632
Subchronic administration of various pretreatments of nerve agent poisoning. II. Compared efficacy against soman toxicity.	2001 May	11360433
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms.	2001 May	11072041

Patents

Sample Use Guides

In Vivo Use Guide

Transderm Scōp (scopolamine) transdermal system patch. Each Transderm Scōp patch is formulated to deliver in-vivo approximately 1 mg of scopolamine over 3 days. Initiation of Therapy Motion Sickness To prevent the nausea and vomiting associated with motion sickness, one Transderm Scōp patch (formulated to deliver approximately 1 mg of scopolamine over 3 days) should be applied to the hairless area behind one ear at least 4 hours before the antiemetic effect is required. Post Operative Nausea and Vomiting To prevent post operative nausea and vomiting, one Transderm Scōp patch should be applied the evening before scheduled surgery, except for caesarian section. For caesarian section surgery, to minimize exposure of the newborn baby to the drug, apply the patch one hour prior to caesarian section. Continuation of Therapy Should the patch become displaced, it should be discarded, and a fresh one placed on the hairless area behind the other ear. Motion Sickness If therapy is required for longer than 3 days, the first patch should be removed and a fresh one placed on the hairless area behind the other ear. Post Operative Nausea and Vomiting For perioperative use, the patch should be kept in place for 24 hours following surgery at which time it should be removed and discarded.

Route of Administration: Transdermal

In Vitro Use Guide

Rosmarinic acid treatment increases the expression of BDNF and GluR-2 proteins and prevents cell death of scopolamine-exposed (300 μM) organotypic hippocampal slice cultures.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:57 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:57 GMT 2025`
Record UNII	DL48G20X8X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SCOPOLAMINE

Common Name

English

HYOSCINE

Preferred Name

English

HYOSCINE [EP MONOGRAPH]

Common Name

English

SCOPOLAMINE [MI]

Common Name

English

SCOPOLAMINE [USP IMPURITY]

Common Name

English

SCOPOLAMINE [ORANGE BOOK]

Common Name

English

HYOSCINE [EP IMPURITY]

Common Name

English

SCOPOLAMINE [VANDF]

Common Name

English

BENZENEACETIC ACID, .ALPHA.(HYDROXYMETHYL)-,(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.)-9-METHYL-3-OXA-9-AZATRICYCLO(3.3.1.02,4)NON-7-YL ESTER, (.ALPHA.S)-

Common Name

English

6.BETA.,7.BETA.-EPOXY-1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (-)-TROPATE (ESTER)

Common Name

English

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 9-METHYL-3-OXA-9-AZATRICYCLO(3.3.1.02,4)NON-7-YL ESTER, (7(S)-(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.))-

Common Name

English

(1R,2R,4S,5S,7S)-9-METHYL-3-OXA-9-AZATRICYCLO(3.3.1.02,4)NON-7-YL (2S)-3-HYDROXY-2-PHENYLPROPANOATE

Common Name

English

HYOSCINE [MART.]

Common Name

English

ATROPINE SULFATE IMPURITY F [EP IMPURITY]

Common Name

English

SCOPOLAMINE [HSDB]

Common Name

English

Hyoscine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A04AD51