U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4.BrH.3H2O
Molecular Weight 438.311
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SCOPOLAMINE HYDROBROMIDE

SMILES

O.O.O.Br.[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2N3C)OC(=O)[C@H](CO)C4=CC=CC=C4

InChI

InChIKey=LACQPOBCQQPVIT-SEYKEWMNSA-N
InChI=1S/C17H21NO4.BrH.3H2O/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;1H;3*1H2/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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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).

Originator

Sources: A. Ladenburg, Ann. 206, 274 (1881); E. Schmidt, Arch. Pharm. 230, 207 (1892).
Curator's Comment: Scopolamine is an anticholinergic, tropane alkaloid isolated from Datura metel L., Scopola carniolica Jacq. and other Solanaceae. Constituent of impure duboisine from Duboisia myoporoides R. Br., pure duboisine is l-hyoscyamine, q.v. reference retrieved from http://www.drugfuture.com/chemdata/scopolamine.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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

3.15446395E11
Preventing
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

3.15446395E11
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2.1 ng × h/mL
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
369 ng × min/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.5 h
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
68.7 min
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
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

Doses

DosePopulationAdverse events​
0.4 mg single, intranasal
Highest studied dose
Dose: 0.4 mg
Route: intranasal
Route: single
Dose: 0.4 mg
Sources:
healthy, 21 - 47 years
n = 12
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
Population Size: 12
Sources:
Other AEs: Dizziness, Lightheadedness...
Other AEs:
Dizziness (3 patients)
Lightheadedness (3 patients)
Nasal burning (1 patient)
Sources:
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:
healthy, 21.4 years
n = 35
Health Status: healthy
Age Group: 21.4 years
Sex: M
Population Size: 35
Sources:
Other AEs: Blurred vision, Dizziness...
Other AEs:
Blurred vision
Dizziness
Sources:
6 ug/kg single, intravenous
Dose: 6 ug/kg
Route: intravenous
Route: single
Dose: 6 ug/kg
Sources:
healthy, 22.8 years
n = 9
Health Status: healthy
Age Group: 22.8 years
Sex: M
Population Size: 9
Sources:
1.2 mg single, oral
Highest studied dose
Dose: 1.2 mg
Route: oral
Route: single
Dose: 1.2 mg
Sources:
healthy, 24 years (range: 19-38 years)
n = 12
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
Population Size: 12
Sources:
Other AEs: Dizziness, Dry mouth...
Other AEs:
Dizziness (4 patients)
Dry mouth (3 patients)
Blurred vision (4 patients)
Sources:
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:
unhealthy, 83 years
n = 1
Health Status: unhealthy
Age Group: 83 years
Sex: F
Population Size: 1
Sources:
Other AEs: Consciousness abnormal, Hyperthermia...
Other AEs:
Consciousness abnormal (1 patient)
Hyperthermia (1 patient)
Sources:
0.5 mg single, intravenous
Dose: 0.5 mg
Route: intravenous
Route: single
Dose: 0.5 mg
Sources:
healthy, adult
n = 6
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 6
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 21 - 47 years
n = 12
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
Population Size: 12
Sources:
Dizziness 3 patients
0.4 mg single, intranasal
Highest studied dose
Dose: 0.4 mg
Route: intranasal
Route: single
Dose: 0.4 mg
Sources:
healthy, 21 - 47 years
n = 12
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
Population Size: 12
Sources:
Lightheadedness 3 patients
0.4 mg single, intranasal
Highest studied dose
Dose: 0.4 mg
Route: intranasal
Route: single
Dose: 0.4 mg
Sources:
healthy, 21 - 47 years
n = 12
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
Population Size: 12
Sources:
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:
healthy, 21.4 years
n = 35
Health Status: healthy
Age Group: 21.4 years
Sex: M
Population Size: 35
Sources:
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:
healthy, 21.4 years
n = 35
Health Status: healthy
Age Group: 21.4 years
Sex: M
Population Size: 35
Sources:
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:
healthy, 24 years (range: 19-38 years)
n = 12
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
Population Size: 12
Sources:
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:
healthy, 24 years (range: 19-38 years)
n = 12
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
Population Size: 12
Sources:
Dizziness 4 patients
1.2 mg single, oral
Highest studied dose
Dose: 1.2 mg
Route: oral
Route: single
Dose: 1.2 mg
Sources:
healthy, 24 years (range: 19-38 years)
n = 12
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
Population Size: 12
Sources:
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:
unhealthy, 83 years
n = 1
Health Status: unhealthy
Age Group: 83 years
Sex: F
Population Size: 1
Sources:
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:
unhealthy, 83 years
n = 1
Health Status: unhealthy
Age Group: 83 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
yes [IC50 119.2 uM]
yes [IC50 217.9 uM]
yes [IC50 540.8 uM]
yes [IC50 6.7 uM]
yes [IC50 699.9 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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)
PubMed

PubMed

TitleDatePubMed
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs.
1976 Aug
Behavioral studies of the effects of moderate oligemic hypoxia caused by bilateral clamping of carotid arteries in mice. Impairment of spatial working memory.
1998 Jul-Oct
Korean red ginseng saponins with low ratios of protopanaxadiol and protopanaxatriol saponin improve scopolamine-induced learning disability and spatial working memory in mice.
1999 Aug
Nociceptin/orphanin FQ and nocistatin on learning and memory impairment induced by scopolamine in mice.
1999 Jun
American ginseng extract reduces scopolamine-induced amnesia in a spatial learning task.
1999 Nov
S 15535, a benzodioxopiperazine acting as presynaptic agonist and postsynaptic 5-HT1A receptor antagonist, prevents the impairment of spatial learning caused by intrahippocampal scopolamine.
1999 Nov
Effects of histamine H3 receptor agonists and antagonists on cognitive performance and scopolamine-induced amnesia.
1999 Oct
Intra-medial prefrontal cortex injections of scopolamine increase instrumental responses for cocaine: an intravenous self-administration study in rats.
2000 Jan 15
Probing peripheral and central cholinergic system responses.
2000 Sep
Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats.
2001 Apr
Interactions between allosteric modulators and 4-DAMP and other antagonists at muscarinic receptors: potential significance of the distance between the N and carboxyl C atoms in the molecules of antagonists.
2001 Apr
Male-female differences in rat hypothalamic-pituitary-adrenal axis responses to nicotine stimulation.
2001 Apr
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.
2001 Apr 13
Neostriatal muscarinic receptor subtypes involved in the generation of tremulous jaw movements in rodents implications for cholinergic involvement in parkinsonism.
2001 Apr 27
Antimuscarinic treatment for lung diseases from research to clinical practice.
2001 Apr 27
Ultrasonic vocalizations as an index of social memory in female mice.
2001 Aug
Long-lasting cholinergic modulation underlies rule learning in rats.
2001 Feb 15
Sexual diergism in rat hypothalamic-pituitary-adrenal axis responses to cholinergic stimulation and antagonism.
2001 Jan 1
Scopolamine fails to diminish chronic haloperidol-induced purposeless chewing in rats.
2001 Jan 1
Effects of the 5-HT(6) receptor antagonist Ro 04-6790 on learning consolidation.
2001 Jan 8
The effects of scopolamine on the spatial organization of cortical potentials in the rat brain.
2001 Jan-Feb
Occurrence of cadaverine in hairy roots of Brugmansia candida.
2001 Jul
Anti-ischemic and cognition-enhancing properties of NNC-711, a gamma-aminobutyric acid reuptake inhibitor.
2001 Jul 13
Drug-induced variations in the probability of occurrence of multiple corrective saccades.
2001 Jun
Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum.
2001 Jun
Dose- and time-dependent scopolamine-induced recovery of an inhibitory avoidance response after its extinction in rats.
2001 Jun
Could the 5-HT1B receptor inverse agonism affect learning consolidation?
2001 Mar
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Evidence for involvement of central 5-HT(4) receptors in cholinergic function associated with cognitive processes: behavioral, electrophysiological, and neurochemical studies.
2001 Mar
Memory impairment induced by cholinergic antagonists injected into the mushroom bodies of the honeybee.
2001 May
The role of muscarinic cholinoceptors in the retrieval of an operant food-related conditioned reflex in cats.
2001 May-Jun
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
2001 Sep
Patents

Sample Use Guides

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
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 Thu Jul 06 00:40:58 UTC 2023
Edited
by admin
on Thu Jul 06 00:40:58 UTC 2023
Record UNII
451IFR0GXB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SCOPOLAMINE HYDROBROMIDE
USP   USP-RS   VANDF  
Common Name English
Hyoscine hydrobromide trihydrate [WHO-DD]
Common Name English
HYOSCINE HYDROBROMIDE [VANDF]
Common Name English
SCOPOLAMINUM HYDROBROMIDUM [HPUS]
Common Name English
HYOSCINE HYDROBROMIDE
EP   MART.   VANDF  
Common Name English
SCOPOLAMINE HBR
Common Name English
HYOSCINE HYDROBROMIDE TRIHYDRATE
WHO-DD  
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, HYDROBROMIDE, HYDRATE (1:1:3), (.ALPHA.S)-
Systematic Name English
6.BETA.,7.BETA.-EPOXY-1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (-)-TROPATE (ESTER) HYDROBROMIDE TRIHYDRATE
Common Name English
SCOPOLAMINE HYDROBROMIDE, TRIHYDRATE
Common Name English
SCOPOLAMINE HYDROBROMIDE TRIHYDRATE [MI]
Common Name English
SCOPOLAMINE HYDROBROMIDE HYDRATE
JAN  
Common Name English
HYOSCINE HBR
Common Name English
SCOPOLAMINE HYDROBROMIDE [VANDF]
Common Name English
SCOPOLAMINE HBR, TRIHYDRATE
Common Name English
SCOPOLAMINE HYDROBROMIDE [USP-RS]
Common Name English
SCOPOLAMINUM HYDROBROMIDUM
HPUS  
Common Name English
NSC-757314
Code English
SCOPOLAMINE HYDROBROMIDE HYDRATE [JAN]
Common Name English
(-)-SCOPOLAMINE HYDROBROMIDE TRIHYDRATE
Common Name English
SCOPOLAMINE HYDROBROMIDE TRIHYDRATE
MI  
Common Name English
ISOPTO HYOSCINE
Brand Name English
SCOPOLAMINE HYDROBROMIDE [USP MONOGRAPH]
Common Name English
TRANSDERM-SCOP
Brand Name English
HYOSCINE HYDROBROMIDE [EP MONOGRAPH]
Common Name English
HYOSCINE HYDROBROMIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
NCI_THESAURUS C29706
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
EPA PESTICIDE CODE 600094
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 8.4
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
Code System Code Type Description
MERCK INDEX
M9813
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY Merck Index
EVMPD
SUB14155MIG
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
NCI_THESAURUS
C29446
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
FDA UNII
451IFR0GXB
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
ChEMBL
CHEMBL1187846
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
CHEBI
16794
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
EVMPD
SUB77813
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
CHEBI
61272
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
RS_ITEM_NUM
1610001
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
NSC
757314
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
CHEBI
61271
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
EPA CompTox
DTXSID0021258
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
RXCUI
9603
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY RxNorm
DAILYMED
451IFR0GXB
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
CAS
6533-68-2
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
MESH
D012601
Created by admin on Thu Jul 06 00:40:58 UTC 2023 , Edited by admin on Thu Jul 06 00:40:58 UTC 2023
PRIMARY
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