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

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21NO4.BrH
Molecular Weight 384.265
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SCOPOLAMINE HYDROBROMIDE ANHYDROUS

SMILES

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=WTGQALLALWYDJH-MOUKNHLCSA-N
InChI=1S/C17H21NO4.BrH/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/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 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

1979
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

1979
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
Scopolamine does not restore normal conditioned avoidance performance in raclopride-treated rats.
2001
Nucleus accumbens muscarinic receptors in the control of behavioral depression: antidepressant-like effects of local M1 antagonist in the Porsolt swim test.
2001
Interactions between cholinergic and GABAergic neurotransmitters in and around the locus coeruleus for the induction and maintenance of rapid eye movement sleep in rats.
2001
Dopaminergic lateralisation in the forebrain: relations to behavioural asymmetries and anxiety in male Wistar rats.
2001
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
Infralimbic muscarinic M1 receptors modulate anxiety-like behaviour and spontaneous working memory in mice.
2001 Apr
Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.
2001 Apr
Compensatory mechanisms enhance hippocampal acetylcholine release in transgenic mice expressing human acetylcholinesterase.
2001 Apr
Tiotropium bromide.
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
M5 muscarinic receptors are needed for slow activation of dopamine neurons and for rewarding brain stimulation.
2001 Apr 27
Pentyl-4-yn-valproic acid enhances both spatial and avoidance learning, and attenuates age-related NCAM-mediated neuroplastic decline within the rat medial temporal lobe.
2001 Aug
Ultrasonic vocalizations as an index of social memory in female mice.
2001 Aug
Auditory sensory memory and the cholinergic system: implications for Alzheimer's disease.
2001 Aug
Cholinergic synaptic potentials in the supragranular layers of auditory cortex.
2001 Aug
Comparative studies on the memory-enhancing actions of captopril and losartan in mice using inhibitory shock avoidance paradigm.
2001 Feb
Differences in parasympathetic vasodilator and salivary responses in the cat submandibular gland between lingual and chorda-lingual nerve stimulation.
2001 Feb
Neural mechanisms of motion sickness.
2001 Feb
Inhaled anticholinergic therapy: applied pharmacology and interesting developments.
2001 Jan
Effects of Hypericum perforatum (St. John's wort) on passive avoidance in the rat: evaluation of potential neurochemical mechanisms underlying its antidepressant activity.
2001 Jul
Differential effects of trihexyphenidyl on place preference conditioning and locomotor stimulant activity of cocaine and methamphetamine.
2001 Jul
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
Effects of vasopressin on histamine H(1) receptor antagonist-induced spatial memory deficits in rats.
2001 Jul 6
Interaction between the cholinergic system and CRH in the modulation of spatial discrimination learning in mice.
2001 Jul 6
Hairy roots of Brugmansia candida that grow without agitation: biotechnological implications.
2001 Jul-Aug
Drug-induced variations in the probability of occurrence of multiple corrective saccades.
2001 Jun
The alpha 2 adrenoceptor antagonists RX 821002 and yohimbine delay-dependently impair choice accuracy in a delayed non-matching-to-position task in rats.
2001 Jun
Y-27632, an inhibitor of Rho-kinase, antagonizes noradrenergic contractions in the rabbit and human penile corpus cavernosum.
2001 Jun
N-tert-butyl-alpha-phenylnitrone, a free radical scavenger with anticholinesterase activity does not improve the cognitive performance of scopolamine-challenged rats.
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
The role of the cholinergic system of the sensorimotor cortex of the rat brain in controlling different types of movement.
2001 Mar-Apr
Memory impairment induced by cholinergic antagonists injected into the mushroom bodies of the honeybee.
2001 May
Subchronic administration of various pretreatments of nerve agent poisoning. II. Compared efficacy against soman toxicity.
2001 May
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.
2001 May
Intrahippocampal scopolamine impairs both acquisition and consolidation of contextual fear conditioning.
2001 May
Scopolamine nasal spray in motion sickness: a randomised, controlled, and crossover study for the comparison of two scopolamine nasal sprays with oral dimenhydrinate and placebo.
2001 May
Excitatory nicotinic and desensitizing muscarinic (M2) effects on C-nociceptors in isolated rat skin.
2001 May 1
The role of muscarinic cholinoceptors in the retrieval of an operant food-related conditioned reflex in cats.
2001 May-Jun
The acetylcholine release enhancer linopirdine induces Fos in neocortex of aged rats.
2001 May-Jun
Release of non-neuronal acetylcholine from the human placenta: difference to neuronal acetylcholine.
2001 Sep
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
2001 Sep
Substance P and its transglutaminase-synthesized spermine derivative elicit yawning behavior via nitric oxide in rats.
2001 Sep
Pharmacological modulation of behavioral and neuronal correlates of repetition priming.
2001 Sep 1
Simultaneous modulation of retrieval by dopaminergic D(1), beta-noradrenergic, serotonergic-1A and cholinergic muscarinic receptors in cortical structures of the rat.
2001 Sep 28
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 Fri Dec 15 19:48:09 GMT 2023
Edited
by admin
on Fri Dec 15 19:48:09 GMT 2023
Record UNII
R3K67DRL3J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SCOPOLAMINE HYDROBROMIDE ANHYDROUS
Common Name English
NSC-61806
Code English
SCOPOLAMINE HYDROBROMIDE [MI]
Common Name English
6.BETA.,7.BETA.-EPOXY-1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (-)-TROPATE (ESTER) HYDROBROMIDE
Common Name English
Hyoscine hydrobromide [WHO-DD]
Common Name English
Code System Code Type Description
NSC
61806
Created by admin on Fri Dec 15 19:48:09 GMT 2023 , Edited by admin on Fri Dec 15 19:48:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-050-6
Created by admin on Fri Dec 15 19:48:09 GMT 2023 , Edited by admin on Fri Dec 15 19:48:09 GMT 2023
PRIMARY
FDA UNII
R3K67DRL3J
Created by admin on Fri Dec 15 19:48:09 GMT 2023 , Edited by admin on Fri Dec 15 19:48:09 GMT 2023
PRIMARY
CAS
114-49-8
Created by admin on Fri Dec 15 19:48:09 GMT 2023 , Edited by admin on Fri Dec 15 19:48:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID0032029
Created by admin on Fri Dec 15 19:48:09 GMT 2023 , Edited by admin on Fri Dec 15 19:48:09 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY