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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO5
Molecular Weight 373.4428
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N-BUTYRYL SCOPOLAMINE

SMILES

[H][C@@]12O[C@]1([H])[C@H]3C[C@H](C[C@@H]2N3C)OC(=O)[C@H](COC(=O)CCC)C4=CC=CC=C4

InChI

InChIKey=XYACSNDCQGUNGZ-OXAWTZHMSA-N
InChI=1S/C21H27NO5/c1-3-7-18(23)25-12-15(13-8-5-4-6-9-13)21(24)26-14-10-16-19-20(27-19)17(11-14)22(16)2/h4-6,8-9,14-17,19-20H,3,7,10-12H2,1-2H3/t14-,15-,16-,17+,19-,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H27NO5
Molecular Weight 373.4428
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Nociceptin/orphanin FQ and nocistatin on learning and memory impairment induced by scopolamine in mice.
1999 Jun
Scopolamine-induced convulsions in food given fasted mice: effects of clonidine and tizanidine.
1999 Jun
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
Glucose plus choline improve passive avoidance behaviour and increase hippocampal acetylcholine release in mice.
2001
Muscarinic cholinergic and glutamatergic reciprocal regulation of expression of hippocampal cholinergic neurostimulating peptide precursor protein gene in rat hippocampus.
2001
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.
2001 Apr 13
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
Comparative studies on the memory-enhancing actions of captopril and losartan in mice using inhibitory shock avoidance paradigm.
2001 Feb
Neural mechanisms of motion sickness.
2001 Feb
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
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry.
2001 Jan 5
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
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
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
Dose- and time-dependent scopolamine-induced recovery of an inhibitory avoidance response after its extinction in rats.
2001 Jun
Central and peripheral activity of cholinesterase inhibitors as revealed by yawning and fasciculation in rats.
2001 Mar
Memory impairment induced by cholinergic antagonists injected into the mushroom bodies of the honeybee.
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
Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats.
2001 Sep
Pharmacological modulation of behavioral and neuronal correlates of repetition priming.
2001 Sep 1
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 Sat Dec 16 01:27:06 UTC 2023
Edited
by admin
on Sat Dec 16 01:27:06 UTC 2023
Record UNII
HO322TV6PV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N-BUTYRYL SCOPOLAMINE
Common Name English
N-BUTYRYLSCOPOLAMINE
Common Name English
BENZENEACETIC ACID, .ALPHA.-((1-OXOBUTOXY)METHYL)-, 9-METHYL-3-OXA-9-AZATRICYCLO(3.3.1.0(SUP 2,4))NON-7-YL ESTER, (7(S)-(1.ALPHA.,2.BETA.,4.BETA.,5.ALPHA.,7.BETA.))-
Common Name English
Code System Code Type Description
FDA UNII
HO322TV6PV
Created by admin on Sat Dec 16 01:27:06 UTC 2023 , Edited by admin on Sat Dec 16 01:27:06 UTC 2023
PRIMARY
CAS
740757-65-7
Created by admin on Sat Dec 16 01:27:06 UTC 2023 , Edited by admin on Sat Dec 16 01:27:06 UTC 2023
PRIMARY
PUBCHEM
71587791
Created by admin on Sat Dec 16 01:27:06 UTC 2023 , Edited by admin on Sat Dec 16 01:27:06 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY