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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

CCCC(=O)OC[C@@H](C(=O)O[C@H]1C[C@H]2[C@@H]3O[C@@H]3[C@@H](C1)N2C)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

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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
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
Health Status: healthy
Age Group: 21.4 years
Sex: M
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
Health Status: healthy
Age Group: 22.8 years
Sex: M
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)
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
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
Health Status: unhealthy
Age Group: 83 years
Sex: F
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
Health Status: healthy
Age Group: adult
Sex: M
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
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
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
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
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
Health Status: healthy
Age Group: 21 - 47 years
Sex: M+F
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
Health Status: healthy
Age Group: 21.4 years
Sex: M
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
Health Status: healthy
Age Group: 21.4 years
Sex: M
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)
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
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)
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
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)
Health Status: healthy
Age Group: 24 years (range: 19-38 years)
Sex: M
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
Health Status: unhealthy
Age Group: 83 years
Sex: F
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
Health Status: unhealthy
Age Group: 83 years
Sex: F
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
Effects of physostigmine, scopolamine, and mecamylamine on the sleeping time induced by ketamine in the rat.
1979 Mar 14
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
Scopolamine-induced convulsions in food given fasted mice: effects of clonidine and tizanidine.
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
The ameliorating effects of the cognitive-enhancing Chinese herbs on scopolamine-induced amnesia in rats.
2000 Aug
Serial position effect and selective amnesia induced by scopolamine in mice.
2000 Feb
Dehydroevodiamine.HCl prevents impairment of learning and memory and neuronal loss in rat models of cognitive disturbance.
2000 Jan
Intra-medial prefrontal cortex injections of scopolamine increase instrumental responses for cocaine: an intravenous self-administration study in rats.
2000 Jan 15
Antiamnesic effect of metoprine and of selective histamine H(1) receptor agonists in a modified mouse passive avoidance test.
2000 Jul 7
Probing peripheral and central cholinergic system responses.
2000 Sep
Muscarinic cholinergic and glutamatergic reciprocal regulation of expression of hippocampal cholinergic neurostimulating peptide precursor protein gene in rat hippocampus.
2001
Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats.
2001 Apr
Decreased scopolamine yield in field-grown Duboisia plants regenerated from hairy roots.
2001 Apr
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.
2001 Apr 13
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
Inhaled anticholinergic therapy: applied pharmacology and interesting developments.
2001 Jan
Enterostatin (VPDPR) has anti-analgesic and anti-amnesic activities.
2001 Jan
[Frey syndrome].
2001 Jan
Sexual diergism in rat hypothalamic-pituitary-adrenal axis responses to cholinergic stimulation and antagonism.
2001 Jan 1
Effects of the 5-HT(6) receptor antagonist Ro 04-6790 on learning consolidation.
2001 Jan 8
Developmental exposure to methylmercury alters behavioral sensitivity to D-amphetamine and pentobarbital in adult rats.
2001 Jan-Feb
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
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
Morphological and functional in vitro and in vivo characterization of the mouse corpus cavernosum.
2001 Mar
Scopolamine reduces the P35m and P60m deflections of the human somatosensory evoked magnetic fields.
2001 Mar 5
Memory impairment induced by cholinergic antagonists injected into the mushroom bodies of the honeybee.
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
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms.
2001 May
Excitatory nicotinic and desensitizing muscarinic (M2) effects on C-nociceptors in isolated rat skin.
2001 May 1
Release of non-neuronal acetylcholine from the human placenta: difference to neuronal acetylcholine.
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
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on Mon Mar 31 20:50:49 GMT 2025
Edited
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on Mon Mar 31 20:50:49 GMT 2025
Record UNII
HO322TV6PV
Record Status Validated (UNII)
Record Version
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Name Type Language
N-BUTYRYL SCOPOLAMINE
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.))-
Preferred Name English
N-BUTYRYLSCOPOLAMINE
Common Name English
Code System Code Type Description
FDA UNII
HO322TV6PV
Created by admin on Mon Mar 31 20:50:49 GMT 2025 , Edited by admin on Mon Mar 31 20:50:49 GMT 2025
PRIMARY
CAS
740757-65-7
Created by admin on Mon Mar 31 20:50:49 GMT 2025 , Edited by admin on Mon Mar 31 20:50:49 GMT 2025
PRIMARY
PUBCHEM
71587791
Created by admin on Mon Mar 31 20:50:49 GMT 2025 , Edited by admin on Mon Mar 31 20:50:49 GMT 2025
PRIMARY
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