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Merck
CN

S7882

(−)-Scopolamine N-butyl bromide

≥98% (TLC), powder

Synonym(s):

(−)-N-Butylscopolamine bromide, Hyoscine N-butyl bromide

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About This Item

Empirical Formula (Hill Notation):
C21H30BrNO4
CAS Number:
149-64-4
Molecular Weight:
440.37
NACRES:
NA.77
PubChem Substance ID:
24277872
UNSPSC Code:
12352116
EC Number:
205-744-1
MDL number:
MFCD00078561

Key Documents

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InChI key

HOZOZZFCZRXYEK-GSWUYBTGSA-M

InChI

1S/C21H30NO4.BrH/c1-3-4-10-22(2)17-11-15(12-18(22)20-19(17)26-20)25-21(24)16(13-23)14-8-6-5-7-9-14;/h5-9,15-20,23H,3-4,10-13H2,1-2H3;1H/q+1;/p-1/t15-,16-,17-,18+,19-,20+,22?;/m1./s1

SMILES string

[Br-].[H][C@@]12C[C@H](C[C@@]([H])([C@]3([H])O[C@]13[H])[N+]2(C)CCCC)OC(=O)[C@H](CO)c4ccccc4

assay

≥98% (TLC)

form

powder

optical activity

[α]25/D −20.8°, c = 3 in H2O(lit.)

color

white

solubility

H2O: 50 mg/mL

Quality Level

100

Gene Information

human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)

Application

(−)-Scopolamine N-butyl bromide was used as standard in designing a procedure for quantification of compounds using CE-MS.8

Biochem/physiol Actions

Competitive muscarinic acetylcholine receptor antagonist; antispasmodic.
Scopolamine is an anti-muscarinic and cholinolytic alkaloid that inhibits parasympathetic-cholinergic system.5 The central effects include hallucinations, disorientation, restlessness and euphoria.6 Scopolamine disturb the stimulus detection performance in rats by interfering with the reticular cholinergic pathways.7

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1443
BCCK9400
BCCG9318
BCCD7058
BCCB8329

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S Lin et al.
Digestive diseases and sciences, 42(5), 907-914 (1997-05-01)
Expression of muscarinic receptor subtypes in rat gastric smooth muscle was examined with reverse transcriptase-polymerase chain reaction (RT-PCR). Under the condition for detecting the messages of m1-m4 subtypes in brain, atrium, and gastric mucosa, only the fragments of m2 and
K Kurahashi et al.
Life sciences, 61(8), 831-838 (1997-01-01)
The inhibitory effects of atropine, cimetropium, pirenzepine and N-butylscopolamine on the vagal afferent gastric excitatory response in cats under anesthesia with pentobarbital sodium and infusion of gallamine were examined. Electrical stimulation of vagal trunk in left side (10 Hz in
Jens Ohnesorge et al.
Electrophoresis, 26(12), 2360-2375 (2005-06-01)
Different approaches were chosen to examine ionization reproducibility of analytes after separation by capillary electrophoresis-mass spectrometry (CE-MS) in a commercially available sheath-flow electrospray interface. For this task three different standard samples were examined. Sample 1 contained neostigmine bromide (cationic), paracetamol
Yuki Himoto et al.
International journal of gynecological cancer : official journal of the International Gynecological Cancer Society, 25(6), 1079-1085 (2015-04-09)
To assess the prognostic impact of the pretreatment mean apparent diffusion coefficient (ADCmean) values of tumors obtained by diffusion-weighted magnetic resonance imaging. We evaluated the prognostic value of the ADCmean for event-free survival (EFS) and overall survival (OS) among patients
Nanda Venkatanarasimha et al.
European journal of radiology, 82(4), 583-588 (2012-12-26)
To assess the effect of parenteral butylscopolamine on magnetic resonance cholangiopancreatography (MRCP) image quality. The 3D free-breathing respiratory-compensated MRCP images (mean acquisition time 7min) of 94 consecutive non-paired patients (47 with and 47 without 20mg intramuscular butylscopolamine) were analysed retrospectively.
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