N-Butylscopolammonium bromide - CAS 149-64-4

Catalog number: BRP-02095

N-Butylscopolammonium bromide

N-Butylscopolammonium bromide is a peripherally acting antimuscarinic and anticholinergic agent.

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Ordering Information
Catalog Number Size Price Stock Quantity
BRP-02095 10 g $199 In stock
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Catalog
BRP-02095
Synonyms
Scopolamine butylbromide; Hyoscine butylbromide; Scopolan; Butylscopolammonium bromide; Butylscopolamine bromide; 3-Oxa-9-azoniatricyclo[3.3.1.02,4]nonane, 9-butyl-7-[(2S)-3-hydroxy-1-oxo-2-phenylpropoxy]-9-methyl-, bromide (1:1), (1α,2β,4β,5α,7β)-; 1αH,5αH-Tropanium, 8-butyl-6β,7β-epoxy-3α-hydroxy-, bromide, (-)-tropate; 3-Oxa-9-azoniatricyclo[3.3.1.0 ]nonane, 9-butyl7-(3-hydroxy-1-oxo-2-phenylpropoxy)-9-methyl-, bromide, [7(S)-(1α,2β,4β,5α,7β)]-; (-)-Scopolamine butylbromide; Amisepan; Buscapine; Buscol; Buscolamin; Buscolysin; Buscolysine; Buscopan; Butylmin; Donopon; Hyoscine butobromide; Joscine; Monospan; N-Butylhyoscine bromide; N-Butylhyoscinium bromide; N-Butylscopolamine bromide; N-Butylscopolaminium bromide; Scobro; Scobron; Scobutil; Scobutyl; Scopolamine bromobutylate; Scopolamine butobromide; Sparicon; Sporamin; Sporamin (pharmaceutical); Stibron; Tirantil
CAS
149-64-4
IUPAC Name
(1R,2R,4S,5S,7s)-9-butyl-7-(((S)-3-hydroxy-2-phenylpropanoyl)oxy)-9-methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium;bromide
Molecular Weight
440.37
Molecular Formula
C21H30BrNO4
Canonical SMILES
[Br-].O=C(OC1CC2C3OC3C(C1)[N+]2(C)CCCC)C(C=4C=CC=CC4)CO
InChI
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
InChIKey
HOZOZZFCZRXYEK-GSWUYBTGSA-M
Melting Point
137-143 °C
Purity
>98%
Solubility
Soluble in Water
Appearance
White powder
Application
Anticholinergic/antisecretive
Storage
Store at 2-8 °C
Related CAS
7182-53-8 (free base)

Chemical Structure:

Reference Reading

1. Abuse of the over-the-counter antispasmodic butylscopolamine for the home synthesis of psychoactive scopolamine
Sebastian Kummer & Annette Rickert & Thomas Daldrup & Ertan Mayatepek. Eur J Pediatr
We present two patients who ingested homemade scopolamine leading to severe central anticholinergic effects on at least one patient. To the best of our knowledge, this is the first report in the medical literature of such a practice. Butylscopolamine (also known as butylscopolamine bromide, scopolamine butylbromide, butylhyoscine, or hyoscine butylbromide) is available as over-the-counter antispasmodic (Buscopan®) in nearly 100 countries world-wide and is included in the WHO Model List of Essential Medicines. The amount of ingested scopolamine (as estimated using the described protocol) and scopolamine concentrations measured in the patient’s serum and urine samples were in line with the published findings detailing the doses required to elicit the observed clinical symptoms. However, clinical effects are likely highly variable, given that the preparation of scopolamine was the same in both cases.
2. Anesthetic management of peroral endoscopic myotomy for esophageal achalasia: a retrospective case series
Eriko Tanaka • Hiroaki Murata • Hitomi Minami • Koji Sumikawa. J Anesth (2014) 28:456–459
Intravenous scopolamine butylbromide was administered to four patients to facilitate the POEM procedure by inhibiting abnormal spastic contraction of the esophagus. An increase in heart rate from 60 to 140 beats per min was observed in one patient, who was treated with 20 mg scopolamine butylbromide. Randiolol hydrochloride, a short-acting beta1-adrenergic antagonist, was continuously infused intravenously at a rate of 5 mcg/kg/min for about 50 min to decrease the heart rate. The remaining three patients (two received 20 mg and one received 10 mg of scopolamine butylbromide intravenously) showed a slight increase in heart rate, which lasted about 30 min, but did not require any treatment to control their heart rate. The POEM procedure achieved the decrease in lower esophageal sphincter pressure in each patient. Mean lower esophageal pressure was decreased from 71.2 to 21.0 mmHg.
3. The HepaRG cell line, a superior in vitro model to L-02, HepG2 and hiHeps cell lines for assessing drug-induced liver injury
Yu Wu & Xing-chao Geng & Ju-feng Wang & Yu-fa Miao & Yan- l i Lu & Bo Li. Cell Biol Toxicol (2016) 32:37–59
Demarcation of toxicity threshold of DILI in vitro Bambuterol hydrochloride, buspirone hydrochloride, and scopolamine butylbromide, which were defined as negative control drugs, showed no cytotoxic effects on all liver cell lines in vitro (see Fig. 1). Based on the 3 σ principles of biological statistical analysis (Wang et al.2013), we built a toxicity threshold to discriminate drugs with or without a cytotoxic effect. Moreover, the IC50 values of these three drugs were all over 1000 μMas recorded in Table 3. Toxicity threshold = x ± SD× 3, where x represents the mean value of all inhibition values of different concentrations of negative control drugs administered to different cell lines. SD means standard deviation.
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