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MedKoo Cat#: 318252 | Name: Methscopolamine bromide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methylscopolamine is an oral medication used along with other medications to treat peptic ulcers by reducing stomach acid secretion. Proton pump inhibitors and antihistamine medications have made this use obsolete. It can also be used for stomach or intestinal spasms, to reduce salivation, and to treat motion sickness. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold, irritable bowel syndrome and allergy medications.

Chemical Structure

Methscopolamine bromide
Methscopolamine bromide
CAS#155-41-9 (bromide)

Theoretical Analysis

MedKoo Cat#: 318252

Name: Methscopolamine bromide

CAS#: 155-41-9 (bromide)

Chemical Formula: C18H24BrNO4

Exact Mass: 0.0000

Molecular Weight: 398.30

Elemental Analysis: C, 54.28; H, 6.07; Br, 20.06; N, 3.52; O, 16.07

Price and Availability

Size Price Availability Quantity
500mg USD 250.00 2 Weeks
1g USD 450.00 2 Weeks
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Related CAS #
13265-10-6 (cation) 155-41-9 (bromide) 6106-46-3 (nitrate)
Synonym
Methscopolamine bromide, N-methyl scopolamine, DD-234, Pamine, Scopolamine Methyl Bromide, NSC 61809, NSC 120606, U-5036
IUPAC/Chemical Name
(1R,2R,4S,5S,7s)-7-(((S)-3-hydroxy-2-phenylpropanoyl)oxy)-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-9-ium bromide
InChi Key
CXYRUNPLKGGUJF-RAFJPFSSSA-M
InChi Code
InChI=1S/C18H24NO4.BrH/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11;/h3-7,12-17,20H,8-10H2,1-2H3;1H/q+1;/p-1/t12-,13-,14-,15+,16-,17+;/m1./s1
SMILES Code
C[N+]1(C)[C@@]2([H])[C@@]3([H])O[C@@]3([H])[C@]1([H])C[C@H](OC([C@@H](C4=CC=CC=C4)CO)=O)C2.[Br-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C20M08C06
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Methscopolamine is a muscarinic acetylcholine receptor blocker.
In vitro activity:
The orthosteric antagonists quinuclidinyl benzilate (QNB) and N-methylscopolamine (NMS) bind to the binding pocket of the muscarinic acetylcholine receptor formed by transmembrane α-helices. The affinity of NMS at the allosteric site is in the micromolar range for all receptor subtypes. Reference: Sci Rep. 2017 Jan 16;7:40381. https://pubmed.ncbi.nlm.nih.gov/28091608/
In vivo activity:
This paper reports that the muscarine antagonist methscopolamine, injected unilaterally into the nucleus accumbens, induced predominantly contralateral rotation in monoaminergically intact mice. In monoamine-depleted animals intra-accumbens methscopolamine induced only a weak stimulation of rotational behaviour (not significant), but the direction of the rotation was exclusively contralateral, and the animals showed contralateral body deviation. Reference: J Neural Transm Gen Sect. 1995;101(1-3):149-57. https://pubmed.ncbi.nlm.nih.gov/8695045/
Solvent mg/mL mM comments
Solubility
DMF 5.0 12.55
DMSO 42.0 105.45
PBS (pH 7.2) 10.0 25.11
Water 79.0 198.34
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 398.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Jakubík J, Randáková A, Zimčík P, El-Fakahany EE, Doležal V. Binding of N-methylscopolamine to the extracellular domain of muscarinic acetylcholine receptors. Sci Rep. 2017 Jan 16;7:40381. doi: 10.1038/srep40381. PMID: 28091608; PMCID: PMC5238504. 2. Novi F, Scarselli M, Corsini GU, Maggio R. An unusual form of the association binding kinetics of N-[3H]methylscopolamine to the split muscarinic M2trunk/M2tail receptor. J Pharmacol Exp Ther. 2003 May;305(2):786-95. doi: 10.1124/jpet.102.045393. Epub 2003 Jan 24. PMID: 12606698. 3. Oki T, Takagi Y, Inagaki S, Taketo MM, Manabe T, Matsui M, Yamada S. Quantitative analysis of binding parameters of [3H]N-methylscopolamine in central nervous system of muscarinic acetylcholine receptor knockout mice. Brain Res Mol Brain Res. 2005 Jan 5;133(1):6-11. doi: 10.1016/j.molbrainres.2004.09.012. PMID: 15661360. 4. Svensson A, Carlsson ML. The muscarine antagonist methscopolamine and the NMDA antagonist AP-5 injected unilaterally into the nucleus accumbens cause mice to rotate in opposite directions. J Neural Transm Gen Sect. 1995;101(1-3):149-57. doi: 10.1007/BF01271552. PMID: 8695045.
In vitro protocol:
1. Jakubík J, Randáková A, Zimčík P, El-Fakahany EE, Doležal V. Binding of N-methylscopolamine to the extracellular domain of muscarinic acetylcholine receptors. Sci Rep. 2017 Jan 16;7:40381. doi: 10.1038/srep40381. PMID: 28091608; PMCID: PMC5238504. 2. Novi F, Scarselli M, Corsini GU, Maggio R. An unusual form of the association binding kinetics of N-[3H]methylscopolamine to the split muscarinic M2trunk/M2tail receptor. J Pharmacol Exp Ther. 2003 May;305(2):786-95. doi: 10.1124/jpet.102.045393. Epub 2003 Jan 24. PMID: 12606698.
In vivo protocol:
1. Oki T, Takagi Y, Inagaki S, Taketo MM, Manabe T, Matsui M, Yamada S. Quantitative analysis of binding parameters of [3H]N-methylscopolamine in central nervous system of muscarinic acetylcholine receptor knockout mice. Brain Res Mol Brain Res. 2005 Jan 5;133(1):6-11. doi: 10.1016/j.molbrainres.2004.09.012. PMID: 15661360. 2. Svensson A, Carlsson ML. The muscarine antagonist methscopolamine and the NMDA antagonist AP-5 injected unilaterally into the nucleus accumbens cause mice to rotate in opposite directions. J Neural Transm Gen Sect. 1995;101(1-3):149-57. doi: 10.1007/BF01271552. PMID: 8695045.
1: Oki T, Takagi Y, Inagaki S, Taketo MM, Manabe T, Matsui M, Yamada S. Quantitative analysis of binding parameters of [3H]N-methylscopolamine in central nervous system of muscarinic acetylcholine receptor knockout mice. Brain Res Mol Brain Res. 2005 Jan 5;133(1):6-11. PubMed PMID: 15661360. 2: Novi F, Scarselli M, Corsini GU, Maggio R. An unusual form of the association binding kinetics of N-[3H]methylscopolamine to the split muscarinic M2trunk/M2tail receptor. J Pharmacol Exp Ther. 2003 May;305(2):786-95. Epub 2003 Jan 24. PubMed PMID: 12606698. 3: Krejcí A, Tucek S. Changes of cooperativity between N-methylscopolamine and allosteric modulators alcuronium and gallamine induced by mutations of external loops of muscarinic M(3) receptors. Mol Pharmacol. 2001 Oct;60(4):761-7. PubMed PMID: 11562438. 4: Lazareno S, Birdsall B, Fukazawa T, Gharagozloo P, Hashimoto T, Kuwano H, Popham A, Sugimoto M, Birdsall NJ. Allosteric effects of four stereoisomers of a fused indole ring system with 3H-N-methylscopolamine and acetylcholine at M1-M4 muscarinic receptors. Life Sci. 1999;64(6-7):519-26. PubMed PMID: 10069518. 5: Taghavi E, Menkes DB, Howard RC, Mason PA, Shaw JP, Spears GF. Premenstrual syndrome: a double-blind controlled trial of desipramine and methylscopolamine. Int Clin Psychopharmacol. 1995 Jun;10(2):119-22. PubMed PMID: 7673655. 6: Golovko AI, Sofronov GA, Kurganova TA, Kliuntina TV. [The effect of paraoxon and sulfhydryl reagents on the binding of 3H-quinuclidinyl benzilate and 3H-methylscopolamine with synaptic membranes of rat cerebral cortex]. Biull Eksp Biol Med. 1994 Jul;118(7):51-3. Russian. PubMed PMID: 7919274. 7: Flynn DD, Mash DC. Distinct kinetic binding properties of N-[3H]-methylscopolamine afford differential labeling and localization of M1, M2, and M3 muscarinic receptor subtypes in primate brain. Synapse. 1993 Aug;14(4):283-96. PubMed PMID: 8248852. 8: Pakarinen ED, Moerschbaecher JM. Comparison of the effects of scopolamine and methylscopolamine on the performance of a fixed-ratio discrimination in squirrel monkeys. Pharmacol Biochem Behav. 1993 Apr;44(4):815-9. PubMed PMID: 8469694. 9: Kvaltínová Z, Juránek I, Machová J, Stolc S. Effect of oxidative stress on (3H)N-methylscopolamine binding and production of thiobarbituric acid reactive substances in rat cerebral cortex membranes. Gen Physiol Biophys. 1993 Apr;12(2):155-61. PubMed PMID: 8405918. 10: Viana GS, Sousa FC, Marinho MM. Effect of mazindol administration on (3H)-N-methylscopolamine binding to rat cerebral cortex. Life Sci. 1992;50(8):549-53. PubMed PMID: 1736025. 11: Aoki E, Adachi H, Noguchi M, Satoh S, Ohnishi S, Honda T, Konishi J. [Analysis of muscarinic receptors on rat pancreatic acini by using 125I-quinuclidinyl benzilate and N-[3H]-methylscopolamine]. Nihon Shokakibyo Gakkai Zasshi. 1991 Aug;88(8):1571-8. Japanese. PubMed PMID: 1942611. 12: Alonso R, Didier M, Soubrie P. [3H]N-methylscopolamine binding studies reveal M2 and M3 muscarinic receptor subtypes on cerebellar granule cells in primary culture. J Neurochem. 1990 Jul;55(1):334-7. PubMed PMID: 2355226. 13: Eva C, Ferrero P, Rocca P, Funaro A, Bergamasco B, Ravizza L, Genazzani E. [3H]N-methylscopolamine binding to muscarinic receptors in human peripheral blood lymphocytes: characterization, localization on T-lymphocyte subsets and age-dependent changes. Neuropharmacology. 1989 Jul;28(7):719-26. PubMed PMID: 2788247. 14: van Haaren F, van Hest A, van Hattum T. Scopolamine and methylscopolamine differentially affect fixed-consecutive-number performance of male and female Wistar rats. Pharmacol Biochem Behav. 1989 Jun;33(2):361-5. PubMed PMID: 2813474. 15: Eller M, Järv J. Kinetics of N-methylscopolamine interaction with muscarinic receptor from rat cerebral cortex. Neurochem Int. 1989;15(3):301-5. PubMed PMID: 20504498. 16: Lüllmann H, Mohr K, Pfeffer J. Release of N-[3H]methylscopolamine from isolated guinea pig atria is controlled by diffusion and rebinding. J Pharmacol Exp Ther. 1988 Nov;247(2):710-4. PubMed PMID: 3183965. 17: Jepsen K, Lüllmann H, Mohr K, Pfeffer J. Allosteric stabilization of 3H-N-methylscopolamine binding in guinea-pig myocardium by an antidote against organophosphate intoxication. Pharmacol Toxicol. 1988 Sep;63(3):163-8. PubMed PMID: 3054859. 18: Ensing K, Bloemhof DA, in 't Hout WG, de Zeeuw RA. Discrepancies in the specific activity of 3H-N-methylscopolamine as determined by mass spectrometry and radioreceptor assay due to racemisation. J Recept Res. 1988;8(6):871-83. PubMed PMID: 3193405. 19: Cymerman U, Palacios JM, Cortés R, Skangiel-Kramska J. Autoradiographic localization of muscarinic cholinergic receptors in visual areas of cat brain: variations in sensitivity of N-[3H]methylscopolamine binding sites to carbachol and pirenzepine. Neurosci Lett. 1987 Oct 16;81(1-2):13-8. PubMed PMID: 3696462. 20: Lynch JJ, Nelson SD, MacEwen SA, Driscoll EM, Lucchesi BR. Antifibrillatory efficacy of concomitant beta adrenergic receptor blockade with dilevalol, the R,R-isomer of labetalol, and muscarinic receptor blockade with methylscopolamine. J Pharmacol Exp Ther. 1987 May;241(2):741-9. PubMed PMID: 2883307.