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MedKoo Cat#: 596431 | Name: Muscarine

Description:

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

Muscarine is a toxic alkaloid found in Amanita muscaria (fly fungus) and other fungi of the Inocybe species. It is the first parasympathomimetic substance ever studied and causes profound parasympathetic activation that may end in convulsions and death. The specific antidote is atropine.

Chemical Structure

Muscarine
Muscarine
CAS#300-54-9

Theoretical Analysis

MedKoo Cat#: 596431

Name: Muscarine

CAS#: 300-54-9

Chemical Formula: C9H20NO2+

Exact Mass: 174.1489

Molecular Weight: 174.26

Elemental Analysis: C, 62.03; H, 11.57; N, 8.04; O, 18.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Muscarine; Muskarin; EINECS 206-094-1; (+)-Muscarine;
IUPAC/Chemical Name
1-((2S,4R,5S)-4-hydroxy-5-methyltetrahydrofuran-2-yl)-N,N,N-trimethylmethanaminium
InChi Key
UQOFGTXDASPNLL-XHNCKOQMSA-N
InChi Code
InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1
SMILES Code
C[C@H]1[C@H](O)C[C@@H](C[N+](C)(C)C)O1
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 174.26 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
1: Zhu Y, Dewell RB, Wang H, Gabbiani F. Pre-synaptic Muscarinic Excitation Enhances the Discrimination of Looming Stimuli in a Collision-Detection Neuron. Cell Rep. 2018 May 22;23(8):2365-2378. doi: 10.1016/j.celrep.2018.04.079. PubMed PMID: 29791848. 2: Lee MR, Dukan E, Milne I. Amanita muscaria (fly agaric): from a shamanistic hallucinogen to the search for acetylcholine. J R Coll Physicians Edinb. 2018 Mar;48(1):85-91. doi: 10.4997/JRCPE.2018.119. PubMed PMID: 29741535. 3: Yang H, Sun Q, Liang Y, Jiang Y, Li R, Ye J. Antinociception of the spirocyclopiperazinium salt compound LXM-15 via activating α7 nAChR and M4 mAChR and inhibiting CaMKIIα/cAMP/CREB/CGRP signalling pathway in mice. Regul Toxicol Pharmacol. 2018 Apr;94:108-114. doi: 10.1016/j.yrtph.2018.01.012. Epub 2018 Jan 17. PubMed PMID: 29353067. 4: Xu B, Deng H, Zhang X, Luo J, Zhang G, Zhang Z, Wang Y, Shan L. A novel Danshensu/tetramethylpyrazine derivative induces vasorelaxation on rat aorta and exerts cardioprotection in dogs. Eur J Pharmacol. 2018 Jan 5;818:158-166. doi: 10.1016/j.ejphar.2017.10.034. Epub 2017 Oct 21. PubMed PMID: 29066416. 5: Matsuoka H, Inoue M. Molecular mechanism for muscarinic M(1) receptor-mediated endocytosis of TWIK-related acid-sensitive K(+) 1 channels in rat adrenal medullary cells. J Physiol. 2017 Nov 15;595(22):6851-6867. doi: 10.1113/JP275039. Epub 2017 Oct 19. PubMed PMID: 28944482; PubMed Central PMCID: PMC5685824. 6: Cárdenas AM, Fernández-Olivares P, Díaz-Franulic I, González-Jamett AM, Shimahara T, Segura-Aguilar J, Caviedes R, Caviedes P. Knockdown of Myo-Inositol Transporter SMIT1 Normalizes Cholinergic and Glutamatergic Function in an Immortalized Cell Line Established from the Cerebral Cortex of a Trisomy 16 Fetal Mouse, an Animal Model of Human Trisomy 21 (Down Syndrome). Neurotox Res. 2017 Nov;32(4):614-623. doi: 10.1007/s12640-017-9775-0. Epub 2017 Jul 10. PubMed PMID: 28695546. 7: Dallagnol JCC, Orsato A, Ducatti DRB, Noseda MD, Duarte MER, Gonçalves AG. Aqueous semisynthesis of C-glycoside glycamines from agarose. Beilstein J Org Chem. 2017 Jun 23;13:1222-1229. doi: 10.3762/bjoc.13.121. eCollection 2017. PubMed PMID: 28694868; PubMed Central PMCID: PMC5496579. 8: Mitoh Y, Ueda H, Ichikawa H, Fujita M, Kobashi M, Matsuo R. Effects of cevimeline on excitability of parasympathetic preganglionic neurons in the superior salivatory nucleus of rats. Auton Neurosci. 2017 Sep;206:1-7. doi: 10.1016/j.autneu.2017.05.010. Epub 2017 May 30. PubMed PMID: 28600120. 9: Keshavarz M, Schwarz H, Hartmann P, Wiegand S, Skill M, Althaus M, Kummer W, Krasteva-Christ G. Caveolin-1: Functional Insights into Its Role in Muscarine- and Serotonin-Induced Smooth Muscle Constriction in Murine Airways. Front Physiol. 2017 May 15;8:295. doi: 10.3389/fphys.2017.00295. eCollection 2017. PubMed PMID: 28555112; PubMed Central PMCID: PMC5430063. 10: Doan UV, Mendez Rojas B, Kirby R. Unintentional ingestion of Cordyceps fungus-infected cicada nymphs causing ibotenic acid poisoning in Southern Vietnam. Clin Toxicol (Phila). 2017 Sep;55(8):893-896. doi: 10.1080/15563650.2017.1319066. Epub 2017 May 2. PubMed PMID: 28463017. 11: Tsentsevitsky AN, Kovyazina IV, Nurullin LF, Nikolsky EE. Muscarinic cholinoreceptors (M1-, M2-, M3- and M4-type) modulate the acetylcholine secretion in the frog neuromuscular junction. Neurosci Lett. 2017 May 10;649:62-69. doi: 10.1016/j.neulet.2017.04.015. Epub 2017 Apr 10. PubMed PMID: 28408330. 12: Vera J, Alcayaga J, Sanhueza M. Competition between Persistent Na(+) and Muscarine-Sensitive K(+) Currents Shapes Perithreshold Resonance and Spike Tuning in CA1 Pyramidal Neurons. Front Cell Neurosci. 2017 Mar 8;11:61. doi: 10.3389/fncel.2017.00061. eCollection 2017. PubMed PMID: 28337126; PubMed Central PMCID: PMC5340745. 13: Meng W, Wang S, Yao L, Zhang N, Li D. Muscarinic Receptors Are Responsible for the Cholinergic Modulation of Projection Neurons in the Song Production Brain Nucleus RA of Zebra Finches. Front Cell Neurosci. 2017 Feb 28;11:51. doi: 10.3389/fncel.2017.00051. eCollection 2017. PubMed PMID: 28293176; PubMed Central PMCID: PMC5329057. 14: Mir TA, Shinohara H. Two-Dimensional Surface Plasmon Resonance Imaging System for Cellular Analysis. Methods Mol Biol. 2017;1571:31-46. doi: 10.1007/978-1-4939-6848-0_3. PubMed PMID: 28281248. 15: Seljetun KO, von Krogh A. Acute Inocybe mushroom toxicosis in dogs: 5 cases (2010-2014). J Vet Emerg Crit Care (San Antonio). 2017 Mar;27(2):212-217. doi: 10.1111/vec.12567. Epub 2017 Feb 1. PubMed PMID: 28146341. 16: Konieczny V, Tovey SC, Mataragka S, Prole DL, Taylor CW. Cyclic AMP Recruits a Discrete Intracellular Ca(2+) Store by Unmasking Hypersensitive IP(3) Receptors. Cell Rep. 2017 Jan 17;18(3):711-722. doi: 10.1016/j.celrep.2016.12.058. PubMed PMID: 28099849; PubMed Central PMCID: PMC5276804. 17: Holt JC, Jordan PM, Lysakowski A, Shah A, Barsz K, Contini D. Muscarinic Acetylcholine Receptors and M-Currents Underlie Efferent-Mediated Slow Excitation in Calyx-Bearing Vestibular Afferents. J Neurosci. 2017 Feb 15;37(7):1873-1887. doi: 10.1523/JNEUROSCI.2322-16.2017. Epub 2017 Jan 16. PubMed PMID: 28093476; PubMed Central PMCID: PMC5320615. 18: Luo J, Liu YH, Luo W, Luo Z, Liu CT. β(2)-adrenoreceptor Inverse Agonist Down-regulates Muscarine Cholinergic Subtype-3 Receptor and Its Downstream Signal Pathways in Airway Smooth Muscle Cells in vitro. Sci Rep. 2017 Jan 4;7:39905. doi: 10.1038/srep39905. PubMed PMID: 28051147; PubMed Central PMCID: PMC5209700. 19: Ghezzi F, Corsini S, Nistri A. Electrophysiological characterization of the M-current in rat hypoglossal motoneurons. Neuroscience. 2017 Jan 6;340:62-75. doi: 10.1016/j.neuroscience.2016.10.048. Epub 2016 Oct 27. PubMed PMID: 27984184. 20: Jin Z. Muscarine, imidazole, oxazole and thiazole alkaloids. Nat Prod Rep. 2016 Oct 26;33(11):1268-1317. Review. PubMed PMID: 27714029.