Hyoscyamine

• CAT Number: A000309
• CAS Number: 101-31-5
• Molecular Formula: C17H23NO3
• Molecular Weight: 289.37
• Purity: ≥95%
• Target: AChR
• Solubility: Soluble in DMSO > 10 mM
• Storage: -20°C
• InChI: 1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16-/m1/s1
• InChIKey: RKUNBYITZUJHSG-VFSICIBPSA-N
• SMILES: CN1C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3

It is a non-selective antagonist at Muscarinic receptors, levorotary isomer of Atropine


Tropane alkaloid<!–C17H23NO3–>, from the plant Datura stramonium, Solanaceae.

As compared with the activity of Atropine, Hyoscyamine is 1.5 – 2 times as potent on the circular ocular muscle, 3 times as potent on the heart cholinoreceptors and 10 times as potent on the intestine cholinoreceptors.

Reference

1: Khan MS, Tiwari A, Khan Z, Sharma H, Taleb M, Hammersley J. Pyridostigmine
Induced Prolonged Asystole in a Patient with Myasthenia Gravis Successfully
Treated with Hyoscyamine. Case Rep Cardiol. 2017;2017:6956298. doi:
10.1155/2017/6956298. Epub 2017 May 14. PubMed PMID: 28589042; PubMed Central
PMCID: PMC5446877.

2: Moharrami F, Hosseini B, Sharafi A, Farjaminezhad M. Enhanced production of
hyoscyamine and scopolamine from genetically transformed root culture of
Hyoscyamus reticulatus L. elicited by iron oxide nanoparticles. In Vitro Cell Dev
Biol Plant. 2017;53(2):104-111. doi: 10.1007/s11627-017-9802-0. Epub 2017 Feb 27.
PubMed PMID: 28553065; PubMed Central PMCID: PMC5423962.

3: Qiang W, Hou YL, Li X, Xia K, Liao ZH. [Cloning and expression of the key
enzyme hyoscyamine 6 beta-hydroxylase gene (DaH6H) in scopolamine biosynthesis of
Datura arborea]. Yao Xue Xue Bao. 2015 Oct;50(10):1346-55. Chinese. PubMed PMID:
26837185.

4: Zaazaa HE, Salama NN, Abd El Halim LM, Salem MY, Abd El Fattah LE. Strategy
Approach for Direct Enantioseparation of Hyoscyamine Sulfate and Zopiclone on a
Chiral αl-Acid Glycoprotein Column and Determination of Their Eutomers:
Thermodynamic Study of Complexation. Chirality. 2016 Jan;28(1):49-57. doi:
10.1002/chir.22536. Epub 2015 Nov 3. PubMed PMID: 26527388.

5: Dziomba S, Łepek T, Jaremicz Z, Łuczkiewicz M, Prahl A, Kowalski P.
Simultaneous determination of scopolamine, hyoscyamine and anisodamine in in
vitro growth media of selected Solanaceae hairy roots by CE method. J Chromatogr
B Analyt Technol Biomed Life Sci. 2015 Sep 15;1001:17-21. doi:
10.1016/j.jchromb.2015.06.029. Epub 2015 Jul 22. PubMed PMID: 26253806.

6: Cao YD, He YC, Li H, Kai GY, Xu JH, Yu HL. Efficient biosynthesis of rare
natural product scopolamine using E. coli cells expressing a S14P/K97A mutant of
hyoscyamine 6β-hydroxylase AaH6H. J Biotechnol. 2015 Oct 10;211:123-9. doi:
10.1016/j.jbiotec.2015.07.019. Epub 2015 Jul 31. PubMed PMID: 26239231.

7: Cheng C, Lau JE, Earl MA. Use of atropine-diphenoxylate compared with
hyoscyamine to decrease rates of irinotecan-related cholinergic syndrome. J
Community Support Oncol. 2015 Jan;13(1):3-7. doi: 10.12788/jcso.0099. PubMed
PMID: 25839059.

8: Naumann A, Kurtze L, Krähmer A, Hagels H, Schulz H. Discrimination of
Solanaceae taxa and quantification of scopolamine and hyoscyamine by ATR-FTIR
spectroscopy. Planta Med. 2014 Oct;80(15):1315-20. doi: 10.1055/s-0034-1383046.
Epub 2014 Sep 23. PubMed PMID: 25248046.

9: Mulder PP, von Holst C, Nivarlet N, van Egmond HP. Intra- and inter-laboratory
validation of a dipstick immunoassay for the detection of tropane alkaloids
hyoscyamine and scopolamine in animal feed. Food Addit Contam Part A Chem Anal
Control Expo Risk Assess. 2014;31(7):1165-76. doi: 10.1080/19440049.2014.914249.
Epub 2014 May 14. PubMed PMID: 24823431.

10: Ghobrial PM, Neuberger I, Guglielmo FF, Mitchell DG, Parker L, O/’Kane PL,
Roth CG, Deshmukh SP, Borowski A. Cine MR enterography grading of small bowel
peristalsis: evaluation of the antiperistaltic effectiveness of sublingual
hyoscyamine sulfate. Acad Radiol. 2014 Jan;21(1):86-91. doi:
10.1016/j.acra.2013.09.024. PubMed PMID: 24331269.