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MedKoo Cat#: 318001 | Name: Hyoscyamine
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Description:

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

Hyoscyamine is a tropane alkaloid. It is a secondary metabolite found in certain plants of the Solanaceae family. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine. Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.

Chemical Structure

Hyoscyamine
Hyoscyamine
CAS#101-31-5 (free)

Theoretical Analysis

MedKoo Cat#: 318001

Name: Hyoscyamine

CAS#: 101-31-5 (free)

Chemical Formula: C17H23NO3

Exact Mass: 289.1678

Molecular Weight: 289.38

Elemental Analysis: C, 70.56; H, 8.01; N, 4.84; O, 16.59

Price and Availability

Size Price Availability Quantity
500mg USD 350.00 2 Weeks
1g USD 550.00 2 Weeks
5g USD 900.00 2 Weeks
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Related CAS #
6835-16-1 (sulfate) 306-03-6 (HBr) 101-31-5 (free)
Synonym
Hyoscyamine; Cystospaz; L-Atropine; Levsin; L-Hyopscyamine; L-Hyoscamine; Hyoscyamine Hydrochloride; Hyoscyamine Sulfate; Hyoscyamine Sulfate Anhydrous; Symax; HyoMax; Anaspaz; Egazil; Buwecon;
IUPAC/Chemical Name
(8-methyl-8-azabicyclo[3.2.1]octan-3-yl) (2S)-3-hydroxy-2-phenylpropanoate
InChi Key
RKUNBYITZUJHSG-LGGPCSOHSA-N
InChi Code
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
SMILES Code
O=C(OC1CC(N2C)CCC2C1)[C@@H](C3=CC=CC=C3)CO
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
Instruction
View handling instruction
Biological target:
L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205).
In vitro activity:
TBD
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMSO 79.0 273.00
Ethanol 58.0 200.43
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 289.38 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:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: 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. 2: 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. 3: Jaremicz Z, Luczkiewicz M, Kisiel M, Zárate R, El Jaber-Vazdekis N, Migas P. Multi-development-HPTLC method for quantitation of hyoscyamine, scopolamine and their biosynthetic precursors in selected solanaceae plants grown in natural conditions and as in vitro cultures. Phytochem Anal. 2014 Jan-Feb;25(1):29-35. doi: 10.1002/pca.2455. Epub 2013 Jul 9. PubMed PMID: 23839972. 4: 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. 5: 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. 6: 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. 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: 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. 9: Nguyen TK, Jamali A, Lanoue A, Gontier E, Dauwe R. Unravelling the architecture and dynamics of tropane alkaloid biosynthesis pathways using metabolite correlation networks. Phytochemistry. 2015 Aug;116:94-103. doi: 10.1016/j.phytochem.2015.03.005. Epub 2015 Mar 27. PubMed PMID: 25823585. 10: Dehghan E, Shahriari Ahmadi F, Ghotbi Ravandi E, Reed DW, Covello PS, Bahrami AR. An atypical pattern of accumulation of scopolamine and other tropane alkaloids and expression of alkaloid pathway genes in Hyoscyamus senecionis. Plant Physiol Biochem. 2013 Sep;70:188-94. doi: 10.1016/j.plaphy.2013.05.007. Epub 2013 May 18. PubMed PMID: 23786817. 11: 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. 12: Zhang XQ, Luo ZW, Zhang H, Wang FY, Sun JW, Sun M. [Scopolamine and hyoscyamine synthesis in hair roots culture of Datura metel]. Zhongguo Zhong Yao Za Zhi. 2012 Nov;37(21):3223-8. Chinese. PubMed PMID: 23397717. 13: Qiang W, Wang YX, Zhang QZ, Li JD, Xia K, Wu NB, Liao ZH. [Expression pattern of genes involved in tropane alkaloids biosynthesis and tropane alkaloids accumulation in Atropa belladonna]. Zhongguo Zhong Yao Za Zhi. 2014 Jan;39(1):52-8. Chinese. PubMed PMID: 24754168. 14: Ryad A, Lakhdar K, Majda KS, Samia A, Mark A, Corinne AD, Eric G. Optimization of the culture medium composition to improve the production of hyoscyamine in elicited Datura stramonium L. hairy roots using the Response Surface Methodology (RSM). Int J Mol Sci. 2010 Nov 18;11(11):4726-40. doi: 10.3390/ijms11114726. PubMed PMID: 21151467; PubMed Central PMCID: PMC3000111. 15: Simões PM, Niven JE, Ott SR. Phenotypic transformation affects associative learning in the desert locust. Curr Biol. 2013 Dec 2;23(23):2407-12. doi: 10.1016/j.cub.2013.10.016. Epub 2013 Nov 21. PubMed PMID: 24268415; PubMed Central PMCID: PMC4024192. 16: Li J, van Belkum MJ, Vederas JC. Functional characterization of recombinant hyoscyamine 6β-hydroxylase from Atropa belladonna. Bioorg Med Chem. 2012 Jul 15;20(14):4356-63. doi: 10.1016/j.bmc.2012.05.042. Epub 2012 May 26. PubMed PMID: 22705021. 17: Kai G, Zhang A, Guo Y, Li L, Cui L, Luo X, Liu C, Xiao J. Enhancing the production of tropane alkaloids in transgenic Anisodus acutangulus hairy root cultures by over-expressing tropinone reductase I and hyoscyamine-6β-hydroxylase. Mol Biosyst. 2012 Nov;8(11):2883-90. doi: 10.1039/c2mb25208b. Epub 2012 Sep 6. PubMed PMID: 22955966. 18: Long Z, Wang C, Guo Z, Zhang X, Nordahl L, Zeng J, Zeng J, Liang X. A non-aqueous solid phase extraction method for alkaloid enrichment and its application in the determination of hyoscyamine and scopolamine. Analyst. 2012 Mar 21;137(6):1451-7. doi: 10.1039/c2an15824h. Epub 2012 Feb 2. PubMed PMID: 22299130. 19: Long SP, Lu Y, Wang YX, Yang CX, Lan XZ, Liao ZH. [Enhancement of tropane alkaloids production in transgenic hair roots of Atropa belladonna by overexpressing endogenous genes AbPMT and AbH6H]. Yao Xue Xue Bao. 2013 Feb;48(2):243-9. Chinese. PubMed PMID: 23672021. 20: Antoine Lanfranchi D, Tomi F, Casanova J. Enantiomeric differentiation of atropine/hyoscyamine by (13) C NMR spectroscopy and its application to Datura stramonium extract. Phytochem Anal. 2010 Nov-Dec;21(6):597-601. doi: 10.1002/pca.1240. Epub 2010 Aug 26. PubMed PMID: 20799269.