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MedKoo Cat#: 599041 | Name: Littorine

Description:

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

Littorine is a tropane alkaloid found in a variety of plants including Datura and Atropa belladonna. It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway.

Chemical Structure

Littorine
CAS#21956-47-8

Theoretical Analysis

MedKoo Cat#: 599041

Name: Littorine

CAS#: 21956-47-8

Chemical Formula: C17H23NO3

Exact Mass: 289.1678

Molecular Weight: 289.37

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

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 #
No Data
Synonym
Littorine; (R)-(-)-Littorine;
IUPAC/Chemical Name
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-3-phenylpropanoate
InChi Key
FNRXUEYLFZLOEZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)11-15(10-13)21-17(20)16(19)9-12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3
SMILES Code
O=C(OC1CC(N2C)CCC2C1)C(O)CC3=CC=CC=C3
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 289.37 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: Li R, Reed DW, Liu E, Nowak J, Pelcher LE, Page JE, Covello PS. Functional genomic analysis of alkaloid biosynthesis in Hyoscyamus niger reveals a cytochrome P450 involved in littorine rearrangement. Chem Biol. 2006 May;13(5):513-20. PubMed PMID: 16720272. 2: Nasomjai P, Reed DW, Tozer DJ, Peach MJ, Slawin AM, Covello PS, O'Hagan D. Mechanistic insights into the cytochrome P450-mediated oxidation and rearrangement of littorine in tropane alkaloid biosynthesis. Chembiochem. 2009 Sep 21;10(14):2382-93. doi: 10.1002/cbic.200900318. PubMed PMID: 19693762. 3: Al Balkhi MH, Schiltz S, Lesur D, Lanoue A, Wadouachi A, Boitel-Conti M. Norlittorine and norhyoscyamine identified as products of littorine and hyoscyamine metabolism by (13)C-labeling in Datura innoxia hairy roots. Phytochemistry. 2012 Feb;74:105-14. doi: 10.1016/j.phytochem.2011.10.010. Epub 2011 Nov 13. PubMed PMID: 22083085. 4: Mateus L, Cherkaoui S, Christen P, Oksman-Caldentey KM. Simultaneous determination of scopolamine, hyoscyamine and littorine in plants and different hairy root clones of Hyoscyamus muticus by micellar electrokinetic chromatography. Phytochemistry. 2000 Jun;54(5):517-23. PubMed PMID: 10939356. 5: Lanoue A, Boitel-Conti M, Portais JC, Laberche JC, Barbotin JN, Christen P, Sangwan-Norreel B. Kinetic study of littorine rearrangement in Datura innoxia hairy roots by (13)C NMR spectroscopy. J Nat Prod. 2002 Aug;65(8):1131-5. PubMed PMID: 12193016. 6: Griffin WJ, Lin GD. The isolation of littorine from a Duboisia hybrid. Naturwissenschaften. 1989 Dec;76(12):582. PubMed PMID: 2622482. 7: 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. 8: Kennington WJ, Lukehurst SS, Johnson MS. Characterization of microsatellite loci for the littorine snail Bembicium vittatum. Mol Ecol Resour. 2008 Nov;8(6):1463-5. doi: 10.1111/j.1755-0998.2008.02247.x. Epub 2008 Sep 15. PubMed PMID: 21586077. 9: Patterson S, O'Hagan D. Biosynthetic studies on the tropane alkaloid hyoscyamine in Datura stramonium; hyoscyamine is stable to in vivo oxidation and is not derived from littorine via a vicinal interchange process. Phytochemistry. 2002 Oct;61(3):323-9. PubMed PMID: 12359518. 10: Layer G, Kervio E, Morlock G, Heinz DW, Jahn D, Retey J, Schubert WD. Structural and functional comparison of HemN to other radical SAM enzymes. Biol Chem. 2005 Oct;386(10):971-80. Review. PubMed PMID: 16218869. 11: Duran-Patron R, O'Hagan D, Hamilton JT, Wong CW. Biosynthetic studies on the tropane ring system of the tropane alkaloids from Datura stramonium. Phytochemistry. 2000 Apr;53(7):777-84. PubMed PMID: 10783983. 12: Cui L, Huang F, Zhang D, Lin Y, Liao P, Zong J, Kai G. Transcriptome exploration for further understanding of the tropane alkaloids biosynthesis in Anisodus acutangulus. Mol Genet Genomics. 2015 Aug;290(4):1367-77. doi: 10.1007/s00438-015-1005-y. Epub 2015 Feb 10. PubMed PMID: 25876163. 13: Mateus L, Cherkaoui S, Christen P, Veuthey JL. Enantioseparation of atropine by capillary electrophoresis using sulfated beta-cyclodextrin: application to a plant extract. J Chromatogr A. 2000 Feb 4;868(2):285-94. PubMed PMID: 10701678. 14: Bedewitz MA, Góngora-Castillo E, Uebler JB, Gonzales-Vigil E, Wiegert-Rininger KE, Childs KL, Hamilton JP, Vaillancourt B, Yeo YS, Chappell J, DellaPenna D, Jones AD, Buell CR, Barry CS. A root-expressed L-phenylalanine:4-hydroxyphenylpyruvate aminotransferase is required for tropane alkaloid biosynthesis in Atropa belladonna. Plant Cell. 2014 Sep;26(9):3745-62. doi: 10.1105/tpc.114.130534. Epub 2014 Sep 16. PubMed PMID: 25228340; PubMed Central PMCID: PMC4213168. 15: Schmeller T, Sporer F, Sauerwein M, Wink M. Binding of tropane alkaloids to nicotinic and muscarinic acetylcholine receptors. Pharmazie. 1995 Jul;50(7):493-5. PubMed PMID: 7675895. 16: Ollagnier S, Kervio E, Rétey J. The role and source of 5'-deoxyadenosyl radical in a carbon skeleton rearrangement catalyzed by a plant enzyme. FEBS Lett. 1998 Oct 23;437(3):309-12. PubMed PMID: 9824314. 17: Sandala GM, Smith DM, Radom L. The carbon-skeleton rearrangement in tropane alkaloid biosynthesis. J Am Chem Soc. 2008 Aug 13;130(32):10684-90. doi: 10.1021/ja801869a. Epub 2008 Jul 16. PubMed PMID: 18627156. 18: Kamardin NN. [Probable structural functional evolution of sensory surface of osphradia of aquatic prosobranchian molluscs]. Zh Evol Biokhim Fiziol. 2014 Nov-Dec;50(6):470-8. Russian. PubMed PMID: 25782289. 19: Humphrey AJ, O'Hagan D. Tropane alkaloid biosynthesis. A century old problem unresolved. Nat Prod Rep. 2001 Oct;18(5):494-502. PubMed PMID: 11699882. 20: John H, Binder T, Höchstetter H, Thiermann H. LC-ESI MS/MS quantification of atropine and six other antimuscarinic tropane alkaloids in plasma. Anal Bioanal Chem. 2010 Jan;396(2):751-63. doi: 10.1007/s00216-009-3209-7. Epub 2009 Oct 25. PubMed PMID: 19855962.

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