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MedKoo Cat#: 592752 | Name: Amabiline

Description:

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

Amabiline is an antimalarial alkaloid.

Chemical Structure

Amabiline
Amabiline
CAS#17958-43-9

Theoretical Analysis

MedKoo Cat#: 592752

Name: Amabiline

CAS#: 17958-43-9

Chemical Formula: C16H19NO4

Exact Mass: 289.1314

Molecular Weight: 289.33

Elemental Analysis: C, 66.42; H, 6.62; N, 4.84; O, 22.12

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
Amabiline
IUPAC/Chemical Name
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1H-pyrrolidizin-7-yl)methyl ester
InChi Key
DLYIURZCCWSUKD-MPESAESLSA-N
InChi Code
InChI=1S/C16H19NO4/c18-11-1-2-14-16(15(11)19)3-4-17(14)7-9-5-12-13(6-10(9)16)21-8-20-12/h5-6,11,14-15,18-19H,1-4,7-8H2/t11-,14-,15-,16+/m1/s1
SMILES Code
InChI=1S/C16H19NO4/c18-11-1-2-14-16(15(11)19)3-4-17(14)7-9-5-12-13(6-10(9)16)21-8-20-12/h5-6,11,14-15,18-19H,1-4,7-8H2/t11-,14-,15-,16+/m1/s1
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 289.33 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: Senter TJ, Fadeyi OO, Lindsley CW. Enantioselective total synthesis of (+)-amabiline. Org Lett. 2012 Apr 6;14(7):1869-71. doi: 10.1021/ol300466a. Epub 2012 Mar 20. PubMed PMID: 22432912; PubMed Central PMCID: PMC3359844. 2: Findlay AD, Banwell MG. A chemoenzymatic total synthesis of (+)-amabiline. Org Lett. 2009 Jul 16;11(14):3160-2. doi: 10.1021/ol901230w. PubMed PMID: 19586069. 3: Boppré M, Colegate SM. Recognition of pyrrolizidine alkaloid esters in the invasive aquatic plant Gymnocoronis spilanthoides (Asteraceae). Phytochem Anal. 2015 May-Jun;26(3):215-25. doi: 10.1002/pca.2555. Epub 2015 Jan 27. PubMed PMID: 25645745. 4: Likhitwitayawuid K, Angerhofer CK, Chai H, Pezzuto JM, Cordell GA, Ruangrungsi N. Cytotoxic and antimalarial alkaloids from the bulbs of Crinum amabile. J Nat Prod. 1993 Aug;56(8):1331-8. PubMed PMID: 8229016. 5: Letsyo E, Jerz G, Winterhalter P, Horn G, Beuerle T. Survey of pyrrolizidine alkaloids in seven varieties of Lappula squarrosa: An alternative source of heart-healthy vegetable oil. Phytochem Anal. 2016 Mar-Apr;27(2):133-9. doi: 10.1002/pca.2608. PubMed PMID: 26895990. 6: Edgar JA, Lin HJ, Kumana CR, Ng MM. Pyrrolizidine alkaloid composition of three Chinese medicinal herbs, Eupatorium cannabinum, E. japonicum and Crotalaria assamica. Am J Chin Med. 1992;20(3-4):281-8. PubMed PMID: 1471612. 7: Hendriks H, Balraadjsing W, Huizing HJ, Bruins AP. Investigation into the Presence of Pyrrolizidine Alkaloids in Eupatorium cannabinum by Means of Positive and Negative Ion Chemical Ionization GC-MS. Planta Med. 1987 Oct;53(5):456-61. PubMed PMID: 17269067. 8: Wiedenfeld H, Guerrero R, Roeder E. Pyrrolizidine alkaloids from Eupatorium portoricense. Planta Med. 1995 Aug;61(4):380-1. PubMed PMID: 17238090. 9: Trigo JR, Witte L, Brown KS Jr, Hartmann T, Barata LE. Pyrrolizidine alkaloids in the arctiid mothHyalurga syma. J Chem Ecol. 1993 Apr;19(4):669-79. doi: 10.1007/BF00985000. PubMed PMID: 24249009. 10: Williams MT, Warnock BJ, Betz JM, Beck JJ, Gardner DR, Lee ST, Molyneux RJ, Colegate SM. Detection of high levels of pyrrolizidine-N-oxides in the endangered plant Cryptantha crassipes (Terlingua Creek cat's-eye) using HPLC-ESI-MS. Phytochem Anal. 2011 Nov-Dec;22(6):532-40. doi: 10.1002/pca.1314. Epub 2011 Mar 24. PubMed PMID: 21433162. 11: Trigo JR, Barata LE, Brown KS Jr. Stereochemical inversion of pyrrolizidine alkaloids byMechanitis polymnia (Lepidoptera: Nymphalidae: Ithomiinae): Specificity and evolutionary significance. J Chem Ecol. 1994 Nov;20(11):2883-99. doi: 10.1007/BF02098396. PubMed PMID: 24241922. 12: Verma P, Chandra A, Pandey G. Diversity-Oriented Approach Toward the Syntheses of Amaryllidaceae Alkaloids via a Common Chiral Synthon. J Org Chem. 2018 Jul 26. doi: 10.1021/acs.joc.8b01368. [Epub ahead of print] PubMed PMID: 30005155.