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

MedKoo CAT#: 571393

CAS#: 526-31-8

Description: Abrine is an alkaloid chemical marker and surrogate analyte of abrin, a group of highly toxic glycoproteins. Abrine can be used as a marker for abrin in various consumer products and foods.


Chemical Structure

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Abrine
CAS# 526-31-8

Theoretical Analysis

MedKoo Cat#: 571393
Name: Abrine
CAS#: 526-31-8
Chemical Formula: C12H14N2O2
Exact Mass: 218.1055
Molecular Weight: 218.26
Elemental Analysis: C, 66.04; H, 6.47; N, 12.84; O, 14.66

Price and Availability

Size Price Availability Quantity
200.0mg USD 200.0 2 Weeks
1.0g USD 365.0 2 Weeks
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Synonym: Abrine

IUPAC/Chemical Name: N-Methyl-L-tryptophan

InChi Key: CZCIKBSVHDNIDH-NSHDSACASA-N

InChi Code: InChI=1S/C12H14N2O2/c1-13-11(12(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,11,13-14H,6H2,1H3,(H,15,16)/t11-/m0/s1

SMILES Code: O=C(O)[C@H](CC1=CNC2=C1C=CC=C2)NC

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

Preparing Stock Solutions

The following data is based on the product molecular weight 218.26 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

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1: Dodge AG, Carrasquillo K, Rivera L, Xu L, Wackett LP, Sadowsky MJ. Rapid method using two microbial enzymes for detection of L-abrine in food as a marker for the toxic protein abrin. Appl Environ Microbiol. 2015 Mar;81(5):1610-5. doi: 10.1128/AEM.03492-14. Epub 2014 Dec 19. PubMed PMID: 25527549; PubMed Central PMCID: PMC4325171.

2: Wooten JV, Pittman CT, Blake TA, Thomas JD, Devlin JJ, Higgerson RA, Johnson RC. A case of abrin toxin poisoning, confirmed via quantitation of L-abrine (N-methyl-L-tryptophan) biomarker. J Med Toxicol. 2014 Dec;10(4):392-4. doi: 10.1007/s13181-013-0377-9. PubMed PMID: 24522983; PubMed Central PMCID: PMC4252293.

3: Owens J, Koester C. Quantitation of abrine, an indole alkaloid marker of the toxic glycoproteins abrin, by liquid chromatography/tandem mass spectrometry when spiked into various beverages. J Agric Food Chem. 2008 Dec 10;56(23):11139-43. doi: 10.1021/jf802471y. PubMed PMID: 19007169.

4: Johnson RC, Zhou Y, Jain R, Lemire SW, Fox S, Sabourin P, Barr JR. Quantification of L-abrine in human and rat urine: a biomarker for the toxin abrin. J Anal Toxicol. 2009 Mar;33(2):77-84. PubMed PMID: 19239732.

5: Yang M, Al Zaharna M, Chen YS, Li L, Cheung HY. In vitro antioxidant activities and anti-proliferative properties of the functional herb Abrus cantoniensis and its main alkaloid abrine. Food Funct. 2014 Sep;5(9):2268-77. doi: 10.1039/c4fo00217b. PubMed PMID: 25059572.

6: Chen KC, Chen CY. In Silico Identification of Potent PPAR-γ Agonists from Traditional Chinese Medicine: A Bioactivity Prediction, Virtual Screening, and Molecular Dynamics Study. Evid Based Complement Alternat Med. 2014;2014:192452. doi: 10.1155/2014/192452. Epub 2014 May 26. PubMed PMID: 24971147; PubMed Central PMCID: PMC4058246.

7: Danner P, Morkunas M, Maier ME. Synthesis of D-abrines by palladium-catalyzed reaction of ortho-iodoanilines with N-Boc-N-methylalanyl-substituted acetaldehyde and acetylene. Org Lett. 2013 May 17;15(10):2474-7. doi: 10.1021/ol4009409. Epub 2013 Apr 30. PubMed PMID: 23631420; PubMed Central PMCID: PMC3823808.

8: Cho H, Jaworski J. A portable and chromogenic enzyme-based sensor for detection of abrin poisoning. Biosens Bioelectron. 2014 Apr 15;54:667-73. doi: 10.1016/j.bios.2013.11.058. Epub 2013 Nov 27. PubMed PMID: 24334282.

9: Lee WY, Chen KC, Chen HY, Chen CY. Potential mitochondrial isocitrate dehydrogenase R140Q mutant inhibitor from traditional Chinese medicine against cancers. Biomed Res Int. 2014;2014:364625. doi: 10.1155/2014/364625. Epub 2014 Jun 5. PubMed PMID: 24995286; PubMed Central PMCID: PMC4066711.

10: Pinto Nde C, Duque AP, Pacheco NR, Mendes Rde F, Motta EV, Bellozi PM, Ribeiro A, Salvador MJ, Scio E. Pereskia aculeata: A plant food with antinociceptive activity. Pharm Biol. 2015;53(12):1780-5. doi: 10.3109/13880209.2015.1008144. Epub 2015 Jun 18. PubMed PMID: 26084799.

11: Richou R, Lallouette P, Richou H. [Contribution to the study of the modifications of inflammatory reactions, induced by abrine, in guinea pigs immunized with ana-abrine]. C R Acad Sci Hebd Seances Acad Sci D. 1966 Jul 18;263(3):308-9. French. PubMed PMID: 4961223.

12: Ruan HL, Stec E, Li SM. Production of diprenylated indole derivatives by tandem incubation of two recombinant dimethylallyltryptophan synthases. Arch Microbiol. 2009 Oct;191(10):791-5. doi: 10.1007/s00203-009-0504-9. Epub 2009 Sep 1. PubMed PMID: 19727673.

13: Hung TC, Chen KB, Huang HJ, Chen CY. Lead Screening for HIV of C-C Chemokine Receptor Type 5 Receptor Inhibited by Traditional Chinese Medicine. Evid Based Complement Alternat Med. 2014;2014:313094. doi: 10.1155/2014/313094. Epub 2014 Apr 30. PubMed PMID: 24876870; PubMed Central PMCID: PMC4021832.

14: Steffan N, Unsöld IA, Li SM. Chemoenzymatic synthesis of prenylated indole derivatives by using a 4-dimethylallyltryptophan synthase from Aspergillus fumigatus. Chembiochem. 2007 Jul 23;8(11):1298-307. PubMed PMID: 17577899.

15: DIACONO H. [Not Available]. Ann Pharm Fr. 1949 Nov;7(11):655-9. Undetermined Language. PubMed PMID: 15404664.

16: Rigbers O, Li SM. Ergot alkaloid biosynthesis in Aspergillus fumigatus. Overproduction and biochemical characterization of a 4-dimethylallyltryptophan N-methyltransferase. J Biol Chem. 2008 Oct 3;283(40):26859-68. doi: 10.1074/jbc.M804979200. Epub 2008 Aug 4. PubMed PMID: 18678866.

17: Herraiz T, Galisteo J. Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. Free Radic Res. 2004 Mar;38(3):323-31. PubMed PMID: 15129740.

18: Zhu HJ, Jiang JX, Saebo S, Pittman CU Jr. Chiral ligands derived from Abrine 8. An experimental and theoretical study of free ligand conformational preferences and the addition of diethylzinc to benzaldehyde. J Org Chem. 2005 Jan 7;70(1):261-7. PubMed PMID: 15624931.

Abrine

200.0mg / USD 200.0