L-(+)-Abrine

Names

[ CAS No. ]:
526-31-8

[ Name ]:
L-(+)-Abrine

[Synonym ]:
a-Methylamino-b-(3-indole)propionic Acid
N-ME-TRYPTOPHAN
L-N-Methyltryptophan
N-Methyl-L-tryptophan
L-Tryptophan, N-methyl-
H-METRP-OH
L-Abrine
Abrine
L-2-methyltryptophan
EINECS 208-388-5
ABRINE,L
N-methyl-tryptophan
N-α-Methyl-L-trytophan
N(α)-methyl-L-tryptophan
N(α)-methyl-L-tryptophan zwitterion
N(alpha)-methyl-L-tryptophan
MFCD00005645
Nα-Methyl-L-tryptophan
N-ME-TRP-OH HCL
N-ME-TRP-OH

Biological Activity

[Description]:

L-(+)-Abrine, a lethal albumin found in Abrus precatorius seeds, is an acute toxic alkaloid and chemical marker for abrin.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Alkaloid

Research Areas >> Others

[In Vitro]

L-(+)-Abrine is a marker for abrin poisoning. A strong indication for abrin poisoning is the presence of the chemical maker L-(+)-Abrine, which can survive metabolism in significant amounts making it detectable in human urine[1].

[In Vivo]

Abrin is a toxic protein found in the jequirity seed. L-(+)-Abrine (L-Abrine) is also found in the jequirity seed and can be used as a biomarker for abrin exposure. An animal study is designed to monitor the excretion and recovery of L-(+)-Abrine in 20 rats. The animals are exposed to one of three concentrations of L-(+)-Abrine, a single high concentration of L-tryptophan, or no agent (control). The low L-(+)-Abrine dose corresponds to 0.63 LD50 i.p. abrin in mice, assuming a concentration ratio of 1:4 of abrin to L-(+)-Abrine and an LD50 for abrin of 20 μg/kg. The mid and high L-(+)-Abrine (250 and 400 μg/kg) doses are included to ensure that the target analyte can be detected and tracked over the course of the experiment[2].

[Animal admin]

Rats[2] Twenty male Wistar rats, approximately 6-7 weeks of age and weighing approximately 175-200 g upon receipt, are used. A total of 12 rats are dosed intramuscularly with L-(+)-Abrine at 0.63, 3.13, and 5 times the expected Abrin LD50 of 20 μg/kg. Although no toxin is used here, the concentration of the biomarker is increased by a factor of 4 to estimate an equivalent level of toxin, assuming that Labrine is present in rosary peas at a concentration four times greater that the toxin abrin. A total of 12 rats are dosed intramuscularly with L-(+)-Abrine: four at approximately 50 μg/kg body weight (bw), four at 250 μg/kg bw, and four at 400 μg/kg bw. Four control rats are dosed with water, which is the vehicle for all dosing experiments. Another four rats are dosed intraperitoneally with 20,000 μg/kg L-tryptophan to verify that endogenous L-tryptophan is not metabolized to L-(+)-Abrine[2].

[References]

[1]. Cho H, et al. A portable and chromogenic enzyme-based sensor for detection of abrin poisoning. Biosens Bioelectron. 2014 Apr 15;54:667-73.

[2]. Johnson RC, et al. Quantification of L-abrine in human and rat urine: a biomarker for the toxin abrin. J Anal Toxicol. 2009 Mar;33(2):77-84.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
439.1±35.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₂H₁₄N₂O₂

[ Molecular Weight ]:
218.252

[ Flash Point ]:
219.4±25.9 °C

[ Exact Mass ]:
218.105530

[ PSA ]:
65.12000

[ LogP ]:
1.18

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.649

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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