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MedKoo Cat#: 462646 | Name: β-Methylamino-L-Alanine

Description:

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

β-Methylamino-L-alanine is a neurotoxic non-proteinogenic amino acid that has been found in cyanobacteria. It is cytotoxic to mouse primary cortical neurons when used at a concentration of 3 mM in the presence of bicarbonate, an effect that can be blocked by the NMDA receptor antagonist MK-801 or the mGluR5 receptor antagonist MPEP.

Chemical Structure

β-Methylamino-L-Alanine
β-Methylamino-L-Alanine
CAS#16012-55-8

Theoretical Analysis

MedKoo Cat#: 462646

Name: β-Methylamino-L-Alanine

CAS#: 16012-55-8

Chemical Formula: C4H11ClN2O2

Exact Mass: 154.0509

Molecular Weight: 154.59

Elemental Analysis: C, 31.08; H, 7.17; Cl, 22.93; N, 18.12; O, 20.70

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 #
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Synonym
BMAA; L-BMAA; LBMAA; L BMAA;
IUPAC/Chemical Name
(S)-2-amino-3-(methylamino)propanoic acid hydrochloride
InChi Key
VDXYGASOGLSIDM-DFWYDOINSA-N
InChi Code
InChI=1S/C4H10N2O2.ClH/c1-6-2-3(5)4(7)8;/h3,6H,2,5H2,1H3,(H,7,8);1H/t3-;/m0./s1
SMILES Code
N[C@@H](CNC)C(O)=O.[H]Cl
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 154.59 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: Spencer PS, Palmer VS, Kisby GE. Cycad β-N-methylamino-L-alanine (BMAA), methylazoxymethanol, genotoxicity, and neurodegeneration. Toxicon. 2018 Dec 1;155:49-50. doi: 10.1016/j.toxicon.2018.10.005. Epub 2018 Oct 11. PMID: 30316979. 2: Dunlop RA, Guillemin GJ. The Cyanotoxin and Non-protein Amino Acid β-Methylamino-L-Alanine (L-BMAA) in the Food Chain: Incorporation into Proteins and Its Impact on Human Health. Neurotox Res. 2019 Oct;36(3):602-611. doi: 10.1007/s12640-019-00089-9. Epub 2019 Aug 3. PMID: 31377995. 3: Proctor EA, Mowrey DD, Dokholyan NV. β-Methylamino-L-alanine substitution of serine in SOD1 suggests a direct role in ALS etiology. PLoS Comput Biol. 2019 Jul 19;15(7):e1007225. doi: 10.1371/journal.pcbi.1007225. PMID: 31323035; PMCID: PMC6668853. 4: Rauk A. β- N-Methylamino-l-alanine (BMAA) Not Involved in Alzheimer's Disease. J Phys Chem B. 2018 Apr 26;122(16):4472-4480. doi: 10.1021/acs.jpcb.8b01641. Epub 2018 Apr 17. PMID: 29649877. 5: Violi JP, Facey JA, Mitrovic SM, Colville A, Rodgers KJ. Production of β-methylamino-L-alanine (BMAA) and Its Isomers by Freshwater Diatoms. Toxins (Basel). 2019 Sep 2;11(9):512. doi: 10.3390/toxins11090512. PMID: 31480725; PMCID: PMC6784237. 6: Okamoto S, Esumi S, Hamaguchi-Hamada K, Hamada S. β-N-methylamino-L-alanine (BMAA) suppresses cell cycle progression of non-neuronal cells. Sci Rep. 2018 Dec 20;8(1):17995. doi: 10.1038/s41598-018-36418-9. PMID: 30573743; PMCID: PMC6301973. 7: van Onselen R, Venables L, van de Venter M, Downing TG. β-N-Methylamino-L- Alanine Toxicity in PC12: Excitotoxicity vs. Misincorporation. Neurotox Res. 2018 Jan;33(1):15-23. doi: 10.1007/s12640-017-9743-8. Epub 2017 May 3. PMID: 28470567. 8: Han NC, Bullwinkle TJ, Loeb KF, Faull KF, Mohler K, Rinehart J, Ibba M. The mechanism of β-N-methylamino-l-alanine inhibition of tRNA aminoacylation and its impact on misincorporation. J Biol Chem. 2020 Jan 31;295(5):1402-1410. doi: 10.1074/jbc.RA119.011714. Epub 2019 Dec 20. PMID: 31862734; PMCID: PMC6996898. 9: Kokubo Y, Banack SA, Morimoto S, Murayama S, Togashi T, Metcalf JS, Cox PA, Kuzuhara S. β-N-methylamino-l-alanine analysis in the brains of patients with Kii ALS/PDC. Neurology. 2017 Sep 5;89(10):1091-1092. doi: 10.1212/WNL.0000000000004310. Epub 2017 Aug 9. PMID: 28794246. 10: Contardo-Jara V, Schwanemann T, Esterhuizen-Londt M, Pflugmacher S. Protein association of β-N-methylamino-L-alanine in Triticum aestivum via irrigation. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Apr;35(4):731-739. doi: 10.1080/19440049.2018.1427283. Epub 2018 Jan 25. PMID: 29324084. 11: Bishop SL , Murch SJ . A systematic review of analytical methods for the detection and quantification of β-N-methylamino-l-alanine (BMAA). Analyst. 2019 Dec 16;145(1):13-28. doi: 10.1039/c9an01252d. PMID: 31742261. 12: Cheng F, Fransson LÅ, Mani K. The cyanobacterial neurotoxin β-N-methylamino- l-alanine prevents addition of heparan sulfate to glypican-1 and increases processing of amyloid precursor protein in dividing neuronal cells. Exp Cell Res. 2019 Jun 15;379(2):172-181. doi: 10.1016/j.yexcr.2019.03.041. Epub 2019 Apr 3. PMID: 30953622. 13: Regueiro J, Negreira N, Carreira-Casais A, Pérez-Lamela C, Simal-Gándara J. Dietary exposure and neurotoxicity of the environmental free and bound toxin β-N-methylamino-l-alanine. Food Res Int. 2017 Oct;100(Pt 1):1-13. doi: 10.1016/j.foodres.2017.07.033. Epub 2017 Jul 20. PMID: 28873667. 14: Meneely JP, Chevallier OP, Graham S, Greer B, Green BD, Elliott CT. β-methylamino-L-alanine (BMAA) is not found in the brains of patients with confirmed Alzheimer's disease. Sci Rep. 2016 Nov 8;6:36363. doi: 10.1038/srep36363. PMID: 27821863; PMCID: PMC5099567. 15: Delcourt N, Claudepierre T, Maignien T, Arnich N, Mattei C. Cellular and Molecular Aspects of the β-N-Methylamino-l-alanine (BMAA) Mode of Action within the Neurodegenerative Pathway: Facts and Controversy. Toxins (Basel). 2017 Dec 22;10(1):6. doi: 10.3390/toxins10010006. PMID: 29271898; PMCID: PMC5793093. 16: Waidyanatha S, Ryan K, Sanders JM, McDonald JD, Wegerski CJ, Doyle-Eisle M, Garner CE. Disposition of β-N-methylamino-l-alanine (L-BMAA), a neurotoxin, in rodents following a single or repeated oral exposure. Toxicol Appl Pharmacol. 2018 Jan 15;339:151-160. doi: 10.1016/j.taap.2017.12.008. Epub 2017 Dec 15. PMID: 29248465. 17: Popova AA, Koksharova OA. Neurotoxic Non-proteinogenic Amino Acid β-N- Methylamino-L-alanine and Its Role in Biological Systems. Biochemistry (Mosc). 2016 Aug;81(8):794-805. doi: 10.1134/S0006297916080022. PMID: 27677549. 18: Yan B, Liu Z, Huang R, Xu Y, Liu D, Wang W, Zhao Z, Cui F, Shi W. Impact factors on the production of β-methylamino-L-alanine (BMAA) by cyanobacteria. Chemosphere. 2020 Mar;243:125355. doi: 10.1016/j.chemosphere.2019.125355. Epub 2019 Nov 14. PMID: 31759214. 19: Scott LL, Downing TG. Β-N-Methylamino-L-Alanine (BMAA) Toxicity Is Gender and Exposure-Age Dependent in Rats. Toxins (Basel). 2017 Dec 27;10(1):16. doi: 10.3390/toxins10010016. PMID: 29280981; PMCID: PMC5793103. 20: Downing S, Van Onselen R, Kemp G, Downing TG. Metabolism of the neurotoxic amino acid β-N-methylamino-L-alanine in human cell culture models. Toxicon. 2019 Oct;168:131-139. doi: 10.1016/j.toxicon.2019.07.007. Epub 2019 Jul 19. PMID: 31330193.