Aminopterin

SIGMA/A1784 - powder

Synonym: (S)-2-{4-[(2,4-Diaminopteridin-6-yl)methylamino]benzamido}pentanedioic acid; 4-Amino-PGA; 4-Aminofolic acid; 4-Aminopteroyl-L-glutamic acid

CAS Number: 54-62-6
Empirical Formula (Hill Notation): C₁₉H₂₀N₈O₅
Molecular Weight: 440.41
EC Number: 200-209-9
MDL Number: MFCD00036692
Linear Formula: C₁₉H₂₀N₈O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-A1784-50MG	50 mg	$393.00 1/EA	Add To Favorites
45-A1784-100MG	100 mg	$626.00 1/EA	Add To Favorites
45-A1784-1G	1 g	$3020.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A1784-1G

Properties
Descriptions
Safety Info.
Basic Data

ε (extinction coefficient)	24,500 at 282 nm in 0.1 M NaOH at 1 M
	25,700 at 261 nm in 0.1 M NaOH at 1 M
	8,100 at 373 nm in 0.1 M NaOH at 1 M
assay	≥97% (TLC)
biological source	synthetic (organic)
color	yellow
form	powder
InChI	1S/C19H20N8O5/c20-15-14-16(27-19(21)26-15)23-8-11(24-14)7-22-10-3-1-9(2-4-10)17(30)25-12(18(31)32)5-6-13(28)29/h1-4,8,12,22H,5-7H2,(H,25,30)(H,28,29)(H,31,32)(H4,20,21,23,26,27)/t12-/m0/s1
InChI key	TVZGACDUOSZQKY-LBPRGKRZSA-N
mp	225 °C
Quality Level	200
SMILES string	Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1
solubility	2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.)
	DMSO: soluble (Solutions may be stored for 1-2 days at 4°C.)
storage temp.	−20°C

Biochem/physiol Actions:	Folic acid antagonist that binds to dihydrofolate reductase and inhibits its activity.
Biochem/physiol Actions:	Folic acid antagonist. Aminopterin is actively transported into cells by the folate transporter. In the cell, it is converted to a high molecular weight polyglutamate metabolite by folylpolyglutamate synthase that, in turn, binds to dihydrofolate reductase and inhibits its activity. Aminopterin-polyglutamate is degraded intracellularly by γ-glutamyl hydrolase.
Features and Benefits:	This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
Other Notes:	More potent, but more toxic, than methotrexate.
Packaging:	1 g in glass bottle
Packaging:	50 mg in glass bottle

Symbol	GHS06,GHS08
Signal word	Danger
Hazard statements	H300 - H360FD
Precautionary statements	P201 - P202 - P264 - P270 - P280 - P301 + P310
Hazard Codes	T+
Risk Statements	61-28
Safety Statements	53-28-36/37-45
RIDADR	UN 2811 6.1 / PGI
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥97% (TLC)
mp	225 °C
Storage Temp.	−20°C
UNSPSC	12352200

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