Skip to Content
Merck
CN

Key Documents

View All Documentation

A1784

Aminopterin

synthetic (organic), ≥97% (TLC), dihydrofolate reductase inhibitor, powder

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C19H20N8O5
CAS Number:
54-62-6
Molecular Weight:
440.41
MDL number:
MFCD00036692
UNSPSC Code:
12352200
PubChem Substance ID:
24278186
NACRES:
NA.77
EC Number:
200-209-9
Beilstein/REAXYS Number:
69045
Form:
powder
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Aminopterin, powder

biological source

synthetic (organic)

Quality Segment

200

description

Purity (≥98%)

form

powder

color

light yellow to yellow-brown

solubility

2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.)

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

storage temp.

−20°C

SMILES string

Nc1nc(N)c2nc(CNc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1

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

Gene Information

human ... FPGS(2356)
mouse ... Fpgs(14287)

Biochem/physiol Actions

Folic acid antagonist that binds to dihydrofolate reductase and inhibits its activity.
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.

Still not finding the right product?

Explore all of our products under Aminopterin

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 Oral - Eye Irrit. 2 - Muta. 2 - Repr. 1B - Skin Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000509269
0000509269
0000490219
0000490219
0000490215

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Articles

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Folic Acid Metabolism in Cancer

Cancer research innovations address the complexity of the disease, providing advanced technologies for varied applications.

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

View All Articles

Global Trade Item Number

SKUGTIN
A1784-100MG04061833020241
A1784-50MG04061833342992
A1784-1G04061833342985