A9546
2-Amino-6-methylmercaptopurine
≥95%
Synonym(s):
2-Amino-6-methylthiopurine
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About This Item
Empirical Formula (Hill Notation):
C6H7N5S
CAS Number:
Molecular Weight:
181.22
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
214-833-4
MDL number:
Assay:
≥95%
Form:
solid
Quality Level
assay
≥95%
form
solid
SMILES string
[H]n1cnc2c(SC)nc(N)nc12
InChI
1S/C6H7N5S/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
InChI key
YEGKYFQLKYGHAR-UHFFFAOYSA-N
Application
2-Amino-6-methylmercaptopurine (6-MTG) has been used as a supplement in Dulbecco′s modified Eagles medium (DMEM) medium for the selection of gpt-expressing recombinant virus mCMVhMIEPE-gpt.lacZ (cytomegalovirus major immediate-early promotor-enhancer complex-gpt.lacz). It has also been used as a standard in high performance liquid chromatography (HPLC) to assess the activity of thiopurine methyltransferase (TPMT) enzyme.
2-Amino-6-methylmercaptopurine is a 2-amino-6-alkyldithiopurine that has been used with other 6-position carbon analogues to study brain specific diazepam binding.
Biochem/physiol Actions
2-Amino-6-methylmercaptopurine is synthesized from 6-mercaptopurine by the S methylation activity of thiopurine methyl transferase (TMPT) enzyme.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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G R Erdmann et al.
Journal of chromatography, 571(1-2), 149-156 (1991-11-15)
A reversed-phase high-performance liquid chromatographic (HPLC) procedure was developed to quantify intracellular lymphocyte 6-thioguanine, methylmercaptopurine and methylthioguanine. The free base of each metabolite was obtained by acid hydrolysis, which allowed for a total determination of thiopurine metabolites. 6-Thioguanine was analyzed
Pharmacogenetics of drug metabolizing enzyme: thiopurine methyl transferase phenotypes and multidrug resistance 1 gene polymorphism in inflammatory bowel disease
Bahrehmand F, et al.
Cellular and Molecular Biology, 62(7), 102-109 (2016)
Cancer Chemotherapy and Biotherapy: Principles and Practice, 193-193 (2010)
T Dooley et al.
Journal of chromatography, 337(2), 321-327 (1985-02-08)
A flow-fluorimetric high-performance liquid chromatographic assay for 6-methylthioguanine in urine has been developed. This compound is a major catabolite of 6-thioguanine, an important drug in cancer chemotherapy. The metabolite was extracted from alkaline urine with ethyl acetate which was injected
T R Waters et al.
Biochemistry, 36(9), 2501-2506 (1997-03-04)
It has been suggested that the cytotoxicity of 6-thioguanine depends upon (1) incorporation of 6-thioguanine into DNA, (2) methylation by S-adenosylmethionine (SAM) of the thio group to give S6-methylthioguanine, (3) miscoding during DNA replication to give [SMeG] x T base
Global Trade Item Number
| SKU | GTIN |
|---|---|
| A9546-100MG | 04061833045381 |
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