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A9546

Sigma-Aldrich

2-Amino-6-methylmercaptopurine

≥95%

Synonyme(s) :

2-Amino-6-methylthiopurine

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About This Item

Formule empirique (notation de Hill):
C6H7N5S
Numéro CAS:
1198-47-6
Poids moléculaire :
181.22
Numéro CE :
214-833-4
Numéro MDL:
MFCD00044701
Code UNSPSC :
41106305
ID de substance PubChem :
24891471
Nomenclature NACRES :
NA.51

Pureté

≥95%

Forme

solid

Chaîne SMILES 

[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)

Clé InChI

YEGKYFQLKYGHAR-UHFFFAOYSA-N

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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.

Actions biochimiques/physiologiques

2-Amino-6-methylmercaptopurine is synthesized from 6-mercaptopurine by the S methylation activity of thiopurine methyl transferase (TMPT) enzyme.

Pictogrammes

CorrosionExclamation mark
GHS05,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H315,H318,H335

Classification des risques

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Sigma-Aldrich

MAK308

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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
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)
Bifeng Yuan et al.
ACS chemical biology, 5(11), 1021-1027 (2010-09-03)
Thiopurines are effective immunosuppressants and anticancer agents. However, the long-term use of thiopurines was found to be associated with a significantly increased risk of various types of cancer. To date, the specific mechanism(s) underlying the carcinogenicity associated with thiopurine treatment
Hongxia Wang et al.
Analytical chemistry, 82(13), 5797-5803 (2010-06-17)
Thiopurines, including mercaptopurine (MP), 6-thioguanine ((S)G) and azathioprine, are widely used for the treatment of many human diseases including acute lymphoblastic leukemia (ALL). To exert their cytotoxic effect, these prodrugs need to be metabolically activated to (S)G nucleotides and incorporated
Loretta T Ford et al.
Annals of clinical biochemistry, 41(Pt 4), 303-308 (2004-08-10)
Although widely used, thiopurine drugs have a narrow therapeutic index and treatment can result in life-threatening toxicity, the basis being pharmacogenetic variation in thiopurine metabolism by thiopurine S-methyltransferase (TPMT). We recently developed a modified phenotyping assay to determine TPMT activity
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