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Merck
CN

A9546

Sigma-Aldrich

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:
1198-47-6
Molecular Weight:
181.22
EC Number:
214-833-4
MDL number:
MFCD00044701
UNSPSC Code:
41106305
PubChem Substance ID:
24891471
NACRES:
NA.51

Key Documents

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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

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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.

Biochem/physiol Actions

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

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H315,H318,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
081H0183

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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
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
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
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