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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

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

signalword

Danger

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A Practical Non-Extraction Direct Liquid Chromatography Method for Determination of Thiopurine S-Methyltransferase Activity in Inflammatory Bowel Disease
Bahrehmand F, et al.
Acta Medica Iranica, 55(6), 360-367 (2017)
Effect of 9-alkyl derivatives of 6-methylthioguanine on brain specific binding of [3H]diazepam.
S C Sung et al.
Biochemical pharmacology, 35(20), 3645-3646 (1986-10-15)
S C Sung et al.
Biochemical pharmacology, 33(11), 1737-1739 (1984-06-01)
Various derivatives of 2-amino-6- methylthiopurine with substituents at the 6-position of purine were tested for their abilities to displace [3H]diazepam binding to rat brain membranes. The potency was dependent on the carbon chain-length in the 6-position of purine. Among the
P F Swann et al.
Science (New York, N.Y.), 273(5278), 1109-1111 (1996-08-23)
It is proposed here that the delayed cytotoxicity of thioguanine involves the postreplicative DNA mismatch repair system. After incorporation into DNA, the thioguanine is chemically methylated by S-adenosylmethionine to form S6-methylthioguanine. During DNA replication, the S6-methylthioguanine directs incorporation of either
S C Sung et al.
European journal of pharmacology, 81(3), 505-508 (1982-07-16)
We have compared fifteen synthetic purines and purine nucleosides on their ability to displace [3H]diazepam binding to rat brain membranes. Among these analogs, 6-methylthioguanine was found to be most potent, inhibiting competitively the specific binding of [3H]diazepam with a Ki
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