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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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