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SML2832

Sigma-Aldrich

5-Amino-1-methylquinolinium iodide

≥98% (HPLC)

Synonym(s):

5-Amino-1-MQ iodide, 5-Amino-1-methylquinolinium, iodide (1:1), 5-Amino-1MQ iodide

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About This Item

Empirical Formula (Hill Notation):
C10H11N2·I
CAS Number:
42464-96-0
Molecular Weight:
286.11
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

faint red to dark brown

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

C[N+]1=CC=CC2=C(C=CC=C12)N.[I-]

InChI

1S/C10H10N2.HI/c1-12-7-3-4-8-9(11)5-2-6-10(8)12;/h2-7,11H,1H3;1H

InChI key

JPEZFBFIRRAFNR-UHFFFAOYSA-N

Biochem/physiol Actions

5-Amino-1-methylquinolinium (5-amino-1MQ) is a substrate site-targeting, selective nicotinamide N-methyltransferase (NNMT) inhibitor (IC50 = 1.2 μM; 50 μM SAM, 100 μM NCA) that reduces 3T3-L1 lipogenesis (EC50 = 30μM) and adipocytes 1-methylnicotinamide level (EC50 = 2.3 μM) without affecting related methyltransferases & enzymes in the NAD+ salvage pathway. 5-amino-1MQ shows in vivo therapeutic efficacy in murine models of DIO (20 mg/kg/d sc.), muscle injury (5 or 10 mg/kg bid. sc.), and intraperitoneal HeyA8 ovarian cancer metastasis (20 mg/kg/d ip.) with no adverse effects to the animals (up to 60 mg/kg/d). Note:1.89 mg iodide salt contains 1 mg eq of 5-amino-1MQ.
Substrate site-targeting, selective nicotinamide N-methyltransferase (NNMT) inhibitor with in vitro and in vivo efficay.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000102365
0000102634
0000097712

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Harshini Neelakantan et al.
Journal of medicinal chemistry, 60(12), 5015-5028 (2017-05-27)
Nicotinamide N-methyltransferase (NNMT) is a fundamental cytosolic biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small molecule inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure-activity relationships (SARs) for NNMT inhibitors.
Mark A Eckert et al.
Nature, 569(7758), 723-728 (2019-05-03)
High-grade serous carcinoma has a poor prognosis, owing primarily to its early dissemination throughout the abdominal cavity. Genomic and proteomic approaches have provided snapshots of the proteogenomics of ovarian cancer1,2, but a systematic examination of both the tumour and stromal
Harshini Neelakantan et al.
Biochemical pharmacology, 147, 141-152 (2017-11-21)
There is a critical need for new mechanism-of-action drugs that reduce the burden of obesity and associated chronic metabolic comorbidities. A potentially novel target to treat obesity and type 2 diabetes is nicotinamide-N-methyltransferase (NNMT), a cytosolic enzyme with newly identified
Harshini Neelakantan et al.
Biochemical pharmacology, 163, 481-492 (2019-02-13)
Aging is accompanied by progressive declines in skeletal muscle mass and strength and impaired regenerative capacity, predisposing older adults to debilitating age-related muscle deteriorations and severe morbidity. Muscle stem cells (muSCs) that proliferate, differentiate to fusion-competent myoblasts, and facilitate muscle

Questions

1–2 of 2 Questions  

  1. Can there be a chloride salt version that is white?

    1 answer

    1. Unfortunately, the iodide form of this compound is the only product option available at this time.

      Helpful?

  2. Does 5 amino 1MQ have iodine in it? 

    1 answer

    1. Yes, iodine is present as this product is the iodide salt of 5-Amino-1MQ . This is not a covalent bond and the Iodine will ionize in solution. Please see the link below to review a sample Certificate of Analysis:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/SML2832-5MG0000102634.pdf

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