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Merck
CN

SML3490

FMC

≥98% (HPLC)

Synonym(s):

Dimethyl(fluoromethyl)(2-hydroxyethyl)ammonium chloride, Fluorocholine chloride, Fluoromethylcholine chloride, N-(Fluoromethyl)-2-hydroxy-n,n-dimethylethanaminium chloride, NSC720948

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About This Item

Empirical Formula (Hill Notation):
C5H13FNO·Cl
CAS Number:
459424-38-5
Molecular Weight:
157.61
UNSPSC Code:
41106300
NACRES:
NA.77
MDL number:
MFCD07995053

Key Documents

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Product Name

FMC, ≥98% (HPLC)

SMILES string

FC[N+](CCO)(C)C.[Cl-]

InChI

1S/C5H13FNO.ClH/c1-7(2,5-6)3-4-8;/h8H,3-5H2,1-2H3;1H/q+1;/p-1

InChI key

QJEHIIJVWXGJAB-UHFFFAOYSA-M

assay

≥98% (HPLC)

form

(Crystals to semi-solid)

storage condition

under inert gas

color

colorless to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

100

Related Categories

Biochem/physiol Actions

FMC is a monofluorinated choline that acts as a nonlethal, mechanism-based irreversible inhibtor (pseudosubstrate-based suicide inhibitor) against gut anaerobic bacterial glycyl radical enzyme (GRE) cutC choline trimethylamine (TMA) lyase-catalyzed TMA production from choline (IC50 = 0.9 nM/P. mirabilis & 1.4 nM/D. alaskensis rec. CutC/D) without affecting the bacterial growth (P. mirabilis, E. fergusonii, and P. penneri). A single FMC oral dose (100 mg/kg) to mice on choline-supplemented diet significantly reduces plasma trimethylamine N-oxide (TMAO) level (up to 3 days) as well as diet-induced platelet responsiveness and thrombus formation without toxicity or increased bleeding risk.
Orally active gut bacterial choline trimethylamine (TMA) lyase cutC inhibtor with TMA- & TMA N-oxide (TMAO)-lowering efficacy in vitro and in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000469148
0000454989
0000454989
0000469148
0000463044

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Adam B Roberts et al.
Nature medicine, 24(9), 1407-1417 (2018-08-08)
Trimethylamine N-oxide (TMAO) is a gut microbiota-derived metabolite that enhances both platelet responsiveness and in vivo thrombosis potential in animal models, and TMAO plasma levels predict incident atherothrombotic event risks in human clinical studies. TMAO is formed by gut microbe-dependent

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