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SML3490

Sigma-Aldrich

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
MDL number:
MFCD07995053
UNSPSC Code:
41106300
NACRES:
NA.77

Quality Level

100

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

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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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