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2504-11-2

2504-11-2 Structure

2504-11-2 Structure
IdentificationMore
[Name]

ACETYL-DL-CARNITINE HYDROCHLORIDE
[CAS]

2504-11-2
[Synonyms]

TIMTEC-BB SBB003214
Acetyl-DL-carnitineHCl
acetyldl-carnitinechloride
d,l-acetylcarnitin-chlorid
(+/-)-ACETYLCARNITINE CHLORIDE
ACETYL-DL-CARNITINE HYDROCHLORIDE
acetyl-dl-carnitine hcl crystalline
Acetyl-DL-carnitinehydrochloridecrystalline
(RS)-3-Acetoxy-4-(trimetylammino)butyrate hydrochloride
(±)-(2-acetoxy-3-carboxypropyl)trimethylammonium chloride
(+/-)-3-ACETOXY-4-(TRIMETHYLAMMONIO)BUTYRATE HYDROCHLORIDE
[+/-]-3-ACETOXY-4-(TRIMETHYLAMMONIO)BUTYRATE HYDROCHLORIDE
(2-acetyloxy-4-hydroxy-4-oxobutyl)-trimethylazanium chloride
(2-acetoxy-4-hydroxy-4-keto-butyl)-trimethyl-ammonium chloride
(2-acetyloxy-4-hydroxy-4-oxo-butyl)-trimethyl-azanium chloride
(+-)-(3-carboxy-2-hydroxypropyl)trimethylammoniumchlorideacetate
(3-carboxy-2-hydroxypropyl)trimethyl-,chloride,acetate,(+-)-ammoniu
2-(acetyloxy)-3-carboxy-n,n,n-trimethyl-,chloride,(+-)-1-propanaminiu
[EINECS(EC#)]

219-709-3
[Molecular Formula]

C9H18ClNO4
[MDL Number]

MFCD00080826
[Molecular Weight]

239.7
[MOL File]

2504-11-2.mol
Chemical PropertiesBack Directory
[Melting point ]

181 - 183°C
[storage temp. ]

−20°C
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Slightly)
[form ]

Solid
[color ]

White to Off-White
[Water Solubility ]

Soluble to 100 mM in water
[Stability:]

Hygroscopic
[CAS DataBase Reference]

2504-11-2(CAS DataBase Reference)
Safety DataBack Directory
[WGK Germany ]

3
[RTECS ]

BP2979200
Hazard InformationBack Directory
[Uses]

(±)-Acetylcarnitine Chloride is a drug absorption-enhancing agent in the gastrointestinal tract.
[Biological Activity]

(±)-acetylcarnitine chloride is an agonist for cholinergic.acetylcholine receptor (achr) is an integral membrane protein receptor for acetylcholine. there are two kinds of achrs: nicotinic acetylcholine receptors and muscarinic acetylcholine receptors.(±)-acetylcarnitine chloride is a cholinergic agonist and an intermediate in lipid metabolism [1]. in retinal ganglion cells, acetylcarnitine and acetylcholine inhibited gabaergic responses to exogenous gaba and gabaergic inhibitory postsynaptic currents [2].in dogs with coronary ligation, (-)-carnitine chloride (lcc) (300 mg/kg) and acetyl (-)-carnitine chloride (alcc) (300 mg/kg) inhibited the ventricular arrhythmia. also, lcc and alcc improved oxidative phosphorylation rate and the mitochondrial function [1]. in the mouse hot plate test, acetyl-l-carnitine (alcar) (100 mg/kg) exhibited analgesia. while, u-73122 and neomycin (the phospholipase c (plc) inhibitors) blocked the increase of the pain threshold induced by alcar. licl that impairing phosphatidylinositol synthesis antagonized the antinociception in a dose-dependent way. pma and pdbu (pkc activators) blocked the increase of the pain threshold in a dose-dependent way. these results suggested that alcar analgesia required the participation of the plc-ip3 pathway [3].
[Biochem/physiol Actions]

Weak cholinergic receptor agonist; intermediate in lipid metabolism.
[in vivo]

In rats, the infusion of 2 mg (±)-Acetylcarnitine chloride decreases blood flow through the hind limb vasculature 50%. (±)-Acetylcarnitine chloride also potentiates the inhibitory effect of adrenaline on the isolated rabbit duodenum[3].

[Purification Methods]

Recrystallise the chloride from isopropanol. Dry it over P2O5 under high vacuum. The S-betaine crystallises from EtOH/Et2O with m 145o(dec) and is hygroscopic; it has [] D -19.5o (c 6, H2O). [Krimberg & Wittandt Biochem Z 251 231 1932, Strack et al. Z Physiol Chem 238 191 1936, Beilstein 4 III 1630, 1632.]
[References]

[1]. imai s, matsui k, nakazawa m, et al. anti-arrhythmic effects of (-)-carnitine chloride and its acetyl analogue on canine late ventricular arrhythmia induced by ligation of the coronary artery as related to improvement of mitochondrial function. br j pharmacol, 1984, 82(2): 533-542.
[2]. b?hring r, standhardt h, martelli ea, et al. gaba-activated chloride currents of postnatal mouse retinal ganglion cells are blocked by acetylcholine and acetylcarnitine: how specific are ion channels in immature neurons? eur j neurosci, 1994, 6(7): 1089-1099.
[3]. galeotti n, bartolini a, calvani m, et al. acetyl-l-carnitine requires phospholipase c-ip3 pathway activation to induce antinociception. neuropharmacology, 2004, 47(2): 286-294.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

2504-11-2(sigmaaldrich)
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