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1-Propanaminium,2-(acetyloxy)-3-carboxy-N,N,N-trimethyl-, chloride (1:1), (2R)-(CAS No. 5080-50-2)

1-Propanaminium,2-(acetyloxy)-3-carboxy-N,N,N-trimethyl-, chloride (1:1), (2R)- C9H17NO4.HCl (cas 5080-50-2) Molecular Structure

5080-50-2 Structure

Identification and Related Records

【Name】
1-Propanaminium,2-(acetyloxy)-3-carboxy-N,N,N-trimethyl-, chloride (1:1), (2R)-
【Iupac name】
(3R)-3-acetyloxy-4-(trimethylazaniumyl)butanoate hydrochloride
【CAS Registry number】
5080-50-2
【Synonyms】
1-Propanaminium,2-(acetyloxy)-3-carboxy-N,N,N-trimethyl-, chloride, (2R)- (9CI)
1-Propanaminium, 2-(acetyloxy)-3-carboxy-N,N,N-trimethyl-, chloride, (R)-
Ammonium, (3-carboxy-2-hydroxypropyl)trimethyl-, chloride, acetate, (-)- (8CI)
Acetyl L-carnitine hydrochloride
Acetylcarnitine chloride
Branigen
L-Acetylcarnitine chloride
Levacecarnine hydrochloride
Normobren
O-Acetylcarnitine hydrochloride
ST 200
Zibren
l-Acetylcarnitinehydrochloride
【Molecular Formula】
C9H17NO4.HCl (Products with the same molecular formula)
【Molecular Weight】
239.7
【Inchi】
InChI=1/C9H17NO4.ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;/h8H,5-6H2,1-4H3;1H
【Canonical SMILES】
CC(=O)OC(CC(=O)[O-])C[N+](C)(C)C.Cl
【Isomers smiles】
CC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C.Cl
【MOL File】
5080-50-2.mol

Chemical and Physical Properties

【Appearance】
white powder
【Density】
g/cm3
【Melting Point】
194℃
【Boiling Point】
°Cat760mmHg
【Refractive Index】
-28 ° (C=1, H2O)
【Flash Point】
°C
【Alpha】
-29 o (C=1, H2O)
【Water】
soluble
【Solubilities】
H2O: 100 mg/mL
【Color/Form】
white
【Storage temp】
2-8°C
【Computed Properties】
Molecular Weight:239.69652 [g/mol]
Molecular Formula:C9H18ClNO4
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:5
Exact Mass:239.092436
MonoIsotopic Mass:239.092436
Topological Polar Surface Area:66.4
Heavy Atom Count:15
Formal Charge:0
Complexity:214
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Transport】
OTH
【Formulations/Preparations】
Juvenon: acetyl-L-carnitine and alpha lipoic acid
【Exposure Standards and Regulations】
Since 1994, dietary supplements have been regulated under the Dietary Supplement Health and Education Act (DSHEA). The DSHEA requires no proof of safety for dietary supplements on the market prior to October 15, 1994. Labeling requirements for such supplements allow warnings and dosage recommendations as well as substantiated "structure or function" claims. All claims must prominently note that they have not been evaluated by the FDA, and they must bear the statement "This product is not intended to diagnose, treat, cure, or prevent any disease".
【Specification】

The Acetyl-L-Carnitine Hydrochloride with the cas number 5080-50-2, is also called (1)Acetylcarnitine L-form HCl ; (2)1-Propanaminium, 2-(acetyloxy)-3-carboxy-N,N,N-trimethyl-, chloride, (R)- . It belongs to the following product categories: (1)L-Carnitine Series; (2)Chiral Compound; (3)Lipid signaling and so on.

Propertes of Acetyl-L-Carnitine Hydrochloride: (1)ACD/LogP: -4.15 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -3.55 ; (4)ACD/LogD (pH 7.4): -3.55 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 1 ; (8)ACD/KOC (pH 7.4): 1 ; (9)#H bond acceptors: 5 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 6 ; (12)Polar Surface Area: 52.6??2

Acetyl-L-Carnitine Hydrochloride seem to be crystallline powder. It is an important dietary supplement. Studies shows Acetyl-L-Carnitine Hydrochloride, which is a natural substance, present in the human body, especially in muscles, in the brain, and in the male testicles. ALC is the acetylated, high-energy form of L-Carnitine. Acetyl-L-Carnitine Hydrochloride is quite irritating to eyes, respiratory system and skin. Hence, when you are using it, please wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And Acetyl-L-Carnitine Hydrochloride should be stored at 2-8°C to protect from losing effectiveness.

You can still convert the following datas into molecular structure :
1. SMILES: [Cl-].O=C(O[C@@H](C[N+](C)(C)C)CC(=O)O)C
2. InChI: InChI=1/C9H17NO4.ClH/c1-7(11)14-8(5-9(12)13)6-10(2,3)4;/h8H,5-6H2,1-4H3;1H/t8-;/m1./s1

【Octanol/Water Partition Coefficient】
log Kow = -4.62 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... Acetylation of L-carnitine.
Preparation from carnitine extracted from meat.
【Usage】

Acetyl-L-Carnitine (ALC) is an important dietary supplement. ALC is a natural substance, present in the human body, especially in muscles, in the brain, and in the male testicles. ALC is the acetylated, high-energy form of L-Carnitine.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. While no potent nootropic drugs have yet been accepted for general use, several are being actively investigated.
- A group of water-soluble vitamins, some of which are COENZYMES.
【Therapeutic Uses】
L-Carnitine, acetyl-L-carnitine, and/or propionyl-L-carnitine may be used for replacement therapy to restore normal carnitine concn and/or a normal nonesterified-to-esterified carnitine ratio ...
/EXPL THER/ ... A recent meta-analysis of 21 double-blind clinical trials of ALC in the treatment of mild cognitive impairment and mild Alzheimer's disease showed significant efficacy vs. placebo. A meta-analysis of 4 clinical trials of LA for treatment of neuropathic deficits in diabetes showed significant efficacy vs. placebo. [Ames BN, Liu J; Ann N Y Acad Sci 1033: 108-16 (2004)]
【Biomedical Effects and Toxicity】
In mammals, the carnitine pool consists of nonesterified L-carnitine and many acylcarnitine esters. Of these esters, acetyl-L-carnitine is quantitatively and functionally the most significant. Carnitine homeostasis is maintained by absorption from diet, a modest rate of synthesis, and efficient renal reabsorption. Dietary L-carnitine is absorbed by active and passive transfer across enterocyte membranes. Bioavailability of dietary L-carnitine is 54-87% and is dependent on the amount of L-carnitine in the meal. Absorption of L-carnitine dietary supplements (0.5-6 g) is primarily passive; bioavailability is 14-18% of dose. Unabsorbed L-carnitine is mostly degraded by microorganisms in the large intestine. Circulating L-carnitine is distributed to two kinetically defined compartments: one large and slow-turnover (presumably muscle), and another relatively small and rapid-turnover (presumably liver, kidney, and other tissues). At normal dietary L-carnitine intake, whole-body turnover time in humans is 38-119 h. In vitro experiments suggest that acetyl-L-carnitine is partially hydrolyzed in enterocytes during absorption. In vivo, circulating acetyl-L-carnitine concentration was increased 43% after oral acetyl-L-carnitine supplements of 2 g/day, indicating that acetyl-L-carnitine is absorbed at least partially without hydrolysis. After single-dose intravenous administration (0.5 g), acetyl-L-carnitine is rapidly, but not completely hydrolyzed, and acetyl-L-carnitine and L-carnitine concentrations return to baseline within 12 h. At normal circulating l-carnitine concentrations, renal l-carnitine reabsorption is highly efficient (90-99% of filtered load; clearance, 1-3 mL/min), but displays saturation kinetics. Thus, as circulating L-carnitine concentration increases (as after high-dose intravenous or oral administration of L-carnitine), efficiency of reabsorption decreases and clearance increases, resulting in rapid decline of circulating L-carnitine concentration to baseline. Elimination kinetics for acetyl-L-carnitine are similar to those for L-carnitine. There is evidence for renal tubular secretion of both L-carnitine and acetyl-L-carnitine. Future research should address the correlation of supplement dosage, changes and maintenance of tissue L-carnitine and acetyl-L-carnitine concentrations, and metabolic and functional changes and outcomes. [Rebouche CJ; Ann N Y Acad Sci 1033: 30-41 (2004)] PubMed Abstract
Acetyl-L-carnitine (ALC), a physiological component of the L-carnitine family, has been proposed for treating Alzheimer's disease in pharmacological doses. As this condition requires prolonged therapy, its kinetics has been examined after a multiple dose regimen, involving different routes of administration, in 11 patients suffering from Senile Dementia of Alzheimer Type. The study design comprised a 3-day basal observation period, sham treatment with repeated blood sampling; treatment with 30 mg/kg iv [corrected] for 10 days (plasma kinetics was studied on the 7th day), and 50 days of 1.5 g/day [corrected] po given in three daily doses. Total acid soluble L-carnitine, L-carnitine and acetyl-L-carnitine in plasma and CSF were evaluated using an enantioselective radioenzyme assay. Short chain L-carnitine esters were calculated as the difference between total and free-L-carnitine. The plasma concentrations of individual components of the L-carnitine family did not change during the three days of the basal period, nor were they affected during the sham therapy period. Following the iv.bolus injections, the plasma concentrations showed a biphasic curve, with average t1/2 of 0.073 hr and 1.73 hr, respectively. At the end of oral treatment, plasma acetyl-L-carnitine and L-carnitine short chain esters were significantly higher than during the run-in phase. The CSF concentrations paralleled those in plasma, suggesting that ALC easily crosses the blood-brain barrier. ... [Parnetti L et al; Eur J Clin Pharmacol 42 (1): 89-93 (1992). Erratum in: Eur J Clin Pharmacol 44 (6): 604 (1993)] PubMed Abstract
The pharmacokinetics of acetyl-L-carnitine hydrochloride were investigated in 6 healthy volunteers of both sexes after iv injection of 500 mg of the drug, expressed as inner salt. Plasma concentrations and urinary excretion of acetyl-L-carnitine (A), L-carnitine (B) and total acid soluble L-carnitine fraction were evaluated over a period lasting from 24 h before to 48 h after the administration. Plasma concentrations of A increased quickly after administration and then declined reaching base values within 12 h. Conversely, plasma concentrations of B rose more slowly, reaching a peak in 30-60 min, and then declined to base values within 24 h. Most of the injected dose of acetyl-L-carnitine was recovered in the urine during the first 24 h after administration as B and A. Mean renal clearance of both A and B during the first 12 h after injection was higher than the base values, suggesting the presence of a saturable tubular reabsorption process which may counterbalance major changes occurring in plasma concentrations of L-carnitine pattern. /Acetyl-L-carnitine hydrochloride/ [Marzo A et al; Eur J Clin Pharmacol 37 (1): 59-63 (1989)] PubMed Abstract
L-carnitine and its short-, medium- and long-chain acyl esters constitute the L-carnitine family. These compounds in the body are equilibrated according to a homeostatic equilibrium preserved and, when impaired, restored by a dynamic inter-exchange between L-carnitine and its esters, catalysed by carnitine acyl transferases, and a tubular reabsorption process with differentiated thresholds for each component. The interaction of these compounds with albumin and plasma proteins of rats, dogs and humans was carefully investigated by means of ultrafiltration and gel filtration techniques. Results obtained demonstrate that L-carnitine and its short-chain esters, namely acetyl-L-carnitine and propionyl-L-carnitine, do not interact with either albumin or plasma proteins; octanoyl-L-carnitine interacts in a measurable even if poor extent (12-30%), whereas palmitoyl-L-carnitine, a molecule with a detergent activity, is completely bound to albumin and plasma proteins. PMID: [Marzo A et al; Eur J Drug Metab Pharmacokinet Spec No 3:364-8 (1991)] PubMed Abstract
... Acetyl-L-carnitine ... is better absorbed from the small intestine than L-carnitine and more efficiently crosses the blood-brain barrier (ie, gets into brain tissue).
L-carnitine and acetyl-L-carnitine (ALC) are administered orally or intravenously and are then absorbed in the jejunum by simple diffusion. Transport into cellular tissue is via an active transport mechanism, with studies showing plasma concentrations of ALC and L-carnitine reaching an equilibrium via carnitine acetyl-transferase activity. Both iv and oral administration result in a corresponding increase in cerebrospinal fluid (CSF) concentrations of ALC, indicating it readily crosses the blood-brain barrier. L-carnitine and its esters undergo little metabolism and are subsequently excreted in the urine via renal tubular reabsorption. The rate of clearance increases with the plasma concentration of these substances.
L-Carnitine and acylcarnitine esters are present in all tissues. In most tissues and cells, they are present in higher concn than in the circulation ... L-carnitine and acetyl-L-carnitine are concn in most tissues via the high-affinity, Na+-dependent organic cation transporter OCTN2 ... OCTN2 binds acetyl-L-carnitine and propionyl-L-carnitine with comparable affinity. This protein is highly expressed in heart, placenta, skeletal muscle, kidney, pancreas, testis, and epididymis and weakly expressed in brain, lung, and liver ...
... At a filtered load of 50 umol/L, the efficiency of L-carnitine and acylcarnitine ester reabsorption is 90 to 98% /in kidneys/. However, as the filtered load of L-carnitine incr, as, eg after consumption of a dietary supplement or after iv infusion, the efficiency of reabsorption declines rapidly ... Clearance of acylcarnitine esters is often higher than that of nonesterified L-carnitine /in kidneys/. Experimental studies have shown that in rats and humans, kidneys are able to synthesize acetyl-L-carnitine from L-carnitine and either acetoacetate or beta-hydroxybutyrate, and that L-carnitine, acetyl-L-carnitine, and gamma-butyrobetaine (also synthesized in human kidneys) are secreted from mucosal cells into tubular lumen. Because the kinetics of transport of these metabolites by the sodium-dependent L-carnitine transporter are not different, the relative proportions appearing in urine reflect not only those in the glomerular filtrate, but also those in the renal tubular epithelium that are secreted into the lumen. Thus, under conditions of rapid intracellular synthesis of acylcarnitine esters or direct accumulation from the circulation, secretion of these species will lead to a higher proportion of acylcarnitine esters in urine compared to that in the circulation ... Kidneys may be substantially involved in the regulation of circulating acylcarnitine ester concn.

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