461-06-3 Usage
Originator
Flatistine,Sauba,France,1978
Uses
antihyperlipoproteinemic, gastric/ pancreatic secretion stimulant
Manufacturing Process
9.3 g of epichlorohydrin was added at a temperature of 40°-50°C under
stirring to 9.6 g of trimethylamine hydrochloride dissolved in 10 cc of water.
Continuing the reaction for an hour at the above temperature, the reaction
product was concentrated under reduced pressure to obtain the crystals of 3-
chloro-2-oxypropyl trimethyl ammonium chloride which were recrystallized
with 25 cc of ethanol. The crystals obtained by concentrating the mother
liquor were also recrystallized. The yield was 17.4 g (MP 190°C, yield 91.5%).
This substance occurs as white, somewhat hygroscopic crystals and is readily
soluble in water or alcohol, but insoluble in benzene, toluene, ether, acetone
or chloroform.The result of analysis assuming (C6H15C10N)+Cl--calculated value: N, 7.45%;
total Cl, 37.7%; Cl-, 18.88%. Observed value: N, 7.36%; total Cl, 37.54%;
Cl-, 18.98%.18.8 g of 3-chloro-2-oxypropyl trimethyl ammonium chloride was dissolved in
a mixed solvent composed of 19 cc of methanol and 1 cc of water. 5.1 g of
sodium cyanide dissolved in 8 cc of water was dropped into the solution at
50°C under stirring. After dropping, the mixture was held at this temperature
for 30 minutes under stirring. The reaction product was then neutralized with
6 N hydrochloric acid toward pH 5, and, after cooling, sodium chloride
separated out and was filtered. The filtrate was concentrated to dryness under
reduced pressure, and the residue was washed with small quantity of ethanol.
Drying the residue, dissolving in hot methanol, filtering off insoluble matters,
and cooling mother liquor, the crystals of 3-cyano-2-axypropyl trimethyl
ammonium chloride which deposited out were filtered and dried. Yield 16.7 g
[MP (decomposition) 220°-223°C, yield 93.4%].12.5 cc of concentrated hydrochloric acid was added to 17.9 g of 3-cyano-2-
oxypropyl trimethyl ammonium chloride. Gradually heating the mixture on a
water bath under stirring, so bringing the temperature up to 98°C at the end
of about 3 hours, 9 cc of water was added. After cooling, free hydrochloric
acid was neutralized with 3 cc of 6 N sodium hydroxide, and then by adding 1
g of active charcoal, the reaction product was decolorized and filtered. The
filtrate was concentrated to almost dryness under reduced pressure. Then,
this concentrate was, after washing with 10 cc of ethanol, dried. Yield 24.7 g.The dried product was dissolved in 46.5 cc of glacial acetic acid by heating on
a boiling water bath. The insoluble matter is removed by filtering hot, and on
cooling the mother liquor, crystals of carnitine hydrochloride separated out.
The crystals were filtered, washed with 10 cc of ethanol, and dried.
Recrystallizing 19.7 g of the crude carnitine with methanol, 17 g of the refined
carnitine was obtained [MP 195°-198°C (decomposing point), yield 86%], The
overall yield of the refined carnitine through whole steps was about 74%.
Carnitine thus prepared was an odorless, white, crystalline powder, having a
strong acid taste.
Therapeutic Function
Gastric stimulator, Pancreatic stimulator
Purification Methods
The S(L) isomer is levocarnitine, Vitamin B7. The R or S isomers crystallise from EtOH/Me2CO (hygroscopic). The R or S hydrochlorides crystallise from hot EtOH or EtOH/Et2O and have m 142o(dec). The RS-isomer crystallises from hot EtOH (hygroscopic). The RS hydrochloride crystallises in needles from hot EtOH and has m 196o(dec). [(±) Mazzetti & Lemmon J Org Chem 22 228 1957, Beilstein 4 H 513, 4 I 548, 4 II 937-8, 4 III 1632-5, 4 IV 3185.]
Check Digit Verification of cas no
The CAS Registry Mumber 461-06-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 461-06:
(5*4)+(4*6)+(3*1)+(2*0)+(1*6)=53
53 % 10 = 3
So 461-06-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H15NO3/c1-8(2,3)5-6(9)4-7(10)11/h6,9H,4-5H2,1-3H3
461-06-3Relevant articles and documents
PROCESS FOR THE PRODUCTION OF CARNITINE BY CYCLOADDITION
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Page/Page column 10, (2012/02/03)
The invention relates to a method for the production of L-carnitine, wherein a chiral β-lactone carnitine precursor is obtained by a [2+2] cycloaddition of ketene with an aldehyde X—CH2—CHO, wherein X is selected from Cl, Br, I and trimethylamine, in the presence of a chiral catalyst.
CARNITINE CONJUGATES AS DUAL PRODRUGS, METHODS OF PRODUCTION AND USES THEREOF
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Page/Page column 29, (2010/11/30)
The present invention discloses novel dual prodrug compounds of formula (1), methods for their preparation and intermediates in their syntheses, formula (1): wherein A is a single bond, -0-, or -CH2-; m and n vary independently and are an integer from 1 to 15; p and q vary from 0 to an integer from 1 to 4; B is a single bond or -CR3R4; D is formula (2): or formula (3): and X is halogen; R1 to R4 are various substituents selected to optimize the physiochemical and biological properties such as, lipophilicity, bioavailability, and pharmacokinetics of compounds of Formula 1; and R1 and R2 or R3 and R4 may optionally be tethered together to form a 3- to 7-membered alicyclic ring. These compounds are useful for the treatment of various infections, metabolic, cardiovascular and neurological disorders.
Stabilization of polynucleotide complexes
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Page 7, (2008/06/13)
Polynucleotide complexes are stabilized by adding a cryoprotectant compound and lyophilizing the resulting formulation. The lyophilized formulations are milled or sieved into a dry powder formulation which may be used to deliver the polynucleotide complex. Delivery of the polynucleotide to a desired cell tissue is accomplished by contacting the tissue with the powder to rehydrate it. In a preferred embodiment, a dry powder formulation is used to induce genetic modification of a patient's lung tissue.