17692-39-6 Usage
Originator
Erbocain,Heilit,W. Germany,1967
Manufacturing Process
64 parts of dry sodium phenolate are dissolved in 300 parts of methylisobutyl
ketone by heating at 110°C. 103 parts of γ-(4-chloromethylphenyl)propyl
chloride are added dropwise with agitation, and the mixture is maintained at
110°C for a period of 4 hours with constant agitation. After cooling, the
reaction mixture is washed 2 or 3 times with 100 parts of water and the
methylisobutyl ketone is distilled off under reduced pressure. The residue is
taken up in 200 parts of petroleum ether and γ-(4-phenoxymethylphenyl)
propyl chloride is crystallized by addition of ice water. The crystals are filtered
off employing a suction pump and dried at 100°C in vacuo (10 mm Hg) for 1
to 2 hours. The γ-(4-phenoxymethylphenyl)propyl chloride melts at 55°C to
56°C after recrystallization from petroleum ether.
130 parts of γ-(4-phenoxymethylphenyl)propyl chloride are heated under
reflux at 140°C for 24 hours with 130 parts of morpholine. The reaction
mixture is treated to give N-[(γ-phenoxymethylphenyl)propyl]-morpholine,
which forms colorless crystals melting at 52°C to 53°C when crystallized from
n-heptane.
Therapeutic Function
Local anesthetic
Safety Profile
Poison by intravenous and intraperitoneal routes. Moderately toxic by subcutaneous route. When heated to decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 17692-39-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,6,9 and 2 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 17692-39:
(7*1)+(6*7)+(5*6)+(4*9)+(3*2)+(2*3)+(1*9)=136
136 % 10 = 6
So 17692-39-6 is a valid CAS Registry Number.
InChI:InChI=1/C20H25NO2/c1-2-6-20(7-3-1)23-17-19-10-8-18(9-11-19)5-4-12-21-13-15-22-16-14-21/h1-3,6-11H,4-5,12-17H2
17692-39-6Relevant academic research and scientific papers
Metabolism of the local anaesthetic fomocaine by rat liver mitochondria
Blume,Oelschlaeger
, p. 1731 - 1735 (2007/10/02)
Fomocaine (Erbocain) is metabolized by different routes in rat and beagle. By highly purified rat liver mitochondria it was metabolized to its N-oxide only. The N-oxide was reduced to fomocaine by a reductase localised in the matrix or in the inner membrane of the mitochondria. C-Hydroxylation with subsequent conjugation reactions as well as oxidative N- or O-dealkylation found in intact animals were not observed in mitochondria.
On a novel fomocaine synthesis: 10th communication: on synthesis of new compounds with local anaesthetic activity
Oelschlaeger,Iglesias-Meier,Goetze,Schatton
, p. 1625 - 1628 (2007/10/05)
4 [3 (4 Phenoxymethyl phenyl) propyl] morphine (fomocaine, Erbocain) is a very active topical local anesthetic with low toxicity. A new synthesis starting from 4-phenoxy-methyl-benzonitrile, via a modified Willgerodt-Kindler reaction, is reported. The yield is of the same order as with the known technical process starting from 3-phenylpropanol. The distinct advantage of the new procedure is the avoidance of the C-chloromethylation of 3-phenylpropylchloride during which process the o-chloromethyl derivative is also formed, and this cannot be separated by fractional distillation.
