BLIVGR KAMM.
I030
would have all of the propertes found in the experimental work. Such a mixture might reasonably be expected to be formed in petroleum production. CLBVBLAND, OHIO. I
[CONTRIRWTION FROM THE CHEMICAL AND FROM THE
LABORATORY OF
THE UNIVERSITY OF ILLINOIS
ABBOTTLABORATORIES, OF CRICAGO, ILLINOIS. 1
THE RELATIONSHIP BETWEEN CHEMICAL CO NSTITUTIOM AND PHYSIOLOGICAL ACTION IN LOCAL ANESTHETICS. I. HOMOLOGS OF PROCAINE. BY OLIVER KAMM. Received February 23, 1920.
Several simple homologs of the well-known anesthetic, procaine (Formula I),I have been described in the literature. The formulas for compounds of this type which differ from the parent substance in that they possess one more carbon atom are represented structurally as follows : NHz (pare)
NH2 (para)
/
/
\/
GH4
C--O-CH~-CH~-N (1).
(:I
CBH~
,;"" (para)
c6&\
//O
CH~-C-O-CHa--CH~----N (111).
\/?
H C--O--C--C€I~-N
I
(11).
/CzHa
\en%
CHp
(::
Compound I1 is described in the German patent literature,2 but the writer is not aware of published data recording the physiological action of this individual. Compound 111 has been synthesized more recently by Pyman3 and has been found to be inactive as an anesthetic. It is to be noted that the latter compound is an amino-alcohol ester of an aliphatic acid (9-aminophenyl acetic acid) whereas a maximum anesthetic &ect appears to develop when the carbonyl group is united directly t o the aromatic nucleus. Such a type of linkage is, however, not essential, provided that the carbonyl group of the ester be united to an unsaturated carbon atom,* such as is illustrated by Formulas IV and V. B o t h of these Procaine (also called novocaine) is the mono1 This is the formula of the free base. hydrochloride of this compound. 2 Friedlaender, 8, 995;D. R. P. 179,627. 8 J. Chem. Soc., 111, 167, 1119 (1917). 4 For exceptions see Fourneau, J. pharm. chinz., 171 2, 337, 397 (1910).
IIOMOLOGS OR PROCAINE.
1031
compounds have been prepared’ and found to possess anesthetic properties.
No
/CZIi6
-CH =CH-C-0-CHz-4Hr-N (IV).
HnN-
‘C2Ha 0
Q
H H / /
CzHs
--C =C--C--O--CH~-CH~-CH~--N
04.
