(SANITIZED)UNCLASSIFIED POLISH PAPER ON THE TRANSFORMATION OF DIALLYLBARBITURIC ACID INTO HYDROXYPROPY ACID(SANITIZED)

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP80T00246A014900220001-2
• Release Decision: RIPPUB
• Original Classification: C
• Document Page Count: 4
• Document Creation Date: December 22, 2016
• Document Release Date: December 13, 2011
• Sequence Number: 1
• Publication Date: August 15, 1961
• Content Type: REPORT

Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246AO14900220001-2
Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246AO14900220001-2
 Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246AO14900220001-2
FOR OFFICIAL USE ONLY
August 15, 1961
60
RRCVIT RRBZARM OF PROP 8OR BO8RAI1
11IIXI AM) COM B
An interesting part of Bobraifskir research has been the transforiation of 5,5-
diallylbarbituric acid into 5-al]y1-5-(P-hydroVpropprl)-Urbituric acid (I). frith
this operation, the hypnotic activity was almost eytainated while a sort of
long.laeting tranquilizing effect remained (in man, hardly in aniasls).4'5-9ej7
The modification of pharmacodynamic activity realized by chemical means has been
considered to be the consequence of the introduction of the hydroxy group into the
molecule of diallylbarbituric acid. In order to obtain additional data illustrating
the pharmacodynamic role of the bydroxy group in compound. I, three esters of it
were now prepared and their activities determined: the 5,4,5-trimetboxpr benzoic
ester, the p-nitrobenzoic ester, and the p-aminobenzoic ester. They showed,
however, no distinct pharmacological activities at all. This seems to agree with
the theore that the hydroxy group is necessary to'obt&in the type of activity
shown by I.
FOR OFFICIAL USE ONLY
.
Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80TOO246AO14900220001-2
 Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246A014900220001-2
Full urtlu,?
---co"',
IQi--CO cHZ-(MOH 3
(I)
The 3,4,5-trimethorbenzoic ester of I melts at 201-201.5?C; the p-nitrobenzoic
ester of I has a dp of 2.15-217?C; the p-ami.nobenzoic ester of I melts at 183?C.
Hano and Wojevddski' (Dept. of Pharmac., Med. Acad., WrocLav) studied the
pharmacological action of three polyphenyl derivatives of aminopropane:9
1,3-Biphenyl-2-amino-propane (B10) (II)
1,1-Biphenyl-2-amino-propane (B11) (III)
1,1,3-triphenyl-2-amino-propane (B12) (IV)
~~_.Qi4-CEi-CH
LH2 .HC1
r s
Cl
Tyro of these substances (compounds Blo and B11) or II and III, have been ph&rxaco-
logically tested before in part while compound B12 or III was first synthesized
and tested by Bobrarfaki and Jac6biec (ink s, 1961).
All three compounds are more toxic than 'Benzedrine'-SR&F (050 of 'Benzedrine
200 mg,k ., LDao,of B1 or II is 160 mg,kg.; I.D50 of B11 or III is 64 mg,kg.; Ixso
of B12 or IV 1& 12 mg.7]Sg., animal species and route of administration unrevealed
in English a$sttact at our disposal).9
FOR OFFICIAL USE ONLY
Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246A014900220001-2
 Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246AO14900220001-2
FOR OFFICIAL USE ONLY
-3-
All three compounds exert a stimulating action on the CNS; they stimulate
greatly the respiratory rate, increase the spontaneous or reflex sensibility
of animals, cause violent convulsions, and suppress the depressant action of
morphine on the respiratory center. Their influence on circulation in tocto
1s sudo m to that of 'Benzedrine'-SX&F. Arterial pressure curves show one or
two phases, depending on the dose administered; small doses (to 1 mg/kg.) induce
occurrence of one phase, enhancing arterial pressure while moderate doses
(1-5 mg/kg.) produce a biphasic effect; a short-lasting hypotensive action
.is followed by a long-lasting decrease in the blood pressure. Atropine
suppresses or reduces the hypotensive phase without affecting the hypertensive
phase. The opposite is true for regitine.s
Cardioplethysmographic studies on the isolated rabbit and frog heart show a deteriorating
effect on the heart muscle (bradycardia in spite of atropinization), marked
increase in the heart volume and reduction of the systolic-diastolic amplitude.
The Polish workers conclude that the introduction of additional phenyl rings into
the phenylisopropylamine molecule produces a marked increase in toxicity while,
otherwise,,the in properties of the parent compound, 'Benzedrine'-SW are not
affected.
References
2.
3-
4. Bobrariski, B., Jako'biec, T., and Prelicz, D., Roczniki Chemie 30:175(1956).
5. Kapudciriski, W., Gamski, M., and Krudysz, J., Pami?tnik XVI Zjazdu Polskiego
Taw. Okulistycznego, Szczecin, 1958, p. 383.
6. Wilimowski, M., Gieldamawski, J., and Kpdzierska, L., Archie. Immt'nol. i.Terap.
Doiw. 7:95(1959)-
7- Wilimowski, M., Orzechowska, K., and ICgdzierska, L., ibidem. 6:749(1958).
8. Bobratiski, B., Gieldanowski, J., K dzierska, L., and Tumanowicz., A.,
Archiv. I maunol. i. Terap. Dodv. 9fNo.1):1-6(1961).
9. Hano., J., and WoJewodzki, W., Archie. Immunol. i. 'Fjsrap. Dodw. 9:7-24(1961).
Declassified in Part - Sanitized Copy Approved for Release 2011/12/13: CIA-RDP80T00246AO14900220001-2