25090-18-0 Usage
Description
Piperovatine, an alkaloid with the empirical formula C16H21O2N, was first isolated from Piper ovatum and later found in Ottonia vehlii. It crystallizes from ethyl acetate (Et20) in colorless needles and exhibits a unique ultraviolet spectrum with a single broad absorption maximum at 262 millimicrons. Piperovatine features a trans configuration for both double bonds in its unsaturated side chain. It acts as a temporary depressant on motor and sensory nerve fibers, as well as sensory nerve endings. Additionally, it possesses properties of a heart poison and functions as a spinal cord stimulant in frogs, inducing a tonic spasm similar to that caused by strychnine.
Uses
Used in Pharmaceutical Applications:
Piperovatine is used as a therapeutic agent for its effects on the nervous system, particularly as a temporary depressant of motor and sensory nerve fibers and sensory nerve endings. Its ability to modulate nerve activity makes it a potential candidate for the treatment of various neurological disorders.
Used in Cardiovascular Applications:
Due to its heart poison properties, piperovatine can be utilized in the development of drugs targeting cardiovascular conditions. Its effects on the heart may provide insights into the treatment of arrhythmias or other heart-related issues.
Used in Neuromuscular Applications:
Piperovatine's action as a spinal cord stimulant in frogs suggests potential applications in neuromuscular research and the development of treatments for conditions involving muscle spasms or other neuromuscular dysfunctions.
Used in Toxicological Research:
The heart poison properties of piperovatine make it a valuable tool in toxicological research, helping to understand the mechanisms of action of various toxins and their effects on the cardiovascular system.
Used in Comparative Pharmacology:
The similarity of piperovatine's induced tonic spasm to that of strychnine offers opportunities for comparative pharmacological studies, which may lead to a better understanding of the underlying mechanisms and potential therapeutic applications.
References
Dunstan, Garnett., J. Chern. Soc., 67, 94 (1895)
Price, Pinder., J. Org. Chern., 35,2568 (1970)
Pharmacology:
Cash., J. Chern. Soc., 67,94 (1895)
Check Digit Verification of cas no
The CAS Registry Mumber 25090-18-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,0,9 and 0 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 25090-18:
(7*2)+(6*5)+(5*0)+(4*9)+(3*0)+(2*1)+(1*8)=90
90 % 10 = 0
So 25090-18-0 is a valid CAS Registry Number.
InChI:InChI=1/C17H23NO2/c1-14(2)13-18-17(19)8-6-4-5-7-15-9-11-16(20-3)12-10-15/h4-6,8-12,14H,7,13H2,1-3H3,(H,18,19)/b5-4+,8-6+
25090-18-0Relevant articles and documents
A NOVEL AND EFFICIENT METHOD TO PREPARE 3-(HETERO)ARYL-1-PROPYNES AND ITS APPLICATION TO THE STEREOSELECTIVE SYNTHESIS OF (2E,4E)-N-(2-METHYLPROPYL)-6-(2-METHYLPROPYL)-6-(2-THIENYL)-2,4-HEXADIENAMIDE, PIPEROVATINE AND (E)-N-(2-METHYLPROPYL)-6-(4-METHOXYPHENYL)-4-HEXYN-2-ENAMIDE
Rossi, Renzo,Carpita, Adriano,Lippolis, Vito,Benetti, Massimo
, p. 783 - 791 (2007/10/02)
Chemically pure 3-(hetero)aryl-1-propynes, 13, have been prepared in high overall yields by a novel method which involves: (a) a copper(I)-mediated cross-coupling between a halomethyl(hetero)arene, 16, and trimethylsilylethylmagnesium bromide, 17, to give a trimethylsilyl-3-(hetero)aryl-1-propyne, 18; (b) removal of the trimethylsilyl group from 18 by treatment with potassium fluoride dihydrate in DMF.One of these 1-alkynes, i.e. 3-(2-thienyl)-1-propyne, 13a, has been employed in the key step of a highly stereoselective synthesis of naturally-occurring (2E,4E)-N-(2-methylpropyl)-6-(2-thienyl)-2,4-hexadienamide, 6.On the other hand, 3-(4-methoxyphenyl)-1-propyne, 13b, has been used either in two stereoselective syntheses of another natural N-(2-methylpropyl) amide, i.e. piperovatine, 7, or in the preparation of a structural analogue of 7, i.e. (E)-N-(2-methylpropyl)-6-(4-methoxyphenyl)-4-hexyn-2-enamide, 15.
A NOVEL APPLICATION OF MOLYBDENUM MEDIATED DIENE SYNTHESIS IN THE PREPARATION OF PIPEROVATINE
Blade, Robert J.,Robinson, J. Edward
, p. 3209 - 3210 (2007/10/02)
A novel regio- and stereoselective synthesis of the dienamide piperovatine is described.This method does not suffer from problems associated with doublebond migration.
