Antrafenine (Stakane) is a
phenylpiperazine
1-Phenylpiperazine is a simple chemical compound featuring a phenyl group bound to a piperazine ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.
List phenylpiperazine derivativesAlp ...
derivative
In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...
drug
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...
invented in 1979.
It acts as an
analgesic
An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...
and
anti-inflammatory
Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as o ...
drug with similar efficacy to
naproxen
Naproxen is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulati ...
,
but is not widely used as it has largely been replaced by newer drugs.
Synthesis
Method E: The reaction between 2-
-[3-(trifluoromethyl)phenyl1-piperazinyl.html" ;"title="-(trifluoromethyl)phenyl.html" ;"title="-[3-(trifluoromethyl)phenyl">-[3-(trifluoromethyl)phenyl1-piperazinyl">-(trifluoromethyl)phenyl.html" ;"title="-[3-(trifluoromethyl)phenyl">-[3-(trifluoromethyl)phenyl1-piperazinylthanol [40004-29-3] (1) and Isatoic anhydride [118-48-9] (2) goes on to give 4-(3-(Trifluoromethyl)phenyl)piperazine-1-ethyl 2-aminobenzoate [51941-08-3] (3).
Method G: Alkylation with 4-chloro-7-(trifluoromethyl)quinoline
46-55-4(4) completed the synthesis of antrafenine (5).
See also
*
Phenylpiperazine
1-Phenylpiperazine is a simple chemical compound featuring a phenyl group bound to a piperazine ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.
List phenylpiperazine derivativesAlp ...
*
Trifluoromethylphenylpiperazine
3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the piperazine chemical class. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").
Pharm ...
References
meta-Trifluoromethylphenylpiperazines
Anthranilates
Quinolines
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