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Z4349 is an
Esterification of L-glutamic acid 6-86-0(1) with ethanol gives Glutamic acid diethyl ester 6450-41-2(2). Lactam formation occurs on heating to give L-Pyroglutamic acid ethyl ester 149-65-7(3). The reduction of the ester with sodium borohydride gives L-Pyroglutaminol 7342-08-4(4). Treatment with methyl chloride gave (S)-(5-Oxopyrrolidin-2-yl)methyl methanesulfonate 3288-20-1(5). Displacement of the leaving group with cyanide led to (S)-5-Oxo-2-pyrrolidineacetonitrile 2479-06-2(6). Catalytic reduction over Rosenmund catalyst in the presence of dimethylamine led to (5S)-5-
opioid
Opioids are a class of Drug, drugs that derive from, or mimic, natural substances found in the Papaver somniferum, opium poppy plant. Opioids work on opioid receptors in the brain and other organs to produce a variety of morphine-like effects, ...
analgesic drug developed in the 1990s by the pharmaceutical company Zambon
Zambon is an Italian company that has been operating in the pharmaceutical and fine chemical industry since 1906. The company is currently run by Elena Zambon who is the daughter of the founder.{{Cite news, url=http://www.repubblica.it/economia/ ...
. It is a derivative of an older drug viminol
Viminol (marketed under the brandname Dividol) is an opioid analgesic developed by a team at the drug company Zambon in the 1960s. Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids.
Viminol has both an ...
, which has been modified to improve potency and metabolic stability. In tests on mice it was found to be several hundred times the potency of morphine
Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...
.Synthesis
Esterification of L-glutamic acid 6-86-0(1) with ethanol gives Glutamic acid diethyl ester 6450-41-2(2). Lactam formation occurs on heating to give L-Pyroglutamic acid ethyl ester 149-65-7(3). The reduction of the ester with sodium borohydride gives L-Pyroglutaminol 7342-08-4(4). Treatment with methyl chloride gave (S)-(5-Oxopyrrolidin-2-yl)methyl methanesulfonate 3288-20-1(5). Displacement of the leaving group with cyanide led to (S)-5-Oxo-2-pyrrolidineacetonitrile 2479-06-2(6). Catalytic reduction over Rosenmund catalyst in the presence of dimethylamine led to (5S)-5--(dimethylamino)ethyl
The symbol , known in Unicode as hyphen-minus, is the form of hyphen most commonly used in digital documents. On most keyboards, it is the only character that resembles a minus sign or a dash, so it is also used for these. The name ''hyphen-min ...
yrrolidin-2-one, PC13306712 (7). Oxidation in the presence of hydrogen peroxide formed the N-oxide (8). Elimination of the amino group in the presence of weak base led to (S)-5-Vinylpyrrolidin-2-one 3288-23-4(9). Alkylation of the amino group with 2-Chlorobenzyl chloride 11-19-8(10) in the presence of sodium hydride base led to (5S)-1- 2-chlorophenyl)methyl5-ethenylpyrrolidin-2-one, PC56976994 (11). Treatment of the vinyl group with peroxy acid gave the oxirane. (5S)-1- 2-chlorophenyl)methyl5-(oxiran-2-yl)pyrrolidin-2-one, PC88496451 (12). Treatment with (2R)-N- 2R)-butan-2-ylutan-2-amine, PC6347588 (13) completed the synthesis of Z4349 (14).See also
*2F-Viminol
2F-Viminol is a pyrrole derived opioid analgesic drug, which was originally developed by a team at the drug company Zambon in the 1960s. It is around twice as potent as the parent compound viminol, though unlike viminol, 2F-viminol has never pas ...
* Desnitroetonitazene
References
Designer drugs Opioids 2-Chlorophenyl compounds Lactams Pyrrolidones Sec-Butyl compounds {{Analgesic-stub