What is alpha-phenylacetoacetonitrile (APAN)?
APAN (also called: apane) or alpha-phenylacetoacetonitrile is an organic compound used in the preparation of certain drugs. APAAN contains a nitrile group and a benzene ring (phenyl group).
The tissue is, as a precursor pre – drug, used to make the tissue of phenylacetone (which is also known as BMK = B Benzyl M ethyl K Eton), and these are the methamphetamine and amphetamine stimulants performed. There are also other ways to make methamphetamine. In particular, the United States Department of State mentions the Netherlands as a place where APAAN is used. The European Monitoring Center for Drugs and Drug Addiction (EMCDDA) mentions in particular Poland.
Importance and usefulness of the product (alpha-phenylacetoacetonitrile )
Alpha-phenylacetoacetonitrile has become an important precursor for the illicit synthesis of amphetamines and its importance is increasing.
APAAN has been observed during seizures in the Netherlands, Poland and Germany. One of the reasons for the increasing importance of APAAN is that the conversion to benzyl methyl ketone (BMK) can be carried out very easily using a simple production method, which achieves high yields.
The conversion of APAAN to BMK is mainly carried out in laboratories located in the Netherlands and Poland. Although widely used for the illicit production of BMK, from a medico-legal point of view, there is still a lack of knowledge on APAAN, its purity, the various conversion processes, the yields and the impurities characteristic of BMK.
Α-Phenylacetoacetonitrile (APAAN) is one of the most important precursors for the production of amphetamines in recent years.
This assumption is based on the input data, but there is little analytical data available showing how much amphetamine actually came from APAAN. In this study, various syntheses of amphetamines were carried out following the Leuckart route from various organic compounds, including APAAN.
The organic phases were analyzed using gas chromatography-mass spectrometry (GC-MS) to look for signals caused by possible APAAN markers. Three compounds have been discovered, isolated and have been found to be very specific for APAAN use based on the syntheses carried out.
Using mass spectra, high resolution MS data and nuclear magnetic resonance (NMR), the compounds were characterized and identified as 2-phenyl-2-butenonitrile, 3-amino-2-phenyl-2 -butenonitrile and 4-amino-6-methyl -5-phenylpyrimidine. To investigate their significance, data from the seized amphetamine samples were searched to determine the extent to which they were present in the illicitly produced amphetamine. Data from more than 580 cases from amphetamine profiling databases in Germany and the Netherlands were used for this purpose
Buy Alpha-phenylacetoacetonitrile
α-Phenylacetoacetonitrile, Useful product for research
α-Phenylacetoacetonitrile (APAAN; Item No. 21105) is an analytical reference standard that is structurally categorized as an amphetamine precursor. APAAN is used to generate phenylacetone (Item Nos. 16103 | 16444), which is then modified by the Leuckart reaction to synthesize amphetamine.1,2 This product is intended for research and forensic applications.
Methods for the Preparation of Organic Compounds ( α-PHENYLACETOACETONITRILE )
1. Procedure
A solution of sodium ethoxide is prepared from 60 g. (2.6 gram atoms) of clean sodium and 700 cc. of absolute alcohol (Note 1) in a 2-l. round-bottomed flask equipped with a reflux condenser. To the hot solution is added a mixture of 234 g. (2 moles) of pure benzyl cyanide (Note 2) and 264 g. (3 moles) of dry ethyl acetate (Note 3). The mixture is thoroughly shaken, the condenser closed with a calcium chloride tube, and the solution heated on the steam bath for two hours before standing overnight (Note 4). The next morning the mixture is stirred with a wooden rod to break lumps, cooled in a freezing mixture to −10°, and kept at this temperature for two hours. The sodium salt is collected on a 6-in. Büchner funnel and washed four times on the funnel with 250-cc. portions of ether. The filter cake is practically colorless and corresponds to 250–275 g. of dry sodium salt, or 69–76 per cent of the calculated amount. The combined filtrates are placed in the freezing mixture until they can be worked up as indicated below.
The sodium salt still wet with ether is dissolved in 1.3 l. of distilled water at room temperature, the solution cooled to 0°, and the nitrile precipitated by adding slowly, with vigorous shaking, 90 cc. of glacial acetic acid, while the temperature is kept below 10°. The precipitate is separated by suction filtration and washed four times on the funnel with 250-cc. portions of water. The moist cake weighing about 300 g. (Note 5) corresponds to 188–206 g. (59–64 per cent) of dry colorless α-phenylacetoacetonitrile, m.p. 87–89°, which is suitable for most purposes.
If it is desired to recrystallize the crude product, the moist cake is dissolved in 100 cc. of hot methyl alcohol and the solution filtered and cooled, with stirring, to −10°. The crystals are separated by suction filtration and washed once on the filter with 40 cc. of methyl alcohol cooled to −10°. When dry, the product weighs 173–191 g. (54–60 per cent) and melts at 88.5–89.5°.
The filtrates and washings from the separation of the sodium salt are placed in a 5-l. flask and diluted with ice-cold water until the flask is full; the lower layer is removed almost completely by siphoning, most of the ether removed by decantation, and the remainder separated in a separatory funnel. The aqueous layer is extracted twice in a similar manner with 500-cc. portions of ether, and the ether extracts are discarded. The ether remaining in the aqueous layer is removed under diminished pressure by drawing air through the solution for one hour with a suction pump, and the α-phenylacetoacetonitrile is precipitated by adding 60 cc. of glacial acetic acid. If an oil is thrown out, the flask is placed in an ice bath until the precipitate is crystalline. The crystals are separated by suction filtration and washed four times on the funnel with 50-cc. portions of water. When dry the tan-colored product weighs 50–55 g. and melts at 83–86°. It is dissolved in the methyl alcohol mother liquors from the crystallization of the first lot. The solution is boiled with a little Norite, filtered, and cooled to −10°. The crystals which form are collected on a filter, washed with 10 cc. of cold methyl alcohol, and dried. There is obtained 43–48 g. of pale straw-colored material, m.p. 87–89°. The product is recrystallized from 25 cc. of pure methyl alcohol and washed with 10 cc. of cold methyl alcohol; there is obtained 37–41 g., m.p. 88.5–89.5°, making a total yield of material of this purity of 210–232 g. (66–73 per cent of the theoretical amount) (Note 6) and (Note 7).
Synonyms or derived products :
APAAN
2-phenylacetoacetonitrile
NSC 11777
NSC 25183
NSC 55206
alpha-phenylacetoacetonitrile
Experience and testimony of a research enthusiast on alpha-phenylacetoacetonitrile, in a forum.
So, thru the help of many of the chemists on these forums, I have managed to synthesize a fairly good amount of phenylacetonitrile. From that, via sodium ethoxide and anhydrous ethyl acetate i have successfully made the sodium salt that comes from this. I literally spent hours drying it on the vacuum pump, did not have diethyl ether….well I did…but I opted to use dcm because it is much easier to produce obviously and much safer in my estimation cancer considerations aside. So, I get to the point where I have this moist sodium salt, that has been washed with dcm, so I add water to it to get it into solution, place it in a freezing mixture made of water, salt, ice, acetone and methanol, get the temperature down to around -5 C. Ok, so I go to add the glacial acetic acid…..add it in and nothing…..its almost as if the sodium salt has disappeared. I know the salt is in there because I added it to water an hour prior, but adding the glacial acetic acid does not seem to precipitate it. I thought maybe its not cold enough do I threw it back in the freezing mixture to see if anything would fall out but nothing. I have tried adding straight glacial acetic acid as well as diluted glacial acetic acid. Kinda miffed here. Does anyone have any advice.
α-Phenylacetoacetonitrile, Censored and Controlled Product
Decision 57/1
Inclusion of alpha-phenylacetoacetonitrile and its
optical isomers in Table I of the United Nations
Convention against Illicit Traffic in Narcotic Drugs and
Psychotropic Substances of 1988
At its 9th meeting, on 19 March 2014, the Commission on Narcotic
Drugs decided by 40 votes to none, with no abstentions, to include alphaphenylacetoacetonitrile and its optical isomers in Table I of the United
Nations Convention against Illicit Traffic in Narcotic Drugs and
Psychotropic Substances of 1988.