Phenyl-2-nitropropene

Last updated
1-Phenyl-2-nitropropene [1] [2] [3] [4] [5]
Phenyl-2-nitropropene.svg
P2NP Crystals.png
Phenyl-2-Nitropropene.png
Names
Preferred IUPAC name
(2-Nitroprop-1-en-1-yl)benzene
Other names
P2NP
1-Phenyl-2-nitropropene
β-methyl-β-nitropropene
trans-beta-Methyl-beta-Nitrostyrene
(2-Nitro-1-propenyl)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.731 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C9H9NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3/b8-7+ Yes check.svgY
    Key: WGSVFWFSJDAYBM-BQYQJAHWSA-N Yes check.svgY
  • InChI=1/C9H9NO2/c1-8(10(11)12)7-9-5-3-2-4-6-9/h2-7H,1H3/b8-7+
    Key: WGSVFWFSJDAYBM-BQYQJAHWBX
  • [O-][N+](=O)/C(=C/c1ccccc1)C
Properties
C9H9NO2
Molar mass 163.17 g mol−1
Appearancesolid
Melting point 64 to 66 °C (147 to 151 °F; 337 to 339 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362+P364
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1-Phenyl-2-nitropropene, or simply phenyl-2-nitropropene, or P2NP, as it is commonly referred to, is a chemical compound from the aromatic group of compounds, with the formula C9H9NO2. It is a light-yellow crystalline solid with a distinct smell. [6] Phenyl-2-nitropropene is used in the pharmaceutical industry to manufacture the drug Adderall, an amphetamine mixture used to treat ADHD and narcolepsy. P2NP and other similar nitrostyrenes are also employed in the clandestine manufacture of drugs of the amphetamine class, and are listed as drug precursors in many countries. [7] [8] [9]

Contents

Uses

In the pharmaceutical industry, P2NP is used to produce a racemic amphetamine mixture, branded under the trade names Adderall and Mydayis, amongst others. In this case, the double bond is hydrogenated and the nitro group is reduced, [10] thus 1-phenyl-2-nitropropene becomes 1-phenyl-2-aminopropane, which is another name for amphetamine. Different reducing agents commonly lithium aluminium hydride (LAH), sodium borohydride,aluminum amalgam or Raney nickel are used in suitable solvents like isopropyl alcohol or tetrahydrofuran.

Reduction of P2NP to Amphetamine Reduction of P2NP to Amphetamine.png
Reduction of P2NP to Amphetamine

The above diagram depicts P2NP reduction to amphetamine by either LAH, sodium amalgam, Raney nickel, or palladium used as catalysts. Platinum, in the form of Adams' catalyst, can also be used. [7]

P2NP can also be reduced to phenylacetone (P2P), the precursor in the synthesis of methamphetamine by a few methods. One in which phenyl-2-nitropropene is reduced to phenyl-2-nitropropane using sodium borohydride, followed by hydrolysis of the nitro group with hydrogen peroxide and potassium carbonate to produce phenylacetone (1-phenyl-2-propan-2-one). [11] In another method, iron is the reducing agent and hydrochloric acid or acetic acid are used as catalysts forming an intermediate which hydrolyzes into phenylacetone as well. [11]

Synthesis

In the lab, phenyl-2-nitropropene is produced by the reaction of benzaldehyde and nitroethane in the presence of a basic catalyst like n-butylamine. The reaction is a nitroaldol reaction, and is a variant of a Knoevenagel condensation reaction, which is one of a broader class of reactions called Henry condensations, or simply Henry reactions. These are named after the German chemist Emil Knoevenagel, and the Belgian chemist Louis Henry, respectively.

Synthesis of phenyl-2-nitropropene Creation of phenyl-2-nitropropene.svg
Synthesis of phenyl-2-nitropropene

In this type of reaction, the basic catalyst deprotonates the nitroethane to form a resonance stabilized anion. This anion nucleophilically adds to the aldehyde forming a β-nitro alcohol, which is subsequently dehydrated to yield the nitroalkene. Water is produced as a byproduct, and must be actively removed from the reaction mixture. Often, primary amines like n-butylamine, methylamine, and ethylamine are used as catalysts, as is anhydrous ammonium acetate at times. [6]

Many other drugs of the amphetamine class are produced in a similar fashion, where substituted benzaldehyde derivatives are used to produce a different nitrostyrene, which is later reduced to the desired amine. One such reaction is the Knoevenagel condensation of piperonal with nitroethane, yielding 3,4-methylenedioxy-1-phenyl-2-nitropropene, or MDP2NP. This is reduced to 3,4-methylenedioxyamphetamine, or MDA, which can be methylated to 3,4-methylenedioxymethamphetamine, or MDMA. [9] Another uses 2,5-dimethoxybenzaldehyde and nitromethane to yield 2,5-dimethoxy-β-nitrostyrene. Many of these Knoevenagel condensations were used by Dr. Alexander Shulgin to yield over 100 amphetamine derivatives, which he detailed in his book, PiHKAL . [12] [6] [13]

Safety and Storage

P2NP is labeled as harmful by the GHS, and is a known irritant. Thus, breathing fumes and direct skin and eye contact should be avoided. The median lethal dose for oral exposure in rats and mice is greater than 500 mg/kg and 1176 mg/kg, respectively. Based on available data, the classification criteria are not met to classify P2NP as a carcinogen. However, the toxicological properties have not been thoroughly investigated. [3] [4] [2]

P2NP should be stored at 2 °C to 8 °C and away from strong oxidizing agents. At higher temperatures, P2NP is not very stable, and degrades with time. [4] [6]

Related Research Articles

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by chemists at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Michael addition reaction</span> Reaction in organic chemistry

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

<span class="mw-page-title-main">Misuse of Drugs Act (Singapore)</span> Law of Singapore

The Misuse of Drugs Act 1973 is a statute of the Parliament of Singapore that enables authorities to prosecute offenders for crimes involving illegal drugs. The law is designed specifically to grant the Government of Singapore, though its agencies such as the Central Narcotics Bureau, enforcement powers to combat offences such as the trafficking, importation or exportation, possession, and consumption of controlled drugs.

<span class="mw-page-title-main">Phenylacetone</span> Chemical compound

Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.

Phenylacetones are a group of organic compounds containing a phenyl moiety and an acetone moiety bonded together, the archetypal example being phenylacetone.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

The Étard reaction is a chemical reaction that involves the direct oxidation of an aromatic or heterocyclic bound methyl group to an aldehyde using chromyl chloride. For example, toluene can be oxidized to benzaldehyde.

<span class="mw-page-title-main">Nitroethane</span> Chemical compound

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.

<span class="mw-page-title-main">Fencamfamin</span> Chemical compound

Fencamfamin (INN), also known as fencamfamine or by the brand names Glucoenergan and Reactivan, is a stimulant which was developed by Merck in the 1960s.

<span class="mw-page-title-main">3C-BZ</span> Chemical compound

3C-BZ (4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 25–200 mg and the duration as 18–24 hours. According to anecdotal reports from the substance's entry in PiHKAL, 3C-BZ's effects can vary significantly, ranging from intensified emotions and strange dreams, to effects similar to those of LSD or TMA. Very little data exists about the pharmacological properties, metabolism, and toxicity of 3C-BZ.

<span class="mw-page-title-main">DMMDA</span> Psychedelic drug

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours. He reported DMMDA as producing LSD-like images, mydriasis, ataxia, and time dilation.

<span class="mw-page-title-main">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</span>

The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.

<span class="mw-page-title-main">AL-1095</span> Stimulant drug

AL-1095, is a centrally acting stimulant drug with comparable effects to amphetamine, developed by Bristol in the 1970s.

Drug precursors, also referred to as precursor chemicals or simply precursors, are substances used to manufacture illicit drugs. Most precursors also have legitimate commercial uses and are legally used in a wide variety of industrial processes and consumer products, such as medicines, flavourings, and fragrances.

<span class="mw-page-title-main">2-Hydroxy-5-methoxybenzaldehyde</span> Organic compound and isomer of vanillin

2-Hydroxy-5-methoxybenzaldehyde is an organic compound and an isomer of vanillin.

<i>beta</i>-Nitrostyrene Chemical compound

β-Nitrostyrene is an aromatic compound and a nitroalkene used in the synthesis of indigo dye and the slimicide bromo-nitrostyrene.

References

  1. ↑ Alfa Aesar entry on 2-Nitro-1-phenylpropene , accessed on March 20, 2021
  2. 1 2 Material Safety Data Sheet trans-β-Methyl-β-nitrostyrene (PDF) from Sigma-Aldrich, accessed on March 20, 2021
  3. 1 2 Material Safety Data Sheet P2NP (PDF) from Cayman Chemical, accessed on March 20, 2021
  4. 1 2 3 Material Safety Data Sheet 1-(Phenyl)2-nitropropene (PDF) from Biosynth Carbosynth, accessed on March 20, 2021
  5. ↑ "Chemical Book" Website - entry on 1-Phenyl-2-nitropropene, accessed on March 21, 2021
  6. 1 2 3 4 Phenyl-2-nitropropene synthesis via Ammonium acetate catalysis, 2021
  7. 1 2 Synthetic Reductions in Clandestine Amphetamine and Methamphetamine Laboratories - A Review
  8. ↑ Urushibara Style Amphetamine
  9. 1 2 3,4-Methylenedioxyphenyl-2-Nitropropene From Piperonal, Nitroethane & NaOH
  10. ↑ Организация Объединённых Наций (2007). "Синтез амфетамина. Восстановительное аминирование (каталическое восстановление с использованием металла)". Рекомендуемые методы обнаружения и анализа амфетамина, метамфетамина и их замещённых по циклу аналогов в конфискованных материалах. Нью-Йорк. p. 12. ISBN   9789214480303.{{cite book}}: CS1 maint: location missing publisher (link)
  11. 1 2 Phenyl-2-Propanone from Phenyl-2-Nitropropene #8
  12. ↑ Pihkal: A Chemical Love Story, Alexander Shulgin and Ann Shulgin, 1991
  13. ↑ Erowid, phenyl-2-nitropropene
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.