N-Methylconiine

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N-Methylconiine
Nme-coniine.svg
Names
IUPAC name
1-Methyl-2-propylpiperidine
Identifiers
3D model (JSmol)
3DMet
79936
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
Properties
C9H19N
Molar mass 141.258 g·mol−1
Density (d) 0.8318 g cm−3 at 24.3 °C

(l) 0.8349 g cm−3 at 20 °C

Boiling point 173 to 174 °C (343 to 345 °F; 446 to 447 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

N-Methylconiine is a poisonous alkaloid found in poison hemlock in small quantities.

Contents

Isolation and properties

The d-(+)-stereoisomer of N-methylconiine is reported to occur in hemlock in small quantities, [1] and methods for its isolation are described by Wolffenstein [2] and by von Braun. [3] It is a colourless, oily, coniine-like liquid, specific rotation [α]D +81.33° at 24.3 °C. The salts are crystalline ("B" marks one molecule of the base): the hydrochloride, B•HCl, forms masses of needles, mp. 188 °C; the platinichloride, B2•H2PtCl6, has mp. 158 °C.

The l-(−)-stereoisomer was obtained by Ahrens [4] from residues left in the isolation of coniine as hydrobromide or by removing coniine as the nitroso-compound. It is a colourless, coniine-like liquid, bp. 175.6 °C/767 mmHg, specific rotation [α]D −81.92° at 20 °C. The monohydrochloride crystallises in leaflets, mp. 191–192 °C; the monohydrobromide in leaflets, mp. 189–190 °C; the platinichloride in orange crystals, mp. 153–154 °C; the aurichloride in leaflets, mp. 77–78 °C; and the picrate in long needles, mp. 121–122 °C.

Synthesis

N-Methyl-d-coniine was prepared by the action of potassium methyl sulfate on coniine by Passon. [5] Hess and Eichel [6] have shown that d-coniine with formaldehyde and formic acid yields an active N-methyl-d-coniine, and that methyl-isopelletierine hydrazone yields N-methyl-dl-coniine when heated with sodium ethoxide at 150–170 °C.

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n
H
2n
O
n
. They are usually colorless, water-soluble, and crystalline solids. Some monosaccharides have a sweet taste.

Stereoisomerism isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

Optical rotation term

Optical rotation, also known as polarization rotation or circular birefringence, is the rotation of the orientation of the plane of polarization about the optical axis of linearly polarized light as it travels through certain materials. Circular birefringence and circular dichroism are the manifestations of optical activity. Optical activity occurs only in chiral materials, those lacking microscopic mirror symmetry. Unlike other sources of birefringence which alter a beam's state of polarization, optical activity can be observed in fluids. This can include gases or solutions of chiral molecules such as sugars, molecules with helical secondary structure such as some proteins, and also chiral liquid crystals. It can also be observed in chiral solids such as certain crystals with a rotation between adjacent crystal planes or metamaterials.

Hexose monosaccharide consisting of six carbon atoms

In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol.

Ethane is an organic chemical compound with chemical formula C
2
H
6
. At standard temperature and pressure, ethane is a colorless, odorless gas. Like many hydrocarbons, ethane is isolated on an industrial scale from natural gas and as a petrochemical by-product of petroleum refining. Its chief use is as feedstock for ethylene production.

Inverted sugar syrup is an edible mixture of two simple sugars—glucose and fructose—that is made by heating sucrose with water. It is thought to be sweeter than table sugar, and foods that contain it retain moisture better and crystallize less easily. Bakers, who call it invert syrup, may use it more than other sweeteners.

Coniine chemical compound

Coniine refers to a poisonous chemical compound, an alkaloid present in and isolable from poison hemlock, where its presence has been a source of significant economic, medical, and historico-cultural interest; coniine is also produced by the yellow pitcher plant, and fool's parsley. Its ingestion and extended exposure are toxic to humans and all classes of livestock; its mechanism of poisoning involves disruption of the central nervous system, with death caused by respiratory paralysis. The biosynthesis of coniine contains as its penultimate step the non-enzymatic cyclisation of 5-oxooctylamine to γ-coniceine, a Schiff base differing from coniine only by its carbon-nitrogen double bond in the ring. This pathway results in natural coniine that is a mixture—a racemate—composed of two enantiomers, the stereoisomers (S)-(+)-coniine and (R)-(−)-coniine, depending on the direction taken by the chain that branches from the ring. Both enantiomers are toxic, with the (R)-enantiomer being the more biologically active and toxic of the two in general. Coniine holds a place in organic chemistry history as being the first of the important class of alkaloids to be synthesized, by Albert Ladenburg in 1886, and it has been synthesized in the laboratory in a number of unique ways through to modern times.

Diazomethane chemical compound

Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

Piperine chemical compound

Piperine, along with its isomer chavicine, is the alkaloid responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine.

Enantiomeric excess (ee) is a measurement of purity used for chiral substances. It reflects the degree to which a sample contains one enantiomer in greater amounts than the other. A racemic mixture has an ee of 0%, while a single completely pure enantiomer has an ee of 100%. A sample with 70% of one enantiomer and 30% of the other has an ee of 40%.

Phenylethanolamine chemical compound

Phenylethanolamine, or β-hydroxyphenethylamine, is a trace amine with a structure similar to those of other trace phenethylamines as well as the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. As an organic compound, phenylethanolamine is a β-hydroxylated phenethylamine that is also structurally related to a number of synthetic drugs in the substituted phenethylamine class. In common with these compounds, phenylethanolamine has strong cardiovascular activity and, under the name Apophedrin, has been used as a drug to produce topical vasoconstriction.

<i>Conium maculatum</i> poisonous herb in the carrot family

Conium maculatum, the hemlock or poison hemlock, is a highly poisonous biennial herbaceous flowering plant in the carrot family Apiaceae, native to Europe and North Africa. A hardy plant capable of living in a variety of environments, hemlock is widely naturalized in locations outside its native range, such as parts of North and South America, Australia and West Asia, to which it has been introduced.

Tetramethylammonium chloride chemical compound

Tetramethylammonium chloride is one of the simplest quaternary ammonium salts, with four methyl groups tetrahedrally attached to the central N. The chemical formula (CH3)4N+Cl is often abbreviated further as Me4N+Cl. It is a hygroscopic colourless solid that is soluble in water and polar organic solvents. Tetramethylammonium chloride is a major industrial chemical, being used widely as a chemical reagent and also as a low-residue bactericide in such processes as hydrofracking. In the laboratory, it has fewer synthetic chemical applications than quaternary ammonium salts containing longer N-alkyl substituents, which are used extensively as phase-transfer catalysts.

Syntin chemical compound

Syntin is a hydrocarbon with the molecular formula C10H16 used as a rocket fuel. It is a mixture of four stereoisomers (see below). It has a density of 0.851 g/mL, and a boiling point of 158 °C. Due to the presence of three strained cyclopropane rings, the molecule has a highly positive enthalpy of formation: ΔfH°(l)= 133 kJ/mol (980 kJ/kg, the average value for the isomeric mixture), bringing additional energy into the combustion process. It has advantages over the traditional hydrocarbon fuels, such as RP-1, due to higher density, lower viscosity and higher specific heat of oxidation.

Conhydrine chemical compound

Conhydrine is a poisonous alkaloid found in poison hemlock in small quantities.

Trimethylborane chemical compound

Trimethylborane (TMB) is a toxic, pyrophoric gas with the formula B(CH3)3 (which can also be written as Me3B, with Me representing methyl).

Halostachine chemical compound

Halostachine is a natural product, an alkaloid first isolated from the Asian shrub Halostachys caspica, and structurally a β-hydroxy-phenethylamine related to its better-known "parent" biogenic amine, phenylethanolamine, to the adrenergic drug synephrine, and to the alkaloid ephedrine. The pharmacological properties of halostachine have some similarity to those of these structurally-related compounds, and Halostachys caspica extracts have been included as a constituent of certain OTC dietary supplements, but halostachine has never been developed as a prescription drug. Although it is found in nature as a single stereoisomer, halostachine is more commonly available as a synthetic product in the form of its racemate. In appearance it is a colorless solid.

1-Tetralone chemical compound

1-Tetralone is a bicyclic aromatic hydrocarbon and a ketone. In terms of its structure, it can also be regarded as benzo-fused cyclohexanone. It is a colorless oil with a faint odor. It is used as starting material for agricultural and pharmaceutical agents. The carbon skeleton of 1-tetralone is found in natural products such as Aristelegone A (4,7-dimethyl-6-methoxy-1-tetralone) from the family of Aristolochiaceae used in traditional Chinese medicine.

5-Chloro-αMT chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

P4-t-Bu chemical compound

P4-t-Bu is a readily accessible chemical from the group of neutral, peralkylated sterically hindered polyaminophosphazenes, which are extremely strong bases but very weak nucleophiles. P4-t-Bu can also be regarded as tetrameric triaminoiminophosphorane of the basic structure (H2N)3P=N-H. The homologous series of P1 to P7 polyaminophosphazenes of the general formula with preferably methyl groups as R1, a methyl group or tert.-butyl group as and even-numbered x between 0 and 6 (P4-t-Bu: R1 = Me, R2 = t-Bu und x = 3) has been developed by Reinhard Schwesinger; the resulting phosphazene bases are therefore also referred to as Schwesinger superbases.

References

  1. Planta and Kekulé, Annalen, 1854, 89, 150.
  2. Ber., 1894, 27, 2615; 1895, 28, 302
  3. Ber., 1905, 38, 3108; 1917, 50, 1477.
  4. Ber., 1902, 35, 1330; cf. Löffler and Friedrich, ibid., 1909, 42, 107.
  5. Ber., 1891, 24, 1678.
  6. Ber., 1917, 50, 1386; 1919, 52, 1622; 1920, 53, 129.