Names | |
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Preferred IUPAC name 4,7-Dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole | |
Other names 5-Allyl-4,7-dimethoxybenzo[d][1,3]dioxole 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.007.592 |
EC Number |
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KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C12H14O4 | |
Molar mass | 222.23 g/mol |
Density | 1.151 g/mL |
Melting point | 30 °C (86 °F; 303 K) |
Boiling point | 294 °C (561 °F; 567 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Apiole is a phenylpropene, also known as apiol, parsley apiol, or parsley camphor. Its chemical name is 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. It is found in the essential oils of celery leaf and all parts of parsley. [1] Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. [2] In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation.
In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders and as an abortifacient. It is an irritant and, in high doses, it can cause liver and kidney damage. [3] Cases of death due to attempted abortion using apiole have been reported. [4] [5]
Hippocrates wrote about parsley as an herb to cause an abortion. [6] Plants containing apiole were used by women in the Middle Ages to terminate pregnancies. Now that safer methods of abortion are available, apiol is almost forgotten.
Apiole (always with the final 'e') is the correct spelling[ citation needed ] of the trivial name for 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. [7] Apiol, also known as liquid apiol or green oil of parsley, is the extracted oleoresin of parsley, rather than the distilled oil. Its use was widespread in the United States, often as ergoapiol or apergol, as an early form of birth control as well as for menstrual issues (and off label for abortions)until a highly toxic adulterated product containing apiol and tri-ortho-cresyl phosphate (also famous as the adulterant added to Jamaican ginger) was introduced on the American market. 1'-sulfoxy metabolite formation for apiole (3,4-OMe-safrole) is about 1/3 as active as safrole. [8] No carcinogenicity was detected with parsley apiol or dill apiol in mice. [9]
The name apiole is also used for a closely related compound found in dill and in fennel roots, the positional isomer (dillapiole, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene. Exalatacin (1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene) is another positional isomer of apiole, found in the Australian plants Crowea exalata and Crowea angustifolia var. angustifolia.[ citation needed ]
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."
Safrole is an organic compound with the formula CH2O2C6H3CH2CH=CH2. It is a colorless oily liquid, although impure samples can appear yellow. A member of the phenylpropanoid family of natural products, it is found in sassafras plants, among others. Small amounts are found in a wide variety of plants, where it functions as a natural antifeedant. Ocotea pretiosa, which grows in Brazil, and Sassafras albidum, which grows in eastern North America, are the main natural sources of safrole. It has a characteristic "sweet-shop" aroma.
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.
The Controlled Drugs and Substances Act is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeals the Narcotic Control Act and Parts III and IV of the Food and Drugs Act, and establishes eight Schedules of controlled substances and two Classes of precursors. It provides that "The Governor in Council may, by order, amend any of Schedules I to VIII by adding to them or deleting from them any item or portion of an item, where the Governor in Council deems the amendment to be necessary in the public interest."
Apiol, also known as liquid apiol or green oil of parsley is the extracted oleoresin of parsley, rather than the distilled oil. Due to its similarity to the term apiole, care should be taken to avoid confusion. Apiol is an irritant and, in high doses, it can cause liver and kidney damage. Cases of death due to attempted abortion using apiol have been reported.
2C-G is a psychedelic phenethylamine of the 2C-series. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in PiHKAL, 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects.
2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.
Elemicin is a phenylpropene, a natural organic compound, and is a constituent of several plant species' essential oils.
Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.
Dillapiole is an organic chemical compound and essential oil commonly extracted from dill weed, though it can be found in a variety of other plants such as fennel root. This compound is closely related to apiole, having a methoxy group positioned differently on the benzene ring. Dillapiole works synergically with certain insecticides like pyrethrins similarly to piperonyl butoxide, which likely results from inhibition of the MFO enzyme of insects.
Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant. Other uses include as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics and as an antiwear additive in lubricants. Pure tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol, though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, especially the all-ortho isomer, is the causative agent in a number of acute poisonings. Its chronic toxicity is also of concern. The ortho-isomer is rarely used on its own outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.
Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.
Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL. Little is known about their dangers or toxicity.
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.
Magnoliids are a clade of flowering plants. With more than 10,000 species, including magnolias, nutmeg, bay laurel, cinnamon, avocado, black pepper, tulip tree and many others, it is the third-largest group of angiosperms after the eudicots and monocots. The group is characterized by trimerous flowers, pollen with one pore, and usually branching-veined leaves.
These drugs are known in the UK as controlled drug, because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other drugs which are controlled by the Medicines Act but not by the Misuse of Drugs Act, and some other drugs are controlled by other laws.
Petroselinic acid is a fatty acid that occurs naturally in several animal and vegetable fats and oils. It is a white powder and is commercially available. In chemical terms, petroselinic acid is classified as a monounsaturated omega-12 fatty acid, abbreviated with a lipid number of 18:1 cis-6. It has the formula CH3(CH2)10CH=CH(CH2)4COOH. The term "petroselinic" means related to, or derived from, oil of Petroselinum, parsley. Despite its name, petroselinic acid does not contain any selenium. Petroselinic acid is a positional isomer of oleic acid.
Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.
The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.