trans-Isosafrole | |
cis-Isosafrole | |
Names | |
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Preferred IUPAC name 5-(Prop-1-enyl)-2H-1,3-benzodioxole | |
Other names 5-(1-Propenyl)-1,3-benzodioxole 3,4-Methylenedioxyphenyl-1-propene | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.010 |
EC Number |
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KEGG |
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PubChem CID | |
RTECS number |
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UNII |
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UN number | 3082 |
CompTox Dashboard (EPA) | |
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Properties | |
C10H10O2 | |
Molar mass | 162.188 g·mol−1 |
Density | 1.1206 g/cm3, trans 1.1182 g/cm3, cis |
Melting point | 8.2 °C (46.8 °F; 281.3 K) trans -21.5 °C, cis |
Boiling point | 255 °C (491 °F; 528 K) trans 243 °C, cis |
Hazards | |
GHS labelling: | |
Danger | |
H302, H315, H341, H350 | |
P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P405, P501 | |
Legal status | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Isosafrole is an organic compound that is used in the fragrance industry. Structurally, the molecule is related to allylbenzene, a type of aromatic organic chemical. Its fragrance is reminiscent of anise or licorice. It is found in small amounts in various essential oils, but is most commonly obtained by isomerizing the plant oil safrole. It exists as two geometric isomers, cis-isosafrole and trans-isosafrole.
Isosafrole is a precursor to the important fragrance piperonal. [3] It can also be converted via the intermediate compound MDP2P into the psychoactive drug MDMA ('ecstasy'). As such it requires permits to purchase or sell in any significant quantity in the US.
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.
Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Turbina corymbosa (ololiuhqui), Argyreia nervosa, and Ipomoea tricolor.
Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.
Phenylacetic acid, also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine. As a commercial chemical, because it can be used in the illicit production of phenylacetone, it is subject to controls in countries including the United States and China.
Isobutyl nitrite, C4H9NO2, is an alkyl nitrite, an ester of isobutanol and nitrous acid. Its chemical structure is (CH3)2CH-CH2-ONO.
Barbexaclone (Maliasin) is a salt compound of phenobarbital and levopropylhexedrine. It was introduced in 1965. It has been reported to be as effective as phenobarbital but better tolerated; however, as of 2004, these "promising results" had not yet been confirmed nor denied in controlled trials.
Vinylbital, also known as butylvinal, is a sedative hypnotic drug which is a barbiturate derivative. It was developed by Aktiebolaget Pharmacia in the 1950s.
Propiomazine, sold under the brand name Propavan among others, is an antihistamine which is used to treat insomnia and to produce sedation and relieve anxiety before or during surgery or other procedures and in combination with analgesics as well as during labor. Propiomazine is a phenothiazine, but is not used therapeutically as a neuroleptic because it does not block dopamine receptors well.
Allobarbital, also known as allobarbitone and branded as Dial, Cibalgine, or Dial-Ciba, is a barbiturate derivative invented in 1912 by Ernst Preiswerk and Ernst Grether working for CIBA. It was used primarily as an anticonvulsant although it has now largely been replaced by newer drugs with improved safety profiles. Other uses for allobarbital included as an adjutant to boost the activity of analgesic drugs, and use in the treatment of insomnia and anxiety.
Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects, mediated through a mixed agonist–antagonist action at the mu opioid receptor, its clinical use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors and/or sigma receptors.
Dimenoxadol (INN), or dimenoxadole (BAN), is an opioid analgesic which is a benzilic acid derivative, closely related to benactyzine. Further, the structure is similar to methadone and related compounds like dextropropoxyphene.
Oxypertine, sold under the brand name Oxypertine among others, is an antipsychotic medication of the tryptamine and phenylpiperazine groups which was previously used in the treatment of schizophrenia but is no longer marketed. It was also evaluated for the treatment of anxiety.
Methyldihydromorphine is a semi-synthetic opioid originally developed in Germany in 1936, controlled under both domestic law and UN conventions because of its possible potential for abuse. Methyldihydromorphine is related to heterocodeine and is not a synonym for dihydrocodeine or dihydroheterocodeine (6-methoxydihydromorphine).
N-Acetylanthranilic acid is an organic compound with the molecular formula C9H9NO3. It is an intermediate product in catabolism of quinaldine in Arthrobacter sp., and is further metabolized to anthranilic acid.
Dimetacrine, also known as dimethacrine and acripramine, is a tricyclic antidepressant (TCA) used in Europe and formerly in Japan for the treatment of depression. It has imipramine-like effects; though, in a double-blind clinical trial against imipramine, dimetacrine was found to have lower efficacy in comparison and produced more weight loss and abnormal liver tests.
Imipraminoxide, or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression.
Caroxazone is an antidepressant which was formerly used for the treatment of depression but is now no longer marketed. It acts as a reversible monoamine oxidase inhibitor (RIMA) of both MAO-A and MAO-B subtypes, with five-fold preference for the latter.
Norlevorphanol is an opioid analgesic of the morphinan family that was never marketed. It is the levo-isomer of 3-hydroxymorphinan (morphinan-3-ol). Norlevorphanol is a Schedule I Narcotic controlled substance in the United States with an ACSCN of 9634 and in 2014 it had an annual aggregate manufacturing quota of 52 grams. It is used as the hydrobromide and hydrochloride (0.870).
Helional is a chemical compound used as a perfume in soap and laundry detergent. Chemically it is an aldehyde with a hydrocinnamaldehyde motif; a structural element which is present in a number of other important commercial fragrances and odorants.
Norpipanone is an opioid analgesic related to methadone which was developed in Germany and distributed in Hungary, Argentina, and other countries. It had originally not been under international control but upon observation of case reports of addiction it was reviewed and shortly thereafter became a controlled substance. In the United States, it is a Schedule I controlled substance. The salts in use are the hydrobromide and hydrochloride (0.902).