Asarones

ASARONE 70-80% of calamus oil. In trace amounts in Asian carrot seed and clove bud oils. 

Asarylic aldehyde, C oH,204, is present in calamus oil, and also results from the oxidation of asarone. It has the constitution—... 

When the aldehyde is heated on the water-bath with 25 per cent, hydrochloric acid, it yields a triphenylmethane derivative, nonamethoxy-triphenylmethane, a body consisting of snow-white crystals, melting at 184 5°. The action of concentrated nitric acid upon the solution in glacial acetic acid of this triphenylmethane derivative gives rise to 1, 2, 5-trimethoxy-4-nitrobenzene (melting at 130°). With bromine, nonamethoxytriphenylmethane combines, with separation of a molecule of trimethoxy bromobenzene, into a tribromo additive compound of hexamethoxy diphenylmethane, a deep violet-blue body. The 1, 2, 5-tri-methoxy-4-bromobenzene (melting at 54 5°) may be obtained more readily from asaronic acid. 

Asarone, or 4-propenyl-l. 2.5. trimethoxybenzene, Cj Hj Og, is the trimethyl ether of a triphenol, which is found occurring naturally in the essential oil of Asarum arifolium, and to a small extent in matico and acorus oils. It is an aromatic crystalline compound having the following characters —... 

By oxidation asarone yields asarylic aldehyde, CgH2(CHO)(OCH3)g, melting at 114°, and finally asarylic acid, CgH2(COOH)(OCH3)3, melting at 144°. This acid is, of course, identical with trimethoxy-benzoic acid. 

Elemioin is isomeric with asarone. It is 4-allyl-l. 2.6-trimethoxy-benzene, and is found in the essential oil of Manila elemi. Its characters are as follows —... 

Asarumkampher, m. asarum camphor, asaron Asbest, m. asbestos. 

Add a saturated solution of 40 g Na nitrite to 10 g asarone in 90 ml ether. Add dropwise over four hours 75 ml 20% sulfuric acid with stirring. Let stand eight hours filter and wash precipitate with water, ether, ethanol, and dry. Dissolve 10 g precipitate in 60 ml 8% K... 

The root of the plant Acorus calamus (also called flag root and sweet calomel), which grows over much of the world, is chewed by the Cree Indians of Canada to produce psychedelic effects. The active compound seems to be asarone — a precursor in an hallucinogenic amphetamine. 

Asarone Sd EO 23 pj. pQ Qg%DC090 Ascorbic acid, dehydro Rt 2 C244 Ascorbic acid Rt 2093 Aspartic acid pH iei Astragalin Sd ... 

The plant occurs in polyploid varieties and the corresponding essential oils differ predominantly in their content of /3-asarone (cw-isoasarone) [5273-86-9] ... 

Calamus oil is used in perfumery for spicy-herbaceous notes small quantities are also employed in the alcoholic beverage industry. However, use is legally restricted because of the potential toxicity of /3-asarone. For determination of /3-asarone content in calamus oil see [295]. FCT 1977 (15) p. 623 [8015-79-0], [84775-39-3],... 

The catches of carrot flies in yellow sticky traps are enhanced by the release of hexanal and compounds isolated from the surface wax of carrot leaves i.e., trans-methyliso-eugenol and trans-asarone (28,29). The propenylbenzenes also stimulate oviposition by this insect (29). 

Calamus Acorus calamus L. (3-Asarone diploid variety (0), triploid variety (0-10), tetra-ploid variety (up to 96%)... 

Acorns calamus L. var. angustatus Besser A. gramineus Ait. A. tatarinowii L. Chang Pu (Sweet flag) (leaf, root) Acoric acid, beta-asarone, yellow bitter aromatic volatile oil, alpha-pinene, d-camphene, calamene, calamenol, calamenone.50,357-450 Anticonvulsant, analgesic, aphrodisiac, carminative, contraceptive, dessicant, diaphoretic. 

Daucus carota L. subsp. sative Hoffm. Nan He Chi (Carrot) (whole plant) Carotenes, lycopene, phytofluere, umbelliferone, alpha-pinene, camphene, myrcene, daucol, alpha-phellandrene, bisabolene, luteolin-7-glucoside, daucine, pyrrolidine, geraniol, citronellol, carotol, citral, caryophyllene, p-cymene, asarone, daucosterol, petroselinic acid.48 For chronic dysentery, worms, carminative, diuretic, emmenagogue, lower blood sugar, prevent cancer, diabetes, dyspepsia and gout. 

N.A. Acoric acid, asarone, linalool, palmitic acid, methylamine, saponin, mucilage, sesquiterpenes.99 100 103 105 Used as a panacea. It is antibacterial, antifungal, antiseptic, antiamebic, antiprotozoal, a vermifuge. Treat digestive upset, fevers. 

Methylesculetol-6,7-dinicotinate (32) is useful as an antiinflammatory and vasodilator oflow toxicity (101). The synthesis of asarone [5555-15-1] (2,4,5-trimethoxy-l-propenylbenzene), which is used as a tranquilizer, has been patented (102). It occurs in calamus root, Acorns calamus L.y and is a chemosterilant for insects (103). 6,7-Dihydroxycoumarin-4-methylsulfonic acid and its salts are useful in the treatment of capillary permeability and fragility and for protecting oxidizable metabolites and drugs against biooxidation (104). Certain chromones derived from hydroxyhydroquinone, eg (33), and its salts, esters, and amides are valuable in the prophylactic treatment of asthma (105) (see Antiasthmatic agents). 2-Methoxy-6-multiprenyl-l,4-benzoquinones are intermediates in the microbiological synthesis of coenzyme Q compounds (106). 

The drug asarone, which comes from a plant, Acorus calamus (found in Asia, Europe, and North America) is chemically very similar to mescaline. The roots of this plant are chewed to produce a dose-dependent effect about 2 inches produces a mild euphoria, whereas nearly 10 inches produces hallucinations. In some cultures, wives will chew on the roots and collect their expectorant throughout the day for their husbands to enjoy later. Nothing says welcome home at the end of a hard day like a nice warm bowl of spit. 

Material A chemical related to mescaline and the amphetamines found in the roots of sweet flag ( Acorus calamus ) and Asarum spp. It is chemically the precusor of TMA-2 (2,4,5-trimethoxy-a-methyl-4,5-methylenedioxyphenylethylamine), a hallucinogen with 18 times the gram potency of mescaline. Asarone is converted to TMA-2 in the body by aminization which takes place shortly after ingestion. 

Effects A piece of dried root the thickness of a pencil and about 2 inches long provides stimulating and buoyant feelings. A piece 10 inches long acts as a mind alterant and hallucinogen. (See ASARONE.)... 

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