アドレノクロム
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/14 02:59:23」(JST)
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| Adrenochrome |
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IUPAC name
3-hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione
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| Identifiers |
| CAS number |
54-06-8 N |
| PubChem |
5898 |
| ChemSpider |
5687 Y |
| Jmol-3D images |
Image 1 |
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O=C1\C=C2/C(=C\C1=O)N(CC2O)C
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InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3 Y
Key: RPHLQSHHTJORHI-UHFFFAOYSA-N Y
InChI=1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
Key: RPHLQSHHTJORHI-UHFFFAOYAD
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| Properties |
| Molecular formula |
C9H9NO3 |
| Molar mass |
179.17 g mol−1 |
| Density |
3.264 g/cm³ |
| Boiling point |
(decomposes, 115-120 °C) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N (verify) (what is: Y/N?) |
| Infobox references |
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Adrenochrome (catecholamine o-quinone),[1] chemical formula C9H9NO3, is a compound produced by the oxidation of adrenaline (epinephrine). The derivative carbazochrome is a hemostatic medication. It is unrelated to chrome (chromium).
Contents
- 1 Chemistry
- 2 Effect on the brain
- 3 Law
- 4 In popular culture
- 5 References
- 6 External links
Chemistry
In vivo, adrenochrome is synthesized by the oxidation of epinephrine. In vitro, silver oxide (Ag2O) is used as an oxidizing agent.[2] Its presence is detected in solution by a pink color. The color turns brown upon polymerization.
Effect on the brain
Several small-scale studies (involving 15 or fewer test subjects) were done in the 50s and 60s, reporting that adrenochrome triggered psychotic reactions like thought disorder, derealization, and euphoria.[3] It has never been scientifically accepted, however, that adrenochrome has psychedelic properties.[4] Researchers Abram Hoffer and Humphry Osmond claimed that adrenochrome is a neurotoxic, psychotomimetic substance and may play a role in schizophrenia and other mental illnesses.[5] In what they called the "adrenochrome hypothesis",[6] they speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome.[7][8]
Law
Adrenochrome is uncontrolled in the United States. Thus, it is generally legal to buy, possess, and distribute (sell, trade or give). If sold as a supplement, sales must conform to U.S. supplement laws. If sold for consumption as a food or drug, sales are regulated by the FDA.[9]
In popular culture
- Adrenochrome is mentioned in The Doors of Perception by Aldous Huxley as "a product of the decomposition of adrenaline" that can "produce many of the symptoms observed in mescaline intoxication."
- Author Hunter S. Thompson mentions adrenochrome in his book Fear and Loathing in Las Vegas. In the book it is derived from a living donor's adrenal gland (“It's no good if you get it out of a corpse."). As such, it is purported to be very exotic, and very intense: "the first wave felt like a combination of mescaline and methedrine".[10] Thompson reported a significant perceived rise in body temperature that led to paralysis. The adrenochrome scene also appears in the novel's film adaptation. In the DVD commentary, director Terry Gilliam admits that his and Thompson's portrayal is a fictional exaggeration. In fact, Gilliam insists that the drug is entirely fictional and seems unaware of the existence of a substance with even a similar name. Thompson also mentions the substance in his book Fear and Loathing on the Campaign Trail '72.
- The harvesting of an adrenal gland from a live victim to obtain Adrenochrome for drug abuse is a plot feature in the episode "Whom the Gods would Destroy" of the British TV series Lewis (2008).[11]
- Adrenochrome is a song by British band The Sisters of Mercy, originally released on their 1982 single Body Electric, and subsequently on their compilation album Some Girls Wander by Mistake. The band You Shriek released a cover in April 2012.
- Adrenochrome Dreams is a song by the heavy metal band Otep, originally released as a hidden track on their 2007 album The Ascension.
- Appetite for Adrenochrome is the title of the debut album by Sacramento, California pop-punk band the Groovie Ghoulies.
- Adrenochrome is a song by the band Emeralds, released on their 2012 album, Just to Feel Anything.
- Adrenochrome is the title of a 2013 album by Italian electronic group XP8.
- Drencrom is sold in one of the milk plus varieties in A Clockwork Orange at the Korova Milk Bar. In the film, it supposedly helps you to be "ultra-violent".
References
- ^ COMMENTARY, John Smythies; Neurochemistry Section, Brain and Perception Laboratory, Center for Human Information Processing, UCSD Association for the Scientific Study of Consciousness, Electronic Seminars, 1999
- ^ MacCarthy, Chim, Ind. Paris 55,435(1946)
- ^ John Smythies (2002). "The adrenochrome hypothesis of schizophrenia revisited". Neurotoxicity Research 4 (2): 147–150. doi:10.1080/10298420290015827.
- ^ "The controversy that these reports created just sort of died away, and the adrenochrome family has never been accepted as being psychedelic. No one in the scientific community today is looking in and about the area, and at present this is considered as an interesting historical footnote." As seen at: Alexander Shulgin and Ann Shulgin (1991). "#157 (TMA)". PiHKAL - A Chemical Love Story. Transform Press.
- ^ Hoffer, A. Osmond, H., Smithies, J.; Schizophrenia: a new approach. Journal of Mental Science #100 (January, 1954)
- ^ Hoffer, A (Q1 1990). "The Adrenochrome Hypothesis and Psychiatry". Retrieved 2011-07-25.
- ^ Hoffer, A. and Osmond, H. The Hallucinogens (Academic Press, 1967).
- ^ Hoffer, A., Osmond, H., & Smythies, J. (1994). An Evolutionary Defense Against Severe Stress. Schizophrenia: A New Approach (pp. 205-221). Victoria, Canada: Journal of Orthomolecular Medicine
- ^ Erowid. "Adrenochrome Law". Retrieved 2013-01-14.
- ^ Thompson, Hunter S. (1971). Fear and Loathing in Las Vegas. Random House. ISBN 0-679-78589-2.
- ^ http://www.pbs.org/wgbh/masterpiece/lewis/destroy_synopsis.html
External links
- Adrenochrome Commentary at erowid.org
- Adrenochrome deposits resulting from the use of epinephrine-containing eye drops used to treat glaucoma from the Iowa Eye Atlas (searched for diagnosis = adrenochrome)
English Journal
- Response of Vibrio cholerae to the Catecholamine Hormones Epinephrine and Norepinephrine.
- Halang P1, Toulouse C1, Geißel B1, Michel B1, Flauger B2, Müller M3, Voegele RT3, Stefanski V2, Steuber J4.
- Journal of bacteriology.J Bacteriol.2015 Dec 15;197(24):3769-78. doi: 10.1128/JB.00345-15. Epub 2015 Sep 28.
- In Escherichia coli or Salmonella enterica, the stress-associated mammalian hormones epinephrine (E) and norepinephrine (NE) trigger a signaling cascade by interacting with the QseC sensor protein. Here we show that Vibrio cholerae, the causative agent of cholera, exhibits a specific response to E a
- PMID 26416829
- In cellulo monitoring of quinone reductase activity and reactive oxygen species production during the redox cycling of 1,2 and 1,4 quinones.
- Cassagnes LE1, Perio P1, Ferry G2, Moulharat N2, Antoine M2, Gayon R3, Boutin JA2, Nepveu F1, Reybier K4.
- Free radical biology & medicine.Free Radic Biol Med.2015 Dec;89:126-34. doi: 10.1016/j.freeradbiomed.2015.07.150. Epub 2015 Sep 18.
- Quinones are highly reactive molecules that readily undergo either one- or two-electron reduction. One-electron reduction of quinones or their derivatives by enzymes such as cytochrome P450 reductase or other flavoproteins generates unstable semiquinones, which undergo redox cycling in the presence
- PMID 26386287
- A high-throughput adrenaline test for the exploration of the catalytic potential of halohydrin dehalogenases in epoxide ring-opening reactions.
- Tang L1, Liu Y1, Jiang R1, Zheng Y1, Zheng K1, Zheng H1.
- Biotechnology and applied biochemistry.Biotechnol Appl Biochem.2015 Jul-Aug;62(4):451-7. doi: 10.1002/bab.1278. Epub 2015 Jul 26.
- The principle of the adrenaline test for enzymes is based on the quantification of periodate-sensitive reaction products with adrenaline to produce a chromogenic compound adrenochrome that can be easily detected. Here, a rapid whole-cell -based adrenaline assay for the activity measurement of halohy
- PMID 25099782
Japanese Journal
- Involvement of carbonyl reductase in superoxide formation through redox cycling of adrenochrome and 9,10-phenanthrenequinone in pig heart
- Oginuma Michiko,Shimada Hideaki,Imamura Yorishige,オギヌマ ミチコ,シマダ ヒデアキ,イマムラ ヨリシゲ,荻沼 道子,島田 秀昭,今村 順茂
- Chemico-Biological Interactions 155(3), 148-154, 2005-08-15
- … The effects of adrenochrome, a metabolite of epinephrine (adrenaline), and 9,10-phenanthrenequinone (PQ), a component of diesel exhaust particles, on the stereoselective reduction of 4-benzoylpyridine (4-BP) were examined in pig heart cytosol. … PQ was a potent inhibitor for the 4-BP reduction, while adrenochrome was a poor inhibitor. … A similar result was observed in the effects of adrenochrome and PQ on the reduction of all-trans retinal. …
- NAID 120005254874
- 塩酸エピネフリン水溶液の自動酸化に対するガングリオシドGM1ミセルの影響
Related Links
- A supplier of quality personel and cutting edge technology and techniques to the film and television industry. Adrenochrome Productions is driven primarily by its owner Martin Stacey who first began working in the industry in 1994.
- Adrenochrome. 56 likes. "but beefsteak is delicious!" ... Highlights Highlights Posts by Page Posts by Others Adrenochrome September 7, 2012 Hey. So without dwelling into the specifics, we've all mutually decided to end ...
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