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词条 Adrenochrome
释义

  1. Chemistry

  2. Effect on the brain

  3. Law

  4. In popular culture

  5. References

  6. External links

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477243063
| Name = Adrenochrome
| ImageFile = Adrenochrom.svg
| ImageSize = 170
| ImageAlt = Structural formula of adrenochrome
| ImageFile1 = Adrenochrome 3D ball.png
| ImageSize1 = 170
| ImageAlt1 = Ball-and-stick model of the adrenochrome molecule
| IUPACName = 3-Hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione
| OtherNames = Adraxone; Pink adrenaline
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5687
| InChI = 1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
| InChIKey = RPHLQSHHTJORHI-UHFFFAOYAD
| PubChem = 5898
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RPHLQSHHTJORHI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 54-06-8
| SMILES = O=C1\\C=C2/C(=C\\C1=O)N(CC2O)C
}}
| Section2 = {{Chembox Properties
| C=9|H=9|N=1|O=3
| Density = 3.264 g/cm3
| BoilingPtC = 115-120
| BoilingPt_notes = (decomposes)
}}

Adrenochrome is a chemical compound with the molecular formula C9H9NO3 produced by the oxidation of adrenaline (epinephrine). The derivative carbazochrome is a hemostatic medication. Despite a similarity in chemical names, it is unrelated to chrome or chromium.

Chemistry

In vivo, adrenochrome is synthesized by the oxidation of epinephrine. In vitro, silver oxide (Ag2O) is used as an oxidizing agent.[1] 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) conducted in the 1950s and 1960s reported that adrenochrome triggered psychotic reactions such as thought disorder, derealization, and euphoria.[2] 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.[3] In what they called the "adrenochrome hypothesis",[4] they speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome.[5][6] While the treatment of schizophrenia with such potent anti-oxidants is highly contested in the literature, and adrenochrome is not currently believed to have any psychedelic properties,[7] a number of recently published papers consider Hoffer's paper a landmark contribution to the notion that impairment of what's now termed the anti-oxidant defense system (AODS) seems to play a role in schizophrenia.[8]

Law

Adrenochrome is unscheduled by the Controlled Substances Act in the United States, but 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]{{unreliable source?|date=March 2015}}

In popular culture

  • Author Hunter S. Thompson mentioned adrenochrome in his book Fear and Loathing in Las Vegas. 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. Hunter S. Thompson also mentions adrenochrome in his book Fear and Loathing on the Campaign Trail '72. In the footnotes in chapter April, page 140 he says, "It was sometime after midnight in a ratty hotel room and my memory of the conversation is haze, due to massive ingestion of booze, fatback, and forty cc's of adrenochrome."
  • The harvesting of an adrenal gland from a live victim to obtain adrenochrome for drug abuse is a plot feature in the first episode "Whom the Gods would Destroy", of Series 1 of the British TV series Lewis (2008).[10]
  • In Anthony Burgess' 1962 novel A Clockwork Orange, "drencrom" (presumably the Nadsat term for adrenochrome) is listed as one of the potential drugs that can be added to milk-plus (milk laced with a drug of the consumer's choice).

The 1980's goth band The Sisters of Mercy had a song called Andrenochrome.

References

1. ^MacCarthy, Chim, Ind. Paris 55,435(1946)
2. ^{{cite journal | vauthors = Smythies J | title = The adrenochrome hypothesis of schizophrenia revisited | journal = Neurotoxicity Research | volume = 4 | issue = 2 | pages = 147–50 | date = March 2002 | pmid = 12829415 | doi = 10.1080/10298420290015827 | citeseerx = 10.1.1.688.3796 }}
3. ^{{cite journal | vauthors = Hoffer A, Osmond H, Smithies J | title = Schizophrenia; a new approach. II. Result of a year's research | journal = The Journal of Mental Science | volume = 100 | issue = 418 | pages = 29–45 | date = January 1954 | pmid = 13152519 | doi = 10.1192/bjp.100.418.29| url = }}
4. ^{{cite journal | vauthors = Hoffer A | title = The Adrenochrome Hypothesis and Psychiatry | journal = The Journal of Orthomolecular Medicine | volume = 14 | issue = 1 | year = 1999 | pages = 49–62 | url = http://www.orthomolecular.org/library/jom/1999/articles/1999-v14n01-p049.shtml }}
5. ^{{cite book| vauthors = Hoffer A, Osmond H | title = The Hallucinogens | publisher = Academic Press | date = 1967 |isbn=978-1-4832-6169-0 }}
6. ^{{cite journal | vauthors = Hoffer A | date = 1994 | title = Schizophrenia: An Evolutionary Defense Against Severe Stress | journal = Journal of Orthomolecular Medicine | volume = 9 | issue = 4 | pages = 205–221 | url = http://orthomolecular.org/library/jom/1994/pdf/1994-v09n04-p205.pdf }}
7. ^"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: {{cite book|title=PiHKAL - A Chemical Love Story | vauthors = Shulgin A, Shulgin A | author-link1 = Alexander Shulgin | author-link2 = Ann Shulgin |chapter=#157 (TMA) |url=http://www.erowid.org/library/books_online/pihkal/pihkal157.shtml |publisher= Transform Press |year=1991 }}
8. ^{{cite journal | vauthors = Yao JK, Reddy R | title = Oxidative stress in schizophrenia: pathogenetic and therapeutic implications | journal = Antioxidants & Redox Signaling | volume = 15 | issue = 7 | pages = 1999–2002 | date = October 2011 | pmid = 21194354 | pmc = 3159103 | doi = 10.1089/ars.2010.3646 }}
9. ^{{cite web | last = Erowid | title = Adrenochrome Law | url = http://www.erowid.org/chemicals/adrenochrome/adrenochrome_law.shtml | access-date= 2013-01-14 }}
10. ^{{cite web | url=https://www.pbs.org/wgbh/masterpiece/lewis/destroy_synopsis.html | title=Inspector Lewis Series Synopsis | archive-url=https://web.archive.org/web/20080626133403/http://www.pbs.org/wgbh/masterpiece/lewis/destroy_synopsis.html | archive-date=2008-06-26}}

External links

  • Adrenochrome Commentary at erowid.org
  • [https://web.archive.org/web/20090111090507/http://webeye.ophth.uiowa.edu/eyeforum/atlassearch1.htm?ComparisonType1_1=LIKE&Value1_1=adrenochrome&FieldName1=Diagnosis&NumCriteriaDetails1=1&PageID=2&GlobalOperator=AND&NumCriteria=1 Adrenochrome deposits] resulting from the use of epinephrine-containing eye drops used to treat glaucoma from the [https://web.archive.org/web/20050303205443/http://webeye.ophth.uiowa.edu/eyeforum/atlassearch1.htm Iowa Eye Atlas] (searched for diagnosis = adrenochrome)

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