Adrenochrome: Difference between revisions
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! {{chembox header}}| '''Adrenochrome''' <!-- replace if not identical with the article name --> |
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:adrenochrome-Line- |
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:adrenochrome-Line-Structure2.png|200px|Adrenochrome]] <!-- replace if not identical with the pagename --> |
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:adrenochrome-Space-filling.png|200px|Adrenochrome]] <!-- replace if not identical with the pagename --> |
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:adrenochrome-Ball-and-Stick-Animation.gif|200px|Adrenochrome]] <!-- replace if not identical with the pagename --> |
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| [[IUPAC nomenclature|Systematic name]] |
| [[IUPAC nomenclature|Systematic name]] |
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| 3-hydroxy-1-methyl |
| 2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dione |
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| [[Chemical formula]] |
| [[Chemical formula]] |
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| x.xxx g/cm³ |
| x.xxx g/cm³ |
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| [[Melting point]] |
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| xx.x °C |
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| [[Boiling point]] |
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| (decomposes, 115-120 °C) |
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| [[CAS registry number|CAS number]] |
| [[CAS registry number|CAS number]] |
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| [54-06-8] |
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| [[Simplified molecular input line entry specification|SMILES]] |
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'''Adrenochrome''', chemical formula [[carbon|C]]<sub>9</sub>[[hydrogen|H]]<sub>9</sub>[[nitrogen|N]][[oxygen|O]]<sub>3</sub>, is |
'''Adrenochrome''', chemical formula [[carbon|C]]<sub>9</sub>[[hydrogen|H]]<sub>9</sub>[[nitrogen|N]][[oxygen|O]]<sub>3</sub>, is a [[pigment]] obtained by the [[oxidation]] of [[adrenaline]] ( [[epinephrine]] ) . '''Adrenochrome monosemicarbazone''', also known as '''carbazochrome''', is a [[hemostatic]]. |
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it reduces capillary bleeding. |
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== Schizophrenia hypothesis == |
== Schizophrenia hypothesis == |
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== Chemistry == |
== Chemistry == |
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Adrenochrome is synthesized in vivo by the oxidation of epinephrine. |
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An adrenochrome solution would likely be synthesized by a process involving suspension of adrenaline in an aqueous solution (likely water to suspend and trace [[HCl]] to dissolve). [[Silver oxide]] or [[catechol oxidase]] would be added for the requisite [[oxidation]] process, and the solution filtered to remove the adrenochrome. |
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In vitro, Ag2O is used as an oxidizing agent (MacCarthy, Chim, Ind. Paris 55,435(1946)) |
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optimum pH of water solution = 4 |
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== Psychedelic use == |
== Psychedelic use == |
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== References == |
== References == |
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<references/> |
<references/> |
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== External links == |
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* [http://www.erowid.org/chemicals/adrenochrome/adrenochrome.shtml Erowid adrenochrome vault] |
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{{ChemicalSources}} |
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[[Category:Alcohols]] |
[[Category:Alcohols]] |
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Revision as of 04:17, 21 November 2006
| Adrenochrome | ||
|---|---|---|
| Adrenochrome | ||
| Systematic name | 2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dione | |
| Chemical formula | C9H9NO3 | |
| Molecular mass | 179.175 g/mol | |
| Density | x.xxx g/cm³ | |
| Boiling point | (decomposes, 115-120 °C) | |
| CAS number | [54-06-8] | |
| SMILES | O=C1C=C2C(O)CN(C)C2=CC1=O | |
| Disclaimer and references | ||
Adrenochrome, chemical formula C9H9NO3, is a pigment obtained by the oxidation of adrenaline ( epinephrine ) . Adrenochrome monosemicarbazone, also known as carbazochrome, is a hemostatic. it reduces capillary bleeding.
Schizophrenia hypothesis
Studies in the mid-twentieth century have indicated that adrenochrome is metabolized as one of two other substances, dihydroxyindole or adrenolutin. Dihydroxyindole may balance the anxiety and depression effects of adrenaline to reduce tension and irritability. Defective processing of adrenochrome, however, primarily produces the toxic adrenolutin instead, which combines with adrenochrome. The adrenochrome-adrenolutin combination is hypothesized by Dr. Abram Hoffer and Humphry Osmond to result in disruption of the brain's normal chemical processes. This disruption, according to their hypothesis, would be responsible for the symptomatology of schizophrenia. This hypothesis has long been opposed by proponents of the establishment medical industry.
Chemistry
Adrenochrome is synthesized in vivo by the oxidation of epinephrine. In vitro, Ag2O is used as an oxidizing agent (MacCarthy, Chim, Ind. Paris 55,435(1946)) optimum pH of water solution = 4
Psychedelic use
There has been a substantial amount of controversy about whether adrenochrome can be classified as a hallucinogenic drug. Even though adrenochrome induces remarkable psychoactive effects, most researchers agree that an adrenochrome experience does not qualify as a psychedelic one. Psychoactive effects of adrenochrome include euphoria, confusion, changed train of thought, lack of judgment, poor insight and inability to concentrate.[1] In one study[2], test subjects compared adrenochrome experience to mild psilocybin and LSD experiences.
Fear and Loathing in Las Vegas
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 (removing the gland kills the donor; it cannot be taken from 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". 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 fictional hyperbole.
The Sisters Of Mercy
The Sisters Of Mercy's second single Body Electric has a song called Adrenochrome on the B-side, the lyrics of which contain apparent references to the drug's psychedelic effect: High tide / Wide eyed / Sped on adrenochrome
A Clockwork Orange
In the book and film A Clockwork Orange, the presence of a drug whose street name is "drencrom" is possibly a reference to adrenochrome.