Adrenochrome

Structural formula
	Structural formula without stereochemistry
General
Surname	Adrenochrome
other names	Adraxon; 3-hydroxy-1-methyl-2,3-dihydro-1 H -indole-5,6-dione; 3-hydroxy-1-methyl-5,6-indolinedione;
Molecular formula	C 9 H 9 NO 3
Brief description	red crystals
External identifiers / databases
EC number	200-192-8
ECHA InfoCard	100,000.176
PubChem	5898
ChemSpider	5687
Wikidata	Q366835
properties
Molar mass	179.17 g · mol -1
Physical state	firmly
Melting point	125 ° C
solubility	soluble in water and ethanol
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	128 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Adrenochrome is a metabolic product of adrenaline and is involved in the formation of skin pigment ( melanocytes ). It was examined more closely in 1952 in the course of clinical studies to understand schizophrenia and its treatment. It belongs to the chemical group of aminochromes and is related to adrenolutin , which has similar properties.

history

In the early 1950s, research was conducted into various means of treating mental illness. A. Hoffer and H. Osmond presented a. a. the hypothesis that the body's own adrenochrome, which was discovered in the 1940s, inspires the “imagination” of schizophrenic personalities and thus makes a decisive contribution to the clinical picture. They called this hypothesis the adrenochrome hypothesis.

The hallucinogenic effects of adrenochrome were discovered in the course of her studies on the intervention in the body's own adrenochrome household to treat schizophrenic personalities . These effects seemed very similar to those of LSD and mescaline , if not as potent. Hoffer and Osmond then put forward the hypothesis that LSD and mescaline would stimulate the body's own production of adrenochrome and are therefore responsible for its hallucinogenic effects. They described their studies on the hallucinogenic effects in 1967 in their joint specialist book "The Hallucinogens".

The adrenochrome hypothesis was further developed into the aminochrome hypothesis and, in the opinion of Hoffer and Osmond, best described the biochemical processes in the development of schizophrenia; Cadet and Lohr also came to the same conclusion in 1987.

Formation and dismantling

Adrenochrome is produced both in small quantities in the human body and in the air through the oxidation of adrenaline. The formation in the body takes place through superoxide anions and can be prevented by the enzyme superoxide dismutase . In the air, the adrenochrome breaks down very quickly into other substances if it is not stored appropriately. In the body, the enzyme glutathione S-transferase conjugates it with glutathione and breaks it down.

Long-term treatment with eye drops containing adrenaline can lead to dark deposits of adrenochrome in the cornea .

Manufacturing

Adrenochrome can be obtained by oxidizing adrenaline with silver (I) oxide (Ag ₂ O).

In addition, adrenaline can also be oxidized to adrenochrome with CTADC (cetyltrimethylammonium dichromate).

Popular culture

By resorting to the outdated misjudgment of the substance as psychoactive, Adrenochrom gained a certain public fame through the book Fear and Loathing in Las Vegas by Hunter S. Thompson and its filming, as well as through the song Adrenochrome by the British band The Sisters of Mercy , published on the B - Page of the Body-Electric EP from 1982.

The substance also plays a role as a drug in demons of the past in the crime series Lewis - Der Oxford Krimi and in the Hollywood thriller From Hell .

Adrenochrome is also part of a number of contemporary conspiracy theories such as QAnon and Pizzagate . These theories claim the existence of underground camps where the substance is tapped from children.

In 2020 the Antilopen Gang will release an album titled Adrenochrom.

Web links

Adrenochrome . In: Erowid . (English)

Individual evidence

↑ ^a ^b Entry on adrenochrome. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
↑ ^a ^b Entry on adrenochrome in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Adrenochrome data sheet from Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).

^ A. Hoffer, H. Osmond: The Adrenochrome Hypothesis an Psychiatry. In: Journal of Orthomolecular Medicine , Vol. 5, No. 1, 1990.

↑ Savov VM, Eluashvili IA, Pisarev VA, Prilipko LL, Kagan VE: NADPH2 and organic hydroperoxide-dependent oxidation of adrenaline to adrenochromes in liver and brain microsomes . In: Biull Eksp Biol Med . 90, No. 11, November 1980, pp. 555-7. PMID 6256023 .

↑ Baez S, Segura-Aguilar J, Widersten M, Johansson AS, Mannervik B: Glutathione transferases catalyze the detoxication of oxidized metabolites (o-quinones) of catecholamines and may serve as an antioxidant system preventing degenerative cellular processes . In: Biochem. J. . 324 (Pt 1), May 1997, pp. 25-8. PMID 9164836 . PMC 1218396 (free full text).

↑ Sarita Garnayak, Sabita Patel: Oxidation of Epinephrine to Adrenochrome by Cetyltrimethylammonium Dichromate: A Mechanistic Study . In: Industrial & Engineering Chemistry Research . tape 53 , no. 31 , 23 July 2014, ISSN 0888-5885 , p. 12249–12256 , doi : 10.1021 / ie500037x ( acs.org [PDF; accessed April 8, 2020]).

↑ Alex Nichols: Slender Man for Boomers . June 6, 2019. Retrieved April 2, 2020.

↑ Ralf Nowotny: Adrenochrome - The alleged rejuvenation drug of the "Hollywood elite" . April 7, 2020.

↑ Manfred Dworschak: QAnon Movement: Why the belief in conspiracies is so popular. In: Spiegel Online . July 17, 2020, accessed July 23, 2020 .

↑ Christian Röther: Conspiracy myths - the movement "QAnon" becomes a religion. In: deutschlandfunk.de. June 10, 2020, accessed July 23, 2020 .

[Römpp-1] Entry on adrenochrome. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.

[ChemIDplus-2] Entry on adrenochrome in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-3] Adrenochrome data sheet from Sigma-Aldrich , accessed on June 14, 2011 ( PDF ).

[4] A. Hoffer, H. Osmond: The Adrenochrome Hypothesis an Psychiatry. In: Journal of Orthomolecular Medicine , Vol. 5, No. 1, 1990.

[5] Savov VM, Eluashvili IA, Pisarev VA, Prilipko LL, Kagan VE: NADPH2 and organic hydroperoxide-dependent oxidation of adrenaline to adrenochromes in liver and brain microsomes . In: Biull Eksp Biol Med . 90, No. 11, November 1980, pp. 555-7. PMID 6256023 .

[6] Baez S, Segura-Aguilar J, Widersten M, Johansson AS, Mannervik B: Glutathione transferases catalyze the detoxication of oxidized metabolites (o-quinones) of catecholamines and may serve as an antioxidant system preventing degenerative cellular processes . In: Biochem. J. . 324 (Pt 1), May 1997, pp. 25-8. PMID 9164836 . PMC 1218396 (free full text).

[7] Sarita Garnayak, Sabita Patel: Oxidation of Epinephrine to Adrenochrome by Cetyltrimethylammonium Dichromate: A Mechanistic Study . In: Industrial & Engineering Chemistry Research . tape 53 , no. 31 , 23 July 2014, ISSN 0888-5885 , p. 12249–12256 , doi : 10.1021 / ie500037x ( acs.org [PDF; accessed April 8, 2020]).

[8] Alex Nichols: Slender Man for Boomers . June 6, 2019. Retrieved April 2, 2020.

[9] Ralf Nowotny: Adrenochrome - The alleged rejuvenation drug of the "Hollywood elite" . April 7, 2020.

[SPON-000172071858-10] Manfred Dworschak: QAnon Movement: Why the belief in conspiracies is so popular. In: Spiegel Online . July 17, 2020, accessed July 23, 2020 .

[deutschl-478337-11] Christian Röther: Conspiracy myths - the movement "QAnon" becomes a religion. In: deutschlandfunk.de. June 10, 2020, accessed July 23, 2020 .