Adrenochrome
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MedKoo CAT#: 591210

CAS#: 54-06-8

Description: Adrenochrome, also known as adraxone, is a stable oxidation product formed after oxidation of adrenaline. Adrenochrome strongly stimulates oxygen uptake occurring during the autoxidation of adrenaline, other catecholamines and ascorbate. The reduction of adrenochrome operated by adrenaline is accelerated by the exclusion of oxygen indicating that the oxidation of adrenaline occurs directly and superoxide anion does not necessarily mediate it. Adrenochrome was the subject of limited research from the 1950s through to the 1970s as a potential cause of schizophrenia. While it has no current medical application, the related derivative compound, carbazochrome, is a hemostatic medication.

Chemical Structure

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Adrenochrome
CAS# 54-06-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 591210
Name: Adrenochrome
CAS#: 54-06-8
Chemical Formula: C9H9NO3
Exact Mass: 179.06
Molecular Weight: 179.180
Elemental Analysis: C, 60.33; H, 5.06; N, 7.82; O, 26.79

Price and Availability

Size Price Availability Quantity
10mg USD 90 Ready to ship
25mg USD 165 Ready to ship
50mg USD 285 Ready to ship
100mg USD 495 Ready to ship
200mg USD 825 Ready to ship
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Synonym: Adraxone; Adrenochrome;

IUPAC/Chemical Name: 3-Hydroxy-1-methylindoline-5,6-dione

InChi Key: RPHLQSHHTJORHI-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3

SMILES Code: O=C1C=C2C(O)CN(C)C2=CC1=O

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Adrenochrome is an oxidation product of Epinephrine. Adrenochrome is a potent coronary constricting agent in the rat heart. Adrenochrome can be used for neurological disorder research.
In vitro activity: This study found that in cultured human umbilical arterial endothelial cells, adrenochrome inhibited [3H]thymidine incorporation, decreased protein content, stimulated [3H]cholesterol uptake, and decreased prostacyclin production after 3, 5, 24 and 5 hrs of 200 microM, respectively, compared with control. Reference: Res Commun Mol Pathol Pharmacol. 1995 Jul;89(1):111-26. https://pubmed.ncbi.nlm.nih.gov/7582857/
In vivo activity: Phenanthrenequinone mediated efficiently the formation of superoxide anion radical through its redox cycling in pig heart cytosol, adrenochrome had no ability to mediate the superoxide formation. These may be because the reactivity for adrenochrome, catalyzed by pig heart carbonyl reductase, is much lower than that for phenanthrenequinone. Reference: Chem Biol Interact. 2005 Aug 15;155(3):148-54. https://pubmed.ncbi.nlm.nih.gov/16026774/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 558.10

Preparing Stock Solutions

The following data is based on the product molecular weight 179.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Moreau V, Novak MJ, Moore LK. Effect of adrenalin, adrenochrome, and adrenolutin on connexin proteins in the cardiovasculature. Toxicol Mech Methods. 2006;16(7):373-7. doi: 10.1080/15376520600632039. PMID: 20021010. 2. Zhou Q, Hulea S, Kummerow FA. Effects of adrenochrome and epinephrine on human arterial endothelial cells in vitro. Res Commun Mol Pathol Pharmacol. 1995 Jul;89(1):111-26. PMID: 7582857. 3. Oginuma M, Shimada H, Imamura Y. Involvement of carbonyl reductase in superoxide formation through redox cycling of adrenochrome and 9,10-phenanthrenequinone in pig heart. Chem Biol Interact. 2005 Aug 15;155(3):148-54. doi: 10.1016/j.cbi.2005.06.002. PMID: 16026774. 4. Moreau V, Novak MJ, Moore LK. Effect of adrenalin, adrenochrome, and adrenolutin on connexin proteins in the cardiovasculature. Toxicol Mech Methods. 2006;16(7):373-7. doi: 10.1080/15376520600632039. PMID: 20021010.
In vitro protocol: 1. Moreau V, Novak MJ, Moore LK. Effect of adrenalin, adrenochrome, and adrenolutin on connexin proteins in the cardiovasculature. Toxicol Mech Methods. 2006;16(7):373-7. doi: 10.1080/15376520600632039. PMID: 20021010. 2. Zhou Q, Hulea S, Kummerow FA. Effects of adrenochrome and epinephrine on human arterial endothelial cells in vitro. Res Commun Mol Pathol Pharmacol. 1995 Jul;89(1):111-26. PMID: 7582857.
In vivo protocol: 1. Oginuma M, Shimada H, Imamura Y. Involvement of carbonyl reductase in superoxide formation through redox cycling of adrenochrome and 9,10-phenanthrenequinone in pig heart. Chem Biol Interact. 2005 Aug 15;155(3):148-54. doi: 10.1016/j.cbi.2005.06.002. PMID: 16026774. 2. Moreau V, Novak MJ, Moore LK. Effect of adrenalin, adrenochrome, and adrenolutin on connexin proteins in the cardiovasculature. Toxicol Mech Methods. 2006;16(7):373-7. doi: 10.1080/15376520600632039. PMID: 20021010.

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1: Cassagnes LE, Chhour M, Pério P, Sudor J, Gayon R, Ferry G, Boutin JA, Nepveu F, Reybier K. Oxidative stress and neurodegeneration: The possible contribution of quinone reductase 2. Free Radic Biol Med. 2018 May 20;120:56-61. doi: 10.1016/j.freeradbiomed.2018.03.002. Epub 2018 Mar 8. PubMed PMID: 29526807.

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12: Miller CL. The chemical interaction between adrenochrome, three different classes of antipsychotic drugs and metabolites of the kynurenine pathway. Eur Neuropsychopharmacol. 2015 Mar;25(3):435-40. doi: 10.1016/j.euroneuro.2014.12.001. Epub 2014 Dec 18. PubMed PMID: 25554565.

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14: Oh-oka H, Yamada T, Noto H, Umeyama T, Kadekawa K, Ashitomi K, Nishijima S, Sugaya K. Effect of carbazochrome sodium sulfonate on refractory chronic prostatitis. Int J Urol. 2014 Nov;21(11):1162-6. doi: 10.1111/iju.12533. Epub 2014 Jun 25. PubMed PMID: 24964194.

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20: Nishijima S, Sugaya K, Kadekawa K, Ashitomi K, Ueda T, Yamamoto H. High-dose tranilast administration to rats creates interstitial cystitis-like symptoms with increased vascular permeability. Life Sci. 2013 Nov 26;93(23):897-903. doi: 10.1016/j.lfs.2013.10.010. Epub 2013 Oct 21. PubMed PMID: 24157455.