04-19-00 07:12
No 122785
the Hive BB
Serious Chemistry Forum
Oxidative mechanism of epinephrine -> andrenochrome
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Author Topic: Oxidative mechanism of epinephrine -> andrenochrome
rev drone
Hive Bee posted 01-24-1999 06:02 PM
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Anybody who's read "Fear and Loathing in Las Vegas" with their eyes open has wondered about that andrenochrome scene. What is that stuff? Where do I get that stuff? etc.
Well, andrenochrome is 3-hydroxy-1-methyl-5,6-indoline-dione -- made by the oxidation of epinephrine (andrenalin). Now I can see where the hydrogens were abstracted from, and I can generally speculate about the mechnism, but does anyone have the definative word on electron-pushing for this little chemical anomaly?
Also, does anyone have experience with this stuff? Johnny Depp sure made it look kewl, and being the young, impressionable lad that I am, I'd sure like to know if it is "all that" or not.
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-the good reverend drone
Later papers where negative results or possible slight effects were obtained by dosages up to 25mg: I believe that the ultimate athority of Shulgin refered to adrenochrome as "a facinating red herring" in Tihkal. And I really hate to argue with Him. I believe that the original, positive reports were based on experiments with one mentally unstable woman. This was covered in Hoffer and Osmonds The Hallucinogens, I believe. Other reviews are : Opinions that adrenochrome is not active: In Nature 191, 245, ’61 it was pointed out that adrenochrome may have significance as a hallucinogen, since it is an in vitro glutamic acid decarboxylase and cholinesterase inhibitor. It has also been described as having a wide range of other physiological activites, as reviewed in Of course, most of this work was done under conditions that would be considered primitive today, and there is not absolute certainty that all research groups were working with the same compound. Originally, adrenochrome was prepared by oxidation of adrenalin with catechol oxidase or silver oxide. The chemistry of its preparation is reviewed in Chem. Rev. 59, 181, ’59. Additionally, adrenochrome semicarbazone has been claimed to have hallucinogenic properties similar to the parent substance: Acta Chem. Scand. 12, 1231, ’58. It certainly would be interesting to apply modern techniques to this mystery and settle it once and for all. Anyone looking for a research project? Reaction ID 352748 Reaction Details 1 of 7 Reaction Classification Preparation Reaction Details 2 of 7 Reaction Classification Preparation Reaction Details 3 of 7 Reaction Classification Preparation Reaction Details 4 of 7 Reaction Classification Preparation Reaction Details 5 of 7 Reaction Classification Preparation Reaction Details 6 of 7 Reaction Classification Preparation Reaction Details 7 of 7 Reaction Classification Preparation Reaction Reaction ID 2106910 Reaction Details 1 of 2 Reaction Classification Chemical behaviour Reaction Details 2 of 2 Reaction Classification Chemical behaviour Reaction ID 2106911 Reaction Details Reaction Classification Chemical behaviour Reaction ID 2106912 Reaction Details Reaction Classification Chemical behaviour Reaction Reaction ID 2173865 Reaction Details Reaction Classification Chemical behaviour Reaction Reaction ID 2199350 Reaction Details Reaction Classification Preparation Reaction Reaction ID 3658966 Reaction Details Reaction Classification Chemical behaviour ------------------ I had no idea that this was still a current topic of research, but there were over 100 cites, just going back to 1986. [Chemical interaction between serotonin and adrenochrome. Contribution to the "short circuit" theory of the genesis of mental disease] Short circuit theory on the onset of mental illness. Usage: 100 mg is thoroughly dissolved in just enough alcohol, melted fat (butter), or vegetable oil and ingested. Because of its poor solubility in water these must be used to aid absorption. Effects: Physical stimulation, feeling of well-being, slight reduction of thought processes. Contraindications: None noted. Act as a systemic hemostatic preventing capilary bleeding during injury. Adrenochrome causes chemicaly induced schizophrenia. Its semicarbazone does not... ------------------ Contact Us | the Hive Powered by: Ultimate Bulletin Board, Version 5.43c
Beagle
Hive Bee posted 01-25-1999 09:36 AM
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I have no experience with this compound, but of course I am very interested in it. Here are the original refs, in case anyone is willing to follow up on it.
The original paper, in which Hoffer obtained "profound psychomimetic symptoms" from as little as 0.5 mg S.C. or I.V.:
J. Mental Sci. 100, 29, '54
Am. J. Psychiat. 111, 603, '55
ibid 115, 162, '58
ibid 116, 454, '59
Lancet ii, 308, '58
Hormones, Brain Function and Behavior, p181 1957.
Psychotropic Drugs p.10, 1957
Lancet, I 1287, 1960.
Pharmacol. Rev. 1, 1, ’49
Fortschr. Chem. Org. Naturstoffe. 14, 217, ’57
rev drone
Hive Bee posted 01-25-1999 10:04 AM
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Many thanks for the extensive foray into andrenochrome you've offered. I have a few more andrenalin oxidations I can offer. I was told epinephrine was available OTC in a veterinary context, but otherwise is avaiable in bulk through several chemical companies. THe synthesis is a mere one-step reaction, so it looks like the makings of a fun weekend project. Off to the library I go...
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-the good reverend drone
Beagle
Hive Bee posted 01-25-1999 11:00 AM
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I would be glad to hear of any other epinephrine oxidations that you could offer.
Also, for another fun fictionalized account of adrenochrome in the vein of H.S. Thompson, see Blood of a Wig, from the book Red Dirt Marijuana and Other Stories, by Terry Southern.
rev drone
Hive Bee posted 01-25-1999 01:06 PM
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The folowing were taken from Beilstein
Reaction
Reactant BRN 2368277 4-((R)-1-hydroxy-2-methylamino-ethyl)-be
Product BRN 84667 (R)-3-hydroxy-1-methyl-indoline-5,6-dion
-------------------------
Reagent silver oxide
methanol
Ref. 1 1053607; Journal; Ellis; JPETAB; J.Pharmacol.Exp.Ther.; 79; 1943; 364,368;
Ref. 2 1053608; Journal; Veer; RTCPA3; Recl.Trav.Chim.Pays-Bas; 61; 1942; 638,643;
-------------------------
Reagent silver oxide
ethanol
Ref. 1 1053607; Journal; Ellis; JPETAB; J.Pharmacol.Exp.Ther.; 79; 1943; 364,368;
Ref. 2 1053608; Journal; Veer; RTCPA3; Recl.Trav.Chim.Pays-Bas; 61; 1942; 638,643;
-------------------------
Reagent silver oxide
methanol
formic acid
Ref. 1 1053583; Journal; Heacock et al.; CJCHAG; Can.J.Chem.; 36; 1958; 853,855;
Ref. 2 1053605; Journal; Sobotka; Austin; JACSAT; J.Amer.Chem.Soc.; 73; 1951; 3077;
Ref. 3 1053598; Journal; Harley-Mason; JCSOA9; J.Chem.Soc.; 1950; 1276,1279;
Ref. 4 1053586; Journal; Ingle et al.; JPHAA3; J.Am.Pharm.Assoc.; 37; 1948; 375;
Ref. 5 1053606; Journal; MacCarthy; CHIEAN; Chim.Ind.(Paris); 55; 1946; 435;
-------------------------
Reagent oxygen
Other conditions in Gegenwart von Katalysatoren
Ref. 1 1053600; Journal; Green et al.; JBCHA3; J.Biol.Chem.; 220; 1956; 237;
Ref. 2 1053601; Journal; Chaix et al.; BBACAQ; Biochim.Biophys.Acta; 5; 1950; 472,473;
Ref. 3 1053602; Journal; Drevon; Stupfel; C.r.Soc.Biol.; 143; 1949; 271;
Ref. 4 1053603; Journal; Blaschko; Schlossmann; J.Physiol.London; 98; 1940; 130-140;
Ref. 5 1053604; Journal; Green; Richter; BIJOAK; Biochem.J.; 31; 1937; 598,609;
-------------------------
Reagent iron (2+)
hydrogen peroxide
Ref. 1 1053598; Journal; Harley-Mason; JCSOA9; J.Chem.Soc.; 1950; 1276,1279;
Ref. 2 1053599; Journal; Mazur et al.; JBCHA3; J.Biol.Chem.; 220; 1956; 227;
-------------------------
Reagent iron (2+)
sodium peroxo disulfate
Ref. 1 1053598; Journal; Harley-Mason; JCSOA9; J.Chem.Soc.; 1950; 1276,1279;
Ref. 2 1053599; Journal; Mazur et al.; JBCHA3; J.Biol.Chem.; 220; 1956; 227;
-------------------------
Reagent water
iodic acid
Ref. 1 1053597; Journal; Correia; Alves; Anais Fac.Farm.Porto; 14; 1954; 101,109;
Ref. 2 1053596; Journal; Macciotta; GCITA9; Gazz.Chim.Ital.; 81; 1951; 485,488;
Reactant BRN 2212160 4-(1-hydroxy-2-methylamino-ethyl)-benzen
Product BRN 84665 3-hydroxy-1-methyl-2,3-dihydro-indole-5,
-------------------------
Reagent VOCl2, O2
Solvent H2O
Temperature 25 øC
Other conditions dependence of rate constant on pH, adrenaline concentration, VOCl2 concentration; ionic strength: 0.100 mol dm%-3& (KNO3)
Subject studied Rate constant
Ref. 1 5731416; Journal; Jameson, Reginald F.; Kiss, Tamas; JCDTBI; J.Chem.Soc.Dalton Trans.; EN; 1986; 1833-1838;
-------------------------
Other conditions disproportionation during electrooxidation of title compound at carbon-fiber microelectrodes at physiological pH
Subject studied Rate constant
Mechanism
Ref. 1 5925724; Journal; Ciolkowski, Edward L.; Maness, Karolyn M.; Cahill, Paula S.; Wightman, R. Mark; Evans, Dennis H.; et al.; ANCHAM; Anal.Chem.; EN; 66; 21; 1994; 3611-3617;Reaction
Reactant BRN 2212160 4-(1-hydroxy-2-methylamino-ethyl)-benzen
Product BRN 84665 3-hydroxy-1-methyl-2,3-dihydro-indole-5,
161691 1-methyl-indole-3,5,6-triol
-------------------------
Solvent D2O
Time 350 min
Temperature 24.9 øC
Other conditions Irradiation
other sensitizers: methylene blue, rose bengal, fluoresceine, superoxide dismutase; other inhibitors: 1,3-diphenylisobenzofuran, 1,4-diazobicyclo<2,2,2>octane, KN3, NaN3; other solvent: H2O.
Subject studied Rate constant
Mechanism
Ref. 1 5689294; Journal; Kruk, I.; ZPCLAH; Z.Phys.Chem.(Leipzig); EN; 268; 3; 1987; 607-613;Reaction
Reactant BRN 2212160 4-(1-hydroxy-2-methylamino-ethyl)-benzen
Product BRN 84665 3-hydroxy-1-methyl-2,3-dihydro-indole-5,
2806381 C9H11NO3
-------------------------
Other conditions Irradiation
laser induced oxidation at pH5 at various electrodes; half life of 0-quinone
Subject studied Product distribution
Ref. 1 5562583; Journal; Skully, Joan P.; McCreery, Richard L.; ANCHAM; Anal.Chem.; EN; 52; 12; 1980; 1885-1889;
Reactant BRN 2806381 C9H11NO3
Product BRN 84665 3-hydroxy-1-methyl-2,3-dihydro-indole-5,
-------------------------
Other conditions the half life
Subject studied Rate constant
Ref. 1 5562583; Journal; Skully, Joan P.; McCreery, Richard L.; ANCHAM; Anal.Chem.; EN; 52; 12; 1980; 1885-1889;
Reactant BRN 3201122 (+-)-1-<3,4-dihydroxy-phenyl>-2-me
Product BRN 5741691 C9H9NO3
-------------------------
Reagent K3Fe(CN)6
Solvent acetic acid
H2O
Time 5 min
Temperature 5 øC
Ref. 1 5676615; Journal; Kato, Eishin; Oya, Masayuki; Uda, Kozo; Iso, Tadashi; Fujita, Tadashi; Iwao, Jun-Ichi; CPBTAL; Chem.Pharm.Bull.; EN; 29; 7; 1981; 1935-1941;
Reactant BRN 6685443 C9H11NO3
Product BRN 84667 (R)-3-hydroxy-1-methyl-indoline-5,6-dion
-------------------------
Reagent Fe(NO3)3, KNO3
Solvent H2O
Temperature 25 øC
Subject studied Rate constant
Ref. 1 5856275; Journal; Linert, Wolfgang; Herlinger, Erwin; Jameson, Reginald F.; JCPKBH; J.Chem.Soc.Perkin Trans.2; EN; 12; 1993; 2435-2439;
-the good reverend drone
Beagle
Hive Bee posted 01-25-1999 02:17 PM
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I just checked Medline, and low and behold, there has been quite a bit of work done in recent years on the physiological significance of adrenochrome.
One article that I saw on the mechanism of this transformation was Biol Signals, 5(5):275-82 1996 Sep-Oct, where it was suggested that the transformation is an enzyme mediated one, and is dependant on H2O2 and O2-. NADH also apparently stimulates the production of adrenochrome, indicating involvement of NADH dehydrogenase.
Beagle
Hive Bee posted 01-26-1999 09:53 AM
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Further searching of Medline has yielded the following papers relating to adrenochrome and mental function that may prove interesting. I don't have easy access to any of them. If anyone gets them and finds anything interesting, please post.
Molecular interactions in the phenomenology of the onset of mental illness.
Chem-Biol-Interact. 1973 Jul; 7(1): 1-9
Riv-Neurol. 1971 May-Jun; 41(3): 182-7
Clin-Chim-Acta. 1970 Oct; 30(1): 5-11
Mobius
NewBee posted 01-27-1999 09:01 AM
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In the book 'Legal Highs' (Adam Gottlieb) I found this monograph concerning Adrenochrome Semicarbazone:
Material ...)
NAMF
Hive Bee posted 02-20-2000 04:02 PM
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unless ya are a real pro I think ya would be finding a mixture of various relater type cat things from such a procedure as seems typicial however not all would be active in a single transport mechanism thats what proally makes ice so dang cool
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(Stranger)
06-29-02 22:33
No 327070
I had orderd adrenochrome from a certain chemical company and i can tell you yhat its completely worthless except for me getting a headache and a stomachache with slight slurred speech and a general bad vibe and trouble sleeping but no neusea but i did the second time at about 80mg experience a wierd head rushing sensation that was very intense and disorenting with some distortion of time i think but it did have a scopolamine/atropine type feeling of confusion that i was'nt expecting as i had plans but i ended up waking the next morning with 4 messages and a headache that could have been from the valium but overall nothing to stong at what i thought was a high dose and it lasting somewhat around 6-8 hours if it was'nt just in my head.
NOT ONE DRUG IS ACTIVE ITS ONLY THE BRAIN THAT IS