Adrenolutin

Last updated
Adrenolutin
Adrenolutin.svg
Names
IUPAC name
1-methylindole-3,5,6-triol
Other names
3,5,6-Trihydroxy-1-methylindole; 1-Methyl-3,5,6-trihydroxyindole
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-4,11-13H,1H3
    Key: DINWCUSJIVPQIO-UHFFFAOYSA-N
  • CN1C=C(C2=CC(=C(C=C21)O)O)O
Properties
C9H9NO3
Molar mass 179.175 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Adrenolutin, also known as 3,5,6-trihydroxy-1-methylindole, is a cyclized derivative of epinephrine (adrenaline) and claimed hallucinogen related to adrenochrome. [1] [2] [3] [4] Along with adrenochrome, adrenolutin is described as an oxidation product of epinephrine. [4] In terms of physical appearance, adrenolutin is described as colorless [4] and as intensely yellow-green fluorescent. [1] It is said to be chemically unstable, albeit considerably more stable than adrenochrome. [1] [5]

Adrenochrome and adrenolutin were studied by Abram Hoffer and Humphry Osmond in the 1950s and 1960s. [1] [5] Based on structural similarity of epinephrine and mescaline, adrenochrome was proposed by these authors as an endogenous psychotomimetic or hallucinogen, metabolite of epinephrine, and mediator in the etiology of schizophrenia. [1] [5] Adrenolutin is an analogue of adrenochrome that was claimed to have similar effects. [1] [5] The compound was said to produce psychological changes at oral doses of 25 to 50 mg in humans. [1] [2] It was said to be as active as adrenochrome but to produce fewer perceptual effects and to have a longer duration or time to recovery. [1] Adrenolutin's effects were said to include thought disorder, decreased anxiety, reduced insight into these changes, affective disharmony, and subtle physical changes. [1] The thought disorder symptoms were said to include decreased abstraction ability, problem-solving difficulty, mood changes, and resemblance to the thought disorder in schizophrenia but without the associated perceptual changes. [1] Adrenolutin was also said to potentiate the effects of LSD and vice versa. [1]

However, the purity of the adrenochrome and adrenolutin used in Hoffer and Osmond's studies was questionable, and further studies were said to be needed to confirm the possible hallucinogenic effects of the compound. [1] [2] Subsequent studies by other researchers with pure material were unable to reproduce the earlier findings, and efforts to detect adrenochrome in people with schizophrenia were unsuccessful. [5] According to Alexander Shulgin in his 1991 book PiHKAL , the notion that adrenochrome and adrenolutin are hallucinogenic is controversial and is not accepted by the scientific community. [4] Following Hoffer and Osmond's investigations of the compounds, interest in adrenochrome and adrenolutin died away and they are now considered to be little more than an interesting historical footnote. [4] John Smythies, a former collaborator of Hoffer and Osmond, continued to stand by and promote the adrenochrome hypothesis of schizophrenia as late as the early 2000s. [6] The history of the theory was critically reviewed and discussed in 2010. [7]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
  2. 1 2 3 Heacock RA, Powell WS (1972). "Adrenochrome and related compounds". Prog Med Chem. Progress in Medicinal Chemistry. 9 (2): 275–339. doi:10.1016/s0079-6468(08)70401-6. ISBN   978-0-7204-7409-1. PMID   4581204.
  3. ↑ Hoffer, A.; Osmond, H. (1967). "Adrenochrome and Some of Its Derivatives". The Hallucinogens. Elsevier. pp. 267–442. doi:10.1016/b978-1-4832-3296-6.50007-0. ISBN   978-1-4832-3296-6.
  4. 1 2 3 4 5 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. "Also there had been interest in reports that adrenalin that had become old and discolored seemed to elicit central effects in man. The oxidation products were identified as the deeply colored indolic compound adrenochrome and the colorless analogue adrenolutin. 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. But, in any case, they are not phenethylamines and so not part of this book."
  5. 1 2 3 4 5 Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN   978-0-12-290559-9. A body of literature has been built up over the last two decades concerning the possible role of some oxidation product of adrenalin as an in vivo psychotomimetic. It has been proposed, from chemical similarities between the neurotransmitter epinephrine (adrenalin) and mescaline, that some derivative of epinephrine might be generated abnormally in the body in mental illness (Osmond and Smythies, 1952). Adrenochrome (CXI) is an oxidation product easily formed from epinephrine in vivo. This material was reported to be an extremely potent compound in humans, active in leading to central changes at submilligram dosages (Hoffer et al., 1954). Another, and considerably more stable, oxidation product of epinephrine, is androlutin (CXII) which is also reported to be centrally active in humans (Hoffer, 1957). Early efforts to confirm or challenge these reports were faulted by the difficulties of obtaining and maintaining pure preparations of adrenochrome. Now that problems have been largely overcome, it is generally accepted that the initial reports cannot be duplicated. Grof et al. (1963) have noted sensory disturbances induced in normal subjects with 15-30 mg doses, but these were variable and reflected the source of the drug employed. Others have found the drug inactive (Rinkel and Solomon, 1957; Smythies, 1960), and efforts to detect it in blood samples from schizophrenic patients were futile (Szara et al., 1958). The current chemistry and pharmacological position of these indoles have been recently reviewed (Heacock, 1971).
  6. ↑ Smythies J (March 2002). "The adrenochrome hypothesis of schizophrenia revisited". Neurotox Res. 4 (2): 147–150. doi:10.1080/10298420290015827. PMID   12829415.
  7. ↑ Mills JA (May 2010). "Hallucinogens as hard science: the adrenochrome hypothesis for the biogenesis of schizophrenia". Hist Psychol. 13 (2): 178–195. doi:10.1037/a0019394. PMID   20533770.


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