4-O-Desmethylmescaline

4-O-Desmethylmescaline
Clinical data
Other names4-O-Desmethylmescaline; 4-Desmethylmescaline; 3,5-Dimethoxy-4-hydroxyphenethylamine; 4-Hydroxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxytyramine; DESMETHYL; NSC-167759; NSC-167759
Identifiers
  • 4-(2-aminoethyl)-2,6-dimethoxyphenol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15NO3
Molar mass197.234 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1O)OC)CCN
  • InChI=1S/C10H15NO3/c1-13-8-5-7(3-4-11)6-9(14-2)10(8)12/h5-6,12H,3-4,11H2,1-2H3
  • Key:ISVPPMXWQFCRSS-UHFFFAOYSA-N

4-O-Desmethylmescaline, also known as 3,5-dimethoxy-4-hydroxyphenethylamine, 3,5-dimethoxytyramine, or DESMETHYL, is an alkaloid and drug of the phenethylamine and scaline families related to mescaline.[1][2] It is the analogue of mescaline in which the methyl ether at the 4-position hydroxyl group has been removed.[1][2]

The compound occurs naturally in various cacti species, for instance those of the genera Lophophora, Trichocereus, Opuntia, and Stenocereus, among others.[1] It also occurs in certain Acacia species.[1] 4-O-Desmethylmescaline may be a biosynthetic precursor of mescaline in cacti and is also known to be a minor metabolite of mescaline.[1][3][4]

It is known to be pharmacologically active in cats, including producing catatonia and a hypokinetic rigid syndrome similarly to large doses of mescaline.[1][5] According to Alexander Shulgin, the effects of 4-O-desmethylmescaline in humans are unknown, and it is unclear whether it might have psychedelic effects similarly to mescaline.[1] However, according to John Raymond Smythies, 4-O-desmethylmescaline has no hallucinogenic activity, although this conclusion was based on the Winter and Flataker rope-climbing test in rats (where mescaline is active, 3,4-dimethoxyphenethylamine is 50% as active as mescaline, and 4-O-desmethylmescaline is completely inactive), rather than on tests in humans.[6][5][7][8]

See also

References

  1. ^ a b c d e f g Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. pp. 42–45. ISBN 978-0-9630096-3-0. Retrieved 2 November 2024.
  2. ^ a b Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. p. 742. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025.
  3. ^ Cassels BK, Sáez-Briones P (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline" (PDF). ACS Chemical Neuroscience. 9 (10): 2448–2458. doi:10.1021/acschemneuro.8b00215. PMID 29847089.
  4. ^ Dinis-Oliveira RJ, Pereira CL, da Silva DD (2019). "Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions". Current Molecular Pharmacology. 12 (3): 184–194. doi:10.2174/1874467211666181010154139. PMC 6864602. PMID 30318013.
  5. ^ a b Patel AR (1968). "Mescaline and related compounds". Fortschr Arzneimittelforsch. 11: 11–47. doi:10.1007/978-3-0348-7062-7_1. PMID 4873202. SMYTHIES and LEVY [358] compared the psychopharmacological behavior of some mescaline analogs using the rope climbing test. They found that the removal of the 5-OCH3 group from mescaline caused a 50 % decrease in activity, while demethylation of the 4-OCH3 group resulted in complete loss of activity. Substitution of benzyloxy group for the 4-OCH3 group increased the activity. Dopamine had very little behavioral effect but 5-hydroxydopamine had a moderate degree of activity.
  6. ^ Downing DF (1962). "The chemistry of the psychotomimetic substances". Quarterly Reviews, Chemical Society. 16 (2). Royal Society of Chemistry (RSC): 133. doi:10.1039/qr9621600133. ISSN 0009-2681. The available analogues of mescaline which have been tested have, in general, less psychotomimetic activity than mescaline itself. Smythies26 has started an investigation of mescaline analogues and has mentioned that 3,4-dimethoxyphenethylamine has half the activity of mescaline, whereas 4-hydroxy-3,5-dimethoxyphenethylamine has none and 4-benzyloxy-3,5-dimethoxyphenethylamine has greater activity than mescaline. [...] 26 Smythies, Lancet, 1960, I, 1287
  7. ^ Smythies JR (June 1960). "Recent advances in the biochemistry of psychosis". Lancet. 1 (7137). London, England: 1287–1289. doi:10.1016/s0140-6736(60)92265-0. PMID 13832251. A start has been made at the Worcester Foundation (Smythies and Levy 1960) where the effect of all available analogues of mescaline have been investigated, using the Winter and Flataker (1958) rat rope-climbing test. 3 : 4 dimethoxyphenylethylamine has only half the activity of mescaline (3 : 4 : 5 trimethoxyphenylethylamine). Replacement of the methoxy group in the 4 position by a hydroxy group abolishes all activity where its replacement by a benzyloxy group increases activity.
  8. ^ Smythies JR, Levy CK (April 1960). "The comparative psychopharmacology of some mescaline analogues". The Journal of Mental Science. 106 (443): 531–536. doi:10.1192/bjp.106.443.531. PMID 13832250.
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