3-O-Desmethylmescaline

Last updated

3-O-Desmethylmescaline
3-O-Desmethylmescaline.svg
Clinical data
Other names3,4-Dimethoxy-5-hydroxyphenethylamine; 3-Hydroxy-4,5-dimethoxyphenethylamine; 3-Desmethylmescaline
Identifiers
  • 5-(2-aminoethyl)-2,3-dimethoxyphenol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C10H15NO3
Molar mass 197.234 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OC)O)CCN
  • InChI=1S/C10H15NO3/c1-13-9-6-7(3-4-11)5-8(12)10(9)14-2/h5-6,12H,3-4,11H2,1-2H3
  • Key:PDKPJPTZKPCMKR-UHFFFAOYSA-N

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

Contents

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

The pharmacology of 3-O-desmethylmescaline is unknown. [1] In addition, according to Alexander Shulgin, the effects of 3-O-desmethylmescaline in humans are unknown, and it is unclear whether it might have psychedelic effects in humans similarly to mescaline. [1]

See also

References

  1. 1 2 3 4 5 6 7 8 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. pp. 45–46. ISBN   978-0-9630096-3-0 . Retrieved 2 November 2024.
  2. 1 2 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. 1 2 3 4 5 6 [[Keeper Trout & friends|Trout K]], et al. (2013). Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1) (PDF). Mydriatic Productions/Better Days Publishing. pp. 76–77.


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