Macromerine

Macromerine is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris.[1] It can also be found in C. runyonii,[2] C. elephantidens, and other related members of the family Cactaceae. The plants may have been used by Tarahumara shamans for their entheogenic effects.

Macromerine
Names
IUPAC name
(R)-1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C12H19NO3
Molar mass 225.288 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chemistry

Macromerine is in a family of chemicals called the phenethylamines and is similar in structure to epinephrine. The full chemical name of macromerine is (R)-1-(3,4-dimethoxyphenyl)-2-(dimethylamino)ethanol.

Effects

Little is known about potential psychedelic effects of macromerine. At least one study found macromerine to be non-psychoactive.[3]

References
  1. Brown, Stanley D.; Hodgkins, Joe E.; Reinecke, Manfred G. (1972). "Isolation, structure, synthesis, and absolute configuration of the cactus alkaloid, macromerine". The Journal of Organic Chemistry. 37 (5): 773–5. doi:10.1021/jo00970a024. PMID 5016327.
  2. Below, L.E.; Leung, A.Y.; Paul, A.G.; McLaughlin, J.L. (1968). "Cactus Alkaloids IV. Macromerine from Coryphantha runyonii". Journal of Pharmaceutical Sciences. 57 (3): 515–6. doi:10.1002/jps.2600570334. PMID 5655598.
  3. Vogel, W. H.; Evans, B. D.; Bonnem, E. M.; Fischer, J. F.; McLaughlin, J. L. (1973). "Macromerine, normacromerine and bisnormacromerine: Non-psychoactive methylated derivatives of norepinephrine". Psychopharmacologia. 30 (2): 145–51. doi:10.1007/BF00421429. PMID 4711372. S2CID 19823706.
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