Macromerine

Macromerine
Names
IUPAC name
(R)-1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol
Other names
β-Hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine; β-Hydroxy-N,N-dimethyl-DMPEA; N,N-Dimethyl-DME; N,N-Me-DME
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3 checkY
    Key: YAIPYAQVBZPSSC-UHFFFAOYSA-N checkY
  • InChI=1/C12H19NO3/c1-13(2)8-10(14)9-5-6-11(15-3)12(7-9)16-4/h5-7,10,14H,8H2,1-4H3
  • O(c1ccc(cc1OC)C(O)CN(C)C)C
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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Macromerine, also known as β-hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine, is a phenethylamine derivative.

It was first identified from cacti of the genus Pelecyphora.

At least one study found macromerine to be non-psychoactive.

See also

References

  1. ↑ Keeper Trout & friends (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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.