Macromerine

Macromerine
Names
	IUPAC name (R)-1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol
	Other names β-Hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine
Identifiers
CAS Number	2970-95-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	144706 ;
PubChem CID	165055;
UNII	I2097PW32Q ;
CompTox Dashboard (EPA)	DTXSID70894756 ;
	InChI 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 Key: YAIPYAQVBZPSSC-UHFFFAOYSA-N ; 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;
	SMILES O(c1ccc(cc1OC)C(O)CN(C)C)C;
Properties
Chemical formula	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). verify (what is ?) Infobox references

Macromerine, also known as β-hydroxy-3,4-dimethoxy-N,N-dimethylphenethylamine, 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.

Chemistry

Macromerine is a phenethylamine derivative with the molecular formula C₁₂H₁₉NO₃.

Effects

At least one study found macromerine to be non-psychoactive.^[3]

References

^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

Chemistry

Effects

See also

References