Macromerine

Macromerine
Names
	IUPAC name (R)-1-(3,4-Dimethoxyphenyl)-2-(dimethylamino)ethanol
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 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.^{[speculation?]}

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

^ 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.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine