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Exploring Synephrine. To explore a different substance…

Names

Synephrine
β,4-Dihydroxy-N-methylphenethylamine
β-HO-N-Me-HPEA

IUPAC name

4-[1-Hydroxy-2-(methylamino)ethyl]phenol

ID 5547 · Formula C₉H₁₃NO₂ · Molecular weight 167.205

InChI InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3

InChI Key YRCWQPVGYLYSOX-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CNCC(c1ccc(cc1)O)O

ChemSpider 6904
PubChem 7172
Wikidata Q421351
Wikipedia Synephrine
Trout’s Notes Synephrine. In The Cactus Alkaloids (2013, upd. 2018), pp. 38–39

Shulgin Index See #71 Hordenine · Table 3Page 323Row 19

Phenethylamine: Von der Strucktur zur Funktion Synephrine: 6.3 (4) 402

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. https://doi.org/10.1111/j.1476-5381.1973.tb08331.x

Cohen, PA; Avula, B; Venhuis, B; Travis, JC; Wang, Y; Khan, IA. Pharmaceutical doses of the banned stimulant oxilofrine found in dietary supplements sold in the USA. Drug Test. Anal., 1 Jan 2017, 9 (1), 135–142. 815 kB. https://doi.org/10.1002/dta.1976

Pawar, RS; Grundel, E. Overview of regulation of dietary supplements in the USA and issues of adulteration with phenethylamines (PEAs). Drug Test. Anal., 1 Mar 2017, 9 (3), 500-517. 601 kB. https://doi.org/10.1002/dta.1980

N-Me-DHPEA · Deoxyepinephrine

3-MT · 3-Methoxytyramine · GEA

5548

DHA · HHA · α-Me-DA · α-Methyldopamine

homo-Dopamine

Phenylephrine · β-HO-N-Me-3-HPEA

p-Hydroxynorephedrine · β-HO-PHA

β-HO-4-MPEA · β-Hydroxy-4-methoxyphenethylamine

2,3-HMPEA

2,4-MHPEA

β-Me-DHPEA

4-O-Methyldopamine · HMPEA

β,2-HO-5-MePEA

2,5-HMPEA

3,5-HMPEA

2,6-HMPEA

5-DM-2C-H · 5-HO-2-MPEA

2,5-HO-4-MePEA

Metaraminol · β-HO-3-HA

10031

Ecgonidine

Norecgonidine methyl ester

3-Methoxy-β-hydroxyphenethylamine

7 Dec 2019 · · Isomer Design