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Names

4-HO-PEA
Tyramine
4-Hydroxyphenethylamine

IUPAC name

4-(2-Aminoethyl)phenol

ID 2014 · Formula C₈H₁₁NO · Molecular weight 137.179

InChI InChI=1S/C8H11NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5-6,9H2

InChI Key DZGWFCGJZKJUFP-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES NCCc1ccc(cc1)O

ChemSpider 5408
PubChem 5610
Wikidata Q165930
Wikipedia Tyramine
Trout’s Notes Tyramine. In The Cactus Alkaloids (2013, upd. 2018), pp. 26–32

Shulgin Index #126 Tyramine · Table 3Page 323Row 13

PiHKAL #14 BOD · #142 PEA

Phenethylamine: Von der Strucktur zur Funktion Tyramine: 6.1 (2) 358 · 6.3 (2) 401, 402, 403 · 8.6 (6) 882

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916), 934–937. 529 kB. https://doi.org/10.1126/science.1166127

Glennon, RA; Liebowitz, SM; Anderson, GM. Serotonin receptor affinities of psychoactive phenalkylamine analogues. J. Med. Chem., 1 Mar 1980, 23 (3), 294–299. 844 kB. https://doi.org/10.1021/jm00177a017 #13 NMR

Lewin, AH; Navarro, HA; Mascarella, SW. Structure-activity correlations for β-phenethylamines at human trace amine receptor 1. Bioorg. Med. Chem., 1 Aug 2008, 16 (15), 7415-7423. 366 kB. https://doi.org/10.1016/j.bmc.2008.06.009

Ghosal, S; Srivastava, RS. β-Phenethylamine, tetrahydroisoquinoline and indole alkaloids of Desmodium tiliaefolium. Phytochemistry, 1 Jan 1973, 12 (1), 193–197. 552 kB. https://doi.org/10.1016/S0031-9422(00)84646-4 #I MS,NMR,IR,UV,TLC

Partilla, JS; Dempsey, AG; Nagpal, AS; Blough, BE; Baumann, MH; Rothman, RB. Interaction of amphetamines and related compounds at the vesicular monoamine transporter. J. Pharmacol. Exp. Ther., 1 Oct 2006, 319 (1), 237–246. 367 kB. https://doi.org/10.1124/jpet.106.103622

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

Clark, LC; Benington, F; Morin, RD. The effects of ring-methoxyl groups on biological deamination of phenethylamines. J. Med. Chem., 1 May 1965, 8 (3), 353–355. 389 kB. https://doi.org/10.1021/jm00327a016

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

Biel, JH; Bopp, BA. Amphetamines: Structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 1–39. 1.0 MB. https://doi.org/10.1007/978-1-4757-0510-2_1

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Creation and application of psychoactive designer drugs data library using liquid chromatography with photodiode array spectrophotometry detector and gas chromatography–mass spectrometry. Talanta, 15 Feb 2009, 77 (4), 1245–1272. 1.2 MB. https://doi.org/10.1016/j.talanta.2008.07.062 #Tyramine

Broadley, KJ. The vascular effects of trace amines and amphetamines. Pharmacol. Ther., 1 Mar 2010, 125 (3), 363–375. 1.1 MB. https://doi.org/10.1016/j.pharmthera.2009.11.005 #p-tyramine

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, . 3.9 MB. #Tyramine

Maldonado, M; Pérez-Redondo, A; Quevedo, R. Synthesis and intermolecular interactions of N-benzylidenetyramines. J. Mol. Struct., 5 Jan 2017, 1127, 689–693. 830 kB. https://doi.org/10.1016/j.molstruc.2016.08.035 #1 MS,NMR,IR,other

Nakagawasai, O; Arai, Y; Satoh, S; Satoh, N; Neda, M; Hozumi, M; Oka, R; Hiraga, H; Tadano, T. Monoamine oxidase and head-twitch response in mice: Mechanisms of α-methylated substrate derivatives. Neurotoxicology, 1 Jan 2004, 25 (1), 223–232. 169 kB. https://doi.org/10.1016/S0161-813X(03)00101-3 #Tyramine

Benington, F; Morin, RD. The chemorelease of norepinephrine from mouse hearts by substituted amphetamines. J. Med. Chem., 1 Jul 1968, 11 (4), 896–897. 244 kB. https://doi.org/10.1021/jm00310a048 #3.1

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 #2 Rhodium.

Pummangura, S; McLaughlin, JL; Schifferdecker, RC. Cactus alkaloids. XLVII. β-Phenethylamines from the “Missouri Pincushion”, Coryphantha ~(Neobessya) missouriensis. J. Nat. Prod., 1 Jan 1981, 44 (5), 614–616. 261 kB. https://doi.org/10.1021/np50017a022 #Tyramine

Burchett, SA; Hicks, TP. The mysterious trace amines: Protean neuromodulators of synaptic transmission in mammalian brain. Prog. Neurobiol., 1 Aug 2006, 79 (5–6), 223–246. 477 kB. https://doi.org/10.1016/j.pneurobio.2006.07.003 #TYR

4-M-benzylamine

Phenylethanolamine · β-HO-PEA

2-HO-PEA · 2-HPEA

3-HPEA · m-Tyramine

Emoxypine

7 Dec 2019 · · Isomer Design