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20-September-2008 09:55:56 - Phenethylamine Phenethylamine1 Chemical structure of Phenethylamine IUPAC name 2-Phenylethylamine Other names Phenethylamine β-Phenylethylamine 2-Phenyl-1-aminoethane β-Aminoethylamine 2-Phenylethanamine Identifiers CAS number 64-04-0 SMILES c1ccccc1CCN Properties Molecular formula C8H11N Molar mass 121.18 g/mol Density 0.964 g/cm3 Melting point -60 °C Boiling point 194.5-195 °C Hazards MSDS MSDS for phenethylamine NFPA 704 2 2 2 Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Phenethylamine, or β-phenylethylamine or 2-phenylethylamine, is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer α-phenylethylamine 1-phenylethylamine, which has two stereoisomers: R-+-1-phenylethylamine and S---1-phenylethylamine. In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter trace amine. Phenethylamine is a natural compound biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. However trace amounts from food is quickly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain.23 Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine.4 D-Phenylalanine increases the brain content of phenylethylamine .5 Phenylethylamine has been shown at least indirectly to satisfy the four main criteria required to demonstrate that a neuroamine sustains mood and that its deficit can be responsible for depression.5 while at the same time inhibiting DA neuron firings.67 It also modulates noradrenergic transmission.8 Phenethylamine, along with tyramine, reversibly depresses the slow GABAB receptor inhibitory post-synaptic potential in midbrain dopaminergic cells.9 Low levels are found in those suffering from attention deficit disorder10 and often in depression, while levels are elevated in schizophrenia.11 This is associated with low dopamine in ADHD and depression and high dopamine in schizophrenia. Contents 1 Chocolate theory of love 2 Substituted phenethylamines 3 Pharmacology 4 Substitution table 5 Relation to amphetamine 6 Graphical overview 7 See also 8 References 9 External links Chocolate theory of love In the early 1980s, researcher Michael Liebowitz, author of the popular 1983 book The Chemistry of Love, remarked to reporters that chocolate is loaded with PEA. This became the focus for an article in The New York Times, which was then taken up by the wire services, then by magazine free-lancers, and evolved into the now-eponymous chocolate theory of love.12 However, as noted earlier, phenethylamine from food is rapidly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain, however when taken in higher doses it has potent perceptible psychoactive effect. Substituted phenethylamines General structure of phenethylamines and amphetamines see the table below. General structure of phenethylamines and amphetamines see the table below. Substituted phenethylamines carry additional chemical modifications at the phenyl ring, the sidechain, or the amino group: Substituted Amphetamines are homologues of phenethylamines carrying an alpha-methyl α-CH3 group at the sidechain carbon atom next to the amino group. Catecholamines are phenethylamines carrying two hydroxy groups in positions 3 and 4 of the phenyl ring. Examples are the hormones and neurotransmitters dopamine, epinephrine adrenaline, and norepinephrine noradrenaline. The aromatic amino acids phenylalanine and tyrosine are phenethylamines carrying a carboxyl group COOH in alpha position. 2Cs are phenethylamines with methoxy groups attached to the 2 and 5 carbons and no alpha-methyl group. Pharmacology The factual accuracy of this section is disputed. Please see the relevant discussion on the talk page.May 2008 August 2008 Phenylethylamine's half life is 5-10 minutes.13dubious - discuss Phenylethylamine is metabolized by MAO-A 3, MAO-B 2, aldehyde dehydrogenase and dopamine-beta-hydroxylase.13 Phenylethylamine brain levels can be increased by a 1000 fold when taking an MAO Inhibitor and 3-4 times when taken by itself.14dubious - discuss Alcohol and THC increase phenylethylamine levels by a 4 fold.14dubious - discuss Many substituted phenethylamines are pharmacologically active drugs due to their similarity to the monoamine neurotransmitters: Stimulants like the plant alkaloids ephedrine and cathinone and the synthetic drug dextroamphetamine and methylphenidate Hallucinogens like the plant alkaloid mescaline and the synthetic drug 2C-B Empathogen-entactogens like MDMA ecstasy and MDA Anorectics like phentermine, fenfluramine, and amphetamine Bronchodilators like salbutamol and ephedrine Antidepressants like venlafaxine, bupropion and the monoamine oxidase inhibitors phenelzine and tranylcypromine. Substitution table Some of the more important phenethylamines are tabulated below. For simplicity, the stereochemistry of the sidechain is not covered in the table. Hundreds of other simple synthetic phenethylamines are known. This is due in large part to the pioneering work of Alexander Shulgin, much of which is described in the book PiHKAL Phenethylamines i Have Known And Loved. Selected Phenethylamines Short Name Rα Rβ R2 R3 R4 R5 RN Full Name Tyramine OH 4-hydroxy-phenethylamine Dopamine OH OH 3,4-dihydroxy-phenethylamine Epinephrine Adrenaline OH OH OH CH3 β,3,4-trihydroxy-N-methylphenethylamine Norepinephrine Noradrenaline OH OH OH β,3,4-trihydroxyphenethylamine Phenylephrine OH OH CH3 β,3-dihydroxy-N-methylphenethylamine 6-Hydroxydopamine OH OH OH 2,4,5-trihydroxyphenethylamine Salbutamol OH OH CH2OH CCH33 β,4-dihydroxy-3-hydroxymethyl-N-tert-butyl-phenethylamine Beta-methyl-phenethylamine CH3 β-methylphenethylamine Amphetamine CH3 α-methylphenethylamine Methamphetamine CH3 CH3 N-methylamphetamine Methylphenidate N,α-butylene-β-methoxycarbonylphenethylamine Ephedrine, pseudoephedrine CH3 OH CH3 N-methyl-β-hydroxyamphetamine Acetylamphetamine CH3 COCH3 α-methyl-3-acetylphenethylamine Cathine CH3 OH β-hydroxy-amphetamine Cathinone CH3 =O β-ketoamphetamine Methcathinone CH3 =O CH3 N-methyl-β-ketoamphetamine Bupropion CH3 =O Cl CCH33 3-chloro-N-tert-butyl-β-ketoamphetamine Fenfluramine CH3 CF3 CH2CH3 3-trifluoromethyl-N-ethyl-amphetamine Phentermine 2CH3 α,α-dimethylphenethylamine Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine MDA CH3 -O-CH2-O- 3,4-methylenedioxyamphetamine MDMA CH3 -O-CH2-O- CH3 3,4-methylenedioxy-N-methylamphetamine MDMC CH3 =O -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-β-ketoamphetamine DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine 2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine 2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine 2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodophenethylamine 2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methylphenethylamine 2C-E OCH3 CH2-CH3 OCH3 2,5-dimethoxy-4-ethylphenethylamine 2C-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine 2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine 2C-T-2 OCH3 S-CH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine 2C-T-4 OCH3 S-CHCH32 OCH3 2,5-dimethoxy-4-isopropylthio-phenethylamine 2C-T-7 OCH3 S-CH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine 2C-T-8 OCH3 S-CH2-C3H5 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine 2C-T-9 OCH3 S-CCH33 OCH3 2,5-dimethoxy-4-tert-butylthio-phenethylamine 2C-T-21 OCH3 S-CH2-CH2-F OCH3 2,5-dimethoxy-4-2-fluoroethylthio-phenethylamine Short Name Rα Rβ R2 R3 R4 R5 RN Full Name Relation to amphetamine Despite the negative stigma tagged to amphetamine alpha-methylphenethylamine speed, amp, uppers and methylamphetamine N-methyl-alpha-methylphenethylamine speed, meth, ice, crystal and its recreational compunds, the phenylethylamine comprises not only these so called toxic or dangerous amphetamine or methamphetamine, it makes up many drugs with important uses including medical ones like bronchodilators; used for dilating or opening the bronchi and bronchioles, which is benefit to and can save the life of an asthmatic with salbutamol or albuterol or epinephrin for someone with life-threatening allergic reactions, important neurotransmitters like dopamine, epinephrine Adrenaline, which humans depend on for normal functioning and survival, and some medically used stimulants like amphetamine Adderall, Dexedrine, methylamphetamine Desoxyn, methylphenidate Ritalin, Concerta and others; which benefit people with ADHD and ADD attention and behavioral disorders affecting many children and some adults, narcolepsy person with insomnia that can fall asleep at anytime during the day, chronic fatigue syndromeCFS, syndrome that inflicts unexplainable pain, fatigue, interruption of normal sleep, cognitive impairments confusion, forgetfulness, and a cloudy mental or head feeling, ataxia, nausea and gastrointestinal problems like IBS and other negative symptoms, and can be used for traumatic brain injury TBS. The majority of phenylethylamines used by many have some or all of the actions of the stigmatized amphetamine and methamphetamine though sometimes they lack the recreational abuse and also share great structural similarity to methamphetamine and amphetamine. Graphical overview See also Catecholamines Alexander Shulgin PiHKAL Phenethylamines i Have Known And Loved Phenethyl alcohol 2C's References ^ Merck Index, 12th ion, 7371. ^ a b cite journal Phenylethylamine is the cause of a buzz or high produced from alcohol and cannabis. | author=Yang HY, Neff NH. | title=Beta-phenylethylamine: a specific substrate for type B monoamine oxidase of brain | journal=The Journal of Pharmacology and Experimental Therapeutics | year=1973 | pages=365-71 | volume=187 | issue=2 | pmid=4748552 ^ a b Suzuki O, Katsumata Y, Oya M. 1981. Oxidation of beta-phenylethylamine by both types of monoamine oxidase: examination of enzymes in brain and liver mitochondria of eight species. The Journal of Neurochemistry 36 3: 1298-301. doi:10.1111/j.1471-4159.1981.tb01734.x. PMID 7205271. ^ 2-Phenylethylamine as a possible mediator for THC induced stimulation 1974. Nature 248. ^ a b HECTOR C. SABELLI, RICHARD L. BORISON, BRUCE I. DIAMOND, HENRI S. HAVDALA, and NEDATHUR NARASIMHACHARI. PHENYLETHYLAMINE AND BRAIN FUNCTION. Biochemical Pharmacology 27: 1729-1730. ^ Kota Ishida, Mikio Murata et al. 2005. Effects of -Phenylethylamine on Dopaminergic Neurons of the Ventral Tegmental Area in the Rat: A Combined Electrophysiological and Microdialysis Study. Journal of Pharmacology and Experimental Therapeutics Fast Forward 314: 916. doi:10.1124/jpet.105.084764. PMID 15879004. ^ EM Parker and LX Cubeddu. Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding abstract. PMID 3129549. ^ I. A. Paterson 1993. The potentiation of cortical neuron responses to noradrenaline by 2-phenylethylamine is independent of endogenous noradrenaline. Neurochemical Resarch 18: 1329. doi:10.1007/BF00975055. ^ M Federici et al. 2005. Trace amines depress GABA B response in dopaminergic neurons by inhibiting G-betagamma-gated inwardly rectifying potassium channels abstract. Molecular Pharmacology 67: 1283-1290. doi:10.1124/mol.104.007427. PMID 15644497. ^ Baker GB et al.. Phenylethylaminergic mechanisms in attention-deficit disorder. ^ SG Potkin et al 1979. Phenylethylamine in paranoid chronic schizophrenia. Science 206: 470. doi:10.1126/science.504988. PMID 504988. ^ Liebowitz, Michael, R. 1983. The Chemistry of Love. Boston: Little, Brown, Co. ^ a b Sabelli, Hector C.; J. I. Javaid 1995. Phenylethylamine modulation of affect: therapeutic and diagnostic implications. J Neuropsychiatry Clin Neurosci 7: 6-14. PMID 7711493. ^ a b Sabelli, Hector C.; et al. 1978. Phenylethylamine and brain function. Biochem Pharmacol. 27 13: 1707-1711. doi:10.1016/0006-29527890543-9. PMID 361043. External links Book II of PiHKAL online Review and summary of PiHKAL, including table of 300+ phenethylamines: ascii postscript A Structural Tour of PiHKAL v d e Phenethylamines 2C-B 2C-C 2C-D 2C-E 2C-I 2C-N 2C-T-2 2C-T-21 2C-T-4 2C-T-7 2C-T-8 3C-E 4-FMP Bupropion Cathine Cathinone Clenbuterol DESOXY Dextroamphetamine Methamphetamine Diethylcathinone Dimethylcathinone DOC DOB DOI DOM bk-MBDB Dopamine Br-DFLY Ephedrine Epinephrine Escaline Etafedrine Fenfluramine Levosalbutamol Levmetamfetamine MBDB MDA MDMA MDMC MDEA MDPV Mescaline Methcathinone Norepinephrine Phentermine Salbutamol Tyramine Venlafaxine v d e Psychedelic phenethylamines Aleph 2C-B 2C-B-FLY 2C-C 2C-D 2C-E 2C-F 2C-G 2C-I 2C-N 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-17 2C-T-21 2C-TFM 2C-YN 25I-NBOH 25I-NBOMe 3C-E 3C-P Br-DFLY DESOXY DMMDA-2 DOB DOC DOET DOI DOM DON DOPR DOTFM Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Lophophine MDA MMDA MMDA-2 MMDA-3a MMDMA Macromerine Mescaline Proscaline TCB-2 TMA v d e Drugs from PiHKAL AEM · AL · Aleph · Aleph-2 · Aleph-4 · Aleph-6 · Aleph-7 · Ariadne · Asymbescaline · Buscaline · Beatrice · Bis-TOM · BOB · BOD · BOH · BOHD · BOM · 4-Bromo-3,5-dimethoxyamphetamine · 2-Bromo-4,5-methylenedioxyamphetamine · 2C-B · 3C-BZ · 2C-C · 2C-D · 2C-E · 3C-E · 2C-F · 2C-G · 2C-G-3 · 2C-G-4 · 2C-G-5 · 2C-G-N · 2C-H · 2C-I · 2C-N · 2C-O · 2C-O-4 · 2C-P · CPM · 2C-SE · 2C-T · 2C-T-2 · 2C-T-4 · psi-2C-T-4 · 2C-T-7 · 2C-T-8 · 2C-T-9 · 2C-T-13 · 2C-T-15 · 2C-T-17 · 2C-T-21 · 4-D · beta-D · DESOXY · 2,4-DMA · 2,5-DMA · 3,4-DMA · DMCPA · DME · DMMDA · DMMDA-2 · DMPEA · DOAM · DOB · DOBU · DOC · DOEF · DOET · DOI · DOM · psi-DOM · DON · DOPR · Escaline · EEE · EEM · EME · EMM · Ethyl-J EBDB · Ethyl-K · F-2 · F-22 · Flea · 3C-G-3 · 3C-G-4 · 3C-G-5 · 3C-G-N · Ganesha · HOT-2 · HOT-7 · HOT-17 · IDNNA · Isomescaline · Isoproscaline · Iris · J BDB · Lophophine · Mescaline · 4-MA · Madam-6 · Methallylescaline · MDA · MDAL · MDBU · MDBZ · MDCPM · MDDM · MDE · MDHOET · MDIP · MDMA · MDMC EDMA · MDMEO · MDMEOET · MDMP · MDOH · MDPEA · MDPH · MDPL · MDPR · Metaescaline · MEDA · MEE · MEM · MEPEA · Meta-DOB · Meta-DOT · Methyl-DMA · Methyl-DOB · Methyl-J MBDB · Methyl-K · Methyl-MA PMMA · Methyl-MMDA-2 · MMDA · MMDA-2 · MMDA-3a · MMDA-3b · MME · Metaproscaline · MPM · Ortho-DOT · Proscaline · Phenescaline · Phenethylamine · Propynyl · Symbescaline · 2,3,4,5-Tetramethoxyamphetamine · 3-TASB · 4-TASB · 5-TASB · Thiobuscaline · 3-TE · 4-TE · 3-TIM · 4-TIM · 5-TIM · 3-TM · 4-TM · TMA · TMA-2 · TMA-3 · TMA-4 · TMA-5 · TMA-6 · 3-TME · 4-TME · 5-TME · 2T-MMDA-3a · 4T-MMDA-2 · 2-TOET · 5-TOET · 2-TOM · 5-TOM · TOMSO · Thioproscaline · Trisescaline · 3-TSB · 4-TSB · 3-T-Trisescaline · 4-T-Trisescaline v d e Stimulants Alkylamines Cyclopentamine Geranamine Isometheptene Octodrine Propylhexedrine Tuamine Alphapyrrolidinylalkiophenones α-PPP MDPPP MDPV MPBP MPHP MPPP MOPPP Pyrovalerone Cholinergics ABT-089 ABT-418 Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine Rivanicline Tebanicline Varenicline Convulsants Bicuculline DMCM Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil Carphedon Modafinil Phenethylamines 4-Bromomethcathinone 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-Fluoromethcathinone 4-Methylmethcathinone 4-MTA Aletamine Amfepentorex Amphechloral Amphetamine Dextroamphetamine, Adderall Amphetaminil Benzphetamine Bupropion Cathinone Chlorphentermine Clenbuterol Clobenzorex Clortermine Diethylpropion Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Ephedrine Epinephrine Ethcathinone Ethylamphetamine Fenethylline Fenfluramine Fenproporex Fludorex Furfenorex Levomethamphetamine Lisdexamfetamine MDMA Mefenorex Methamphetamine Methcathinone Methoxyphedrine Methylone Octopamine Ortetamine Parahydroxyamphetamine PCA PIA PMA PMEA PMMA PPAP Phendimetrazine Phenmetrazine Phentermine Phenylephrine Phenylpropanolamine Propylamphetamine Pseudoephedrine Selegiline Synephrine Tiflorex Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex Aminorex Clominorex Fenozolone Fluminorex Pemoline Thozalinone Piperazines 2C-B-BZP BZP GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine Piperidines 2-Benzylpiperidine Desoxypipradrol Diphemethoxidine Ethylphenidate HDMP-28 --Methyl-1-methyl-4β-2-naphthylpiperidine-3β-carboxylate Methylphenidate Dexmethylphenidate Nocaine Phacetoperane Pipradrol Tropanes 3α-Bis-4-fluorophenylmethoxytropane 3α-4-Chlorophenylphenylmethoxytropane 3-Pseudotropyl-4-fluorobenzoate Altropane IACFT Brasofensine CFT WIN 35,428 β-CIT RTI-55 Cocaethylene Cocaine β-CPPIT Dichloropane RTI-111 Difluoropine FE-β-CPPIT FP-β-CPPIT PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-121 IPCIT RTI-126 RTI-150 RTI-171 RTI-177 RTI-336 Tesofensine Troparil β-CPT, WIN 35,065-2 WF-23 WF-33 WF-60 Xanthines Aminophylline Caffeine Dimethazan Paraxanthine Theobromine Theophylline Others Amineptine Bemegride Benzydamine BPAP Bromantane BTQ Clofenciclan Cypenamine Cyprodenate Diclofensine Dimethocaine Diphenyl prolinol Ethamivan Fencamfamine Feprosidnine Gilutensin GYKI-52895 Hexacyclonate Indanorex Indatraline LR-5182 Mazindol Mesocarb Naphthylisopropylamine Nikethamide Nomifensine Phthalimidopropiophenone Prolintane Sibutramine Yohimbine Zylofuramine See also Sympathomimetic amines Retrieved from http://en..org/wiki/Phenethylamine Categories: PhenethylaminesHidden categories: Accuracy disputes from May 2008 | Articles needing additional references from August 2008 | All pages needing cleanup | Articles with disputed statements from May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Català Česky Deutsch Español Français Hrvatski Italiano עברית Nederlands 日本語 Polski РуÑ?Ñ?кий SlovenÄ?ina Suomi Svenska ä¸æ–‡ This page was last modified on 21 August 2008, at 03:3
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