View source for It07:Epinephrine

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! colspan="2" align="center" bgcolor="#dddddd"|  Epinephrine <!-- replace if not identical with the article name -->
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Epinephrine2.jpg]] <!-- replace if not identical with the pagename -->
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! colspan="2" align="center" bgcolor="#dddddd"|IUPAC Systematic name
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| colspan="2" align="center"| (R)-4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
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! colspan="2" align="center" bgcolor="#dddddd"| Other name
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| colspan="2" align="center"| [http://www.google.co.uk/search?hl=en&q={{{OtherName}}}&btnG=Google+Search&meta= Adrenaline]
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! colspan="2" align="center" bgcolor="#dddddd"|Identifiers
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! align="left" bgcolor="#ddeeff" width="120"|[http://en.wikipedia.org/wiki/ATC_code ATC Code]
| align="center"| A01AD01, B02BC09, C01CA24, R01AA14, R03AA01, S01EA01 
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/CAS_number CAS number]
| align="center"|51-43-4, 150-05-0, 329-65-7, 6912-68-1
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/PubChem PubChem (CID)]
| align="center"|[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=838 838]
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specification SMILES]
| align="center"|[http://www.emolecules.com/cgi-bin/search?t=ss&q= OC1=C(O)C=CC((C@H)(CNC)O)=C1]
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! colspan="2" align="center" bgcolor="#dddddd"| Chemical Data
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| align="center"|C<sub>9</sub>H<sub>13</sub>NO<sub>3</sub> 
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Molecular_weight Molar mass]
| align="center"|183.204 g/mol
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! colspan="2" align="center" bgcolor="#dddddd"| Physical Data
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! align="left" bgcolor="#ddeeff" width="120"| Melting Point
| align="center"|212°C 
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! align="left" bgcolor="#ddeeff" width="120"| Electrical Moment
| align="center"| Dipole Moment
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! align="left" bgcolor="#ddeeff" width="120"| Optical Rotation
| align="center"| α 50.49° <ref>Abderhalden; Guggenheim; HSZPAZ; Hoppe-Seyler's Z. Physiol. Chem.; 57; 1908; 329</ref>
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! colspan="2" align="center" bgcolor="#dddddd"| Pharmacokinetic Data
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Bioavailability Bioavailability]
| align="center"|Nil
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Plasma_protein_binding Protein Binding]
| align="center"|{{{Protein_binding}}}
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Metabolism Metabolism]
| align="center"|Adrenegenic Synapse
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Elimination_half-life Half life]
| align="center"| 2 minutes
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Excretion Excretion]
| align="center"|n/a
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! colspan="2" align="center" bgcolor="#dddddd"| Therapeutic considerations
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Pregnancy_category Pregnancy cat.]
| align="center"|C (US)
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Regulation_of_therapeutic_goods Legal status]
| align="center"|Prescription Only
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! align="left" bgcolor="#ddeeff" width="120"| [http://en.wikipedia.org/wiki/Route_of_administration Routes]
| align="center"|Intravenous, Intramuscular, Endotracheal 
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==Introduction==
Epinephrine (or adrenaline) is a stress hormone; part of the catecholamine family; that induces the “fight or flight” response whereby the heart rate, breathing and pupil diameter all increase. Blood flow is also diverted from the digestive tract and skin to the legs for example, in preparation for the “fight or flight” response. It is released from the central part of the adrenal gland known as the adrenal medulla. Adrenaline targets various cells and in particular the α<sub>1</sub>, α<sub>2</sub>, β<sub>1</sub>, β<sub>2</sub> and β<sub>3</sub> adrenergic receptors.

The molecules 3D structure can be explored below.
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===β adrenergic receptors===

A member of the serpentine receptors, these receptors are located on muscle, adipose tissue and liver cells. Once binding of the hormone occurs there is a seven step process (similar mechanism for all 3 types of β receptors) that results in the formation of cAMP. This stimulates PKA phosphorylation of cellular proteins which in turn causes effects such as greater lipolysis, bronchiole dilation, heart rate and insulin release.

==Biosynthesis==

[[Image:Epinephrine_biosynth.jpg]]<ref>http://rfumsphysiology.pbwiki.com/f/nt%202.bmp</ref>

Epinephrine is a product in the synthesis of catecholamines from the amino acid tyrosine. The key step in this reaction sequence is that of Dopa to Dopamine. This is because low levels of dopamine as this causes schizophrenia, whilst at high levels

==Commercial Synthesis==

Due to the effects of epinephrine, it is used in the treatment of cardiac arrests as it induces ventricular relaxation via β<sub>1</sub> and β<sub>2</sub> adrenergic receptors<ref>A. Kaumann, S. Bartel, P. Molenaar, L. Sanders, K. Burrell, D. Vetter, P. Hempel, P. Karczewski and E. G. Krause, Circulation, 1999, 99, 65-72.</ref>. Hence synthetic routes such as the following are of importance beyond biosynthesis. This reaction is an example of synthesis of epinephrine from readily available reagents<ref>R. A. R. Singer, Tetrahedron Letters, 1997, 38, 927.</ref>. The enantiomer specific reaction yield of 47% is obtained in reasonable time and reaction conditions.

[[Image:Epinephrine_commercial2.jpg]]

==Synthetic Analogs of Epinephrine==

Agonists such as isoproterenol (synthetic route below<ref>G. G. Fodor, Journal of the American Chemical Society, 1949, 71, 1045.</ref>) imitate the effect of epinephrine with similar (or even slightly better) affinity.

[[Image:Isoproterenol.jpg]]

Antagonists such as propranolol (synthetic route below<ref>A. A. Solladie-Cavallo, Tetrahedron Letters, 1990, 31, 2157.</ref>) merely block the effect from occurring by obstructing the receptor site with far superior affinity than epinphrine.

[[Image:Propranolol.jpg]]

These synthetic analogs provide ways in which to counter the negative effects that epinephrine can induce such as platelet aggregation<ref>R. E. Raulli, B. Jackson, N. Tandon, M. Mattson, K. Rice and G. A. Jamieson, Biochimica Et Biophysica Acta-Molecular Cell Research, 1994, 1224, 175-180.</ref>.

==IR Condensed Phase Spectrum<ref>http://webbook.nist.gov/cgi/cbook.cgi?ID=C51434&Units=SI&Mask=80#IR-Spec</ref>==

[[Image:Epinephrine_IR.jpg]]

==(-)-Adrenaline hydrogen (+)-tartrate Crystal Structure==

C<sub>9</sub>H<sub>14</sub>NO<sub>3</sub><sup>+</sup>,   C<sub>4</sub>H<sub>5</sub>O<sub>6</sub><sup>-</sup>


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== Commercial Availability ==
Adrenaline is not easily commercially available, although through prescription it is available for a patient to self treat anaphylactic shock; essentially an allergic reaction to for example, peanuts. Commercially marketed as the "Epi-Pen", the dosage is contained in a spring loaded needle that is jabbed firmly into the thigh for use. 

==References==

<references/>