ChemWiki - User contributions [en]

It07:Gentamycin

2007-11-15T10:52:12Z

Hjs106: /* Gentamycin A */ uploaded SMILES string, removed picture at top of article, uploaded picture of molecule

== Gentamycin A==
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Gentamycin is an aminoglycoside antibiotic, which can be used to treat several bacterial infections, especially those of the gram-negative variety.

It cannot be taken orally in order for it to work effectively, and so must be taken intravenously, intramuscularly or topically.
Its benefits are used to help treat bacterial infections such as Pseudomonas, Proteus, Serratia, and gram-positive Staphylococcus.

Unwanted side effects of taking Gentamycin include possible kidney function problems, as it is nephrotoxic, and also hearing problems due to general aminoglycosides being toxic to the sensory cells of the ear.

{{Drug-Box |
| Box_Name = Gentamycin A
| ImageFile = gentamicin.png
| IUPACName = 2-[4,6-diamino-3- [3-amino-6-(1-methylaminoethyl) tetrahydropyran-2-yl] oxy-2-hydroxy- cyclohexoxy]-5-methyl- 4-methylamino-tetrahydropyran-3,5-diol
| OtherName = Gentamicin
| CASNo = 1403-66-3
| ATC_Code = D06AX07 J01GB03, S01AA11, S02AA14, S03AA16
| PubChem = 3467
| SMILES = CC(C(C(O)C(OC2C(C(OC3OC(C(NC)C)CCC3N)C(N)CC2N)O)OC1)N([H])C)1O
| Formula = C21H43N5O7
| MolarMass = 477.596 g/mol
| Bioavailability = Limited oral bioavailability
| Protein_binding = 0-10%
| Metabolism =
| Half_life = 2 hours
| Excretion = Renal
| Pregnancy_cat =
| Legal_status =
| Routes = IV/IM
}}

File:Gentamicin.png

2007-11-15T10:44:54Z

Hjs106:

It07:Gentamycin

2007-11-15T10:32:51Z

Hjs106: /* Gentamycin A */ uploaded 3D molecule

== Gentamycin A==

[[Image:800px-Gentamicin.png]]

{{Drug-Box |
| Box_Name = Gentamycin A
| ImageFile =
| IUPACName = 2-[4,6-diamino-3- [3-amino-6-(1-methylaminoethyl) tetrahydropyran-2-yl] oxy-2-hydroxy- cyclohexoxy]-5-methyl- 4-methylamino-tetrahydropyran-3,5-diol
| OtherName = Gentamicin
| CAS_No = 1403663
| ATC_Code = D06AX07 J01GB03, S01AA11, S02AA14, S03AA16
| PubChem = 3467
| Formula = C21H43N5O7
| MolarMass = 477.596 g/mol
| Bioavailability = Limited oral bioavailability
| Protein_binding = 0-10%
| Metabolism =
| Half_life = 2 hours
| Excretion = Renal
| Pregnancy_cat =
| Legal_status =
| Routes = IV/IM
}}

Gentamycin is an aminoglycoside antibiotic, which can be used to treat several bacterial infections, especially those of the gram-negative variety.

It cannot be taken orally in order for it to work effectively, and so must be taken intravenously, intramuscularly or topically.
Its benefits are used to help treat bacterial infections such as Pseudomonas, Proteus, Serratia, and gram-positive Staphylococcus.

Unwanted side effects of taking Gentamycin include possible kidney function problems, as it is nephrotoxic, and also hearing problems due to general aminoglycosides being toxic to the sensory cells of the ear.

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It07:Gossypol

2007-11-01T22:16:26Z

Hjs106: /* Gossypol */ Rearranged the formatting on page. Added Introduction title, Linked references

=Introduction=
{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem = 24895349
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C30H30O8
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Cation = May be irritating to gastrointestinal tract. Large does have caused edema of lungs, | shortness of breath and paralysis in animals. Toxic to nonruminant animals, such as humans, | | by reducing the capacity the blood has to carry oxygen.
| Legal_status =
| Routes =
}}

{| border="1" cellspacing="0" colspan="2" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy UV-Vis]
|-
| [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy λmax]
| ? [http://en.wikipedia.org/wiki/Nanometre nm]
|-
| [http://en.wikipedia.org/wiki/Extinction_coefficient Extinction coefficient], ε
| ?
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Infrared_spectroscopy IR]
|-
| Major absorption bands
| ? [http://en.wikipedia.org/wiki/Centimetre cm]−1
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/NMR_Spectroscopy NMR]
|-
| [http://en.wikipedia.org/wiki/Proton_NMR Proton NMR] 
|  
|-
| [http://en.wikipedia.org/wiki/Carbon-13_NMR Carbon-13 NMR] 
| [https://www.ch.imperial.ac.uk/wiki/images/b/bd/Gossypol_C13NMR.jpg Carbon-13NMR]
|-
| Other NMR data 
|  
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Mass_Spectrometry MS]
|-
| Masses of main fragments
|   
|-
|}

Gossypol, C30H30O8, is a pigment named after the species of cotton ''gossypium L., malvaceae'', that bears the seeds from which it is extracted. Initially known only as an undesirable toxin found in foods that contained cottonseed oil, it was thought to have potential uses as a rubber antioxidant, a stabilizer for vinyl polymers and as a potential insecticide. Today it is known primarily as a male oral contraceptive, after the discovery of remarkable fertility suppressive effects in men.

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<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
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= History =

In 1929, to investigate anecdotal evidence that families who cooked with crude cottonseed oil produced fewer children, a large scale Chinese fertility survey was carried out. The study concluded that it was this oil that affected male fertility, and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception. '[I'd like to see sources for the previous paragraph please]'

In late 2005, a team of researchers at Sunderland University found that gossypol has been seen to help stop the spread of psoriasis, a fairly common and unpleasant genetic skin condition, as well as reducing inflammation in sufferers. Psoriasis suffers have a genetic fault that means that under certain conditions their skin starts to produce far too many skin cells.

=Uses and side effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organisation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.<ref>http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=9639146&dopt=Citation</ref>

Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis<ref>http://www.clevelandclinic.org/health/health-info/docs/2400/2452.asp?index=9499</ref> is also known as 'familial paralysis', and occurs due to low levels of potassium in the body. During an attack of paralysis, muscle weakness occurs in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal.

Recovery of those who used gossypol is 75%; however, it can lead to other related symptoms such as smaller testicular colume, and elevated follicle stimulating hormone concentrations.

= Known hazards =

May be irritating to gastrointestinal tract. Large doses have caused edema of lungs, shortness of breath and paralysis in animals. Toxic to nonruminant animals such as humans, by reducing the capacity the blood has to carry oxygen.

A large-scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects.

A man who uses the drug for protracted periods could become partially, if not fully, infertile.

= References =
<references/>

*http://www.emolecules.com/cgi-bin/more?vid=538892#

*The Merck Index- An Encylopedia of Chemicals, Drugs and Biologicals, Thirteenth edition, Merck & Co., Inc.

*http://news.bbc.co.uk/1/hi/england/wear/4284602.stm

*http://www.malecontraceptives.org/methods/gossypol.php

It07:Bufotoxin

2007-11-01T22:05:23Z

Hjs106: /* Bufotoxin */ Changed the chembox for Bufotoxin and Serotonin, Rearranged the images' positions

=Bufotoxin=
<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image: bufotenin.gif|Bufotenin 2D image]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-(2-Dimethylamino-ethyl)-1''H''-indol-5-ol
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C12H16N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| OC1=CC2=C(NC=C2CCN(C)C)C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 204.27 gmol-1
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 419.65 K <ref>I. J. Pachter, D. E. Zacharias and O. Ribeiro, J. Org. Chem., 1959, 24, 1285-1287.{{DOI|10.1021/jo01091a032}}</ref>
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

Bufotoxin is a composition of toxins that are used by some toads (genus Bufo). It can be found on the skin of the toads as well as in the venom and the parotoid glands. The toxin consists of a mixture of:

5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Epinephrine epinephrine], norepinephrine, and serotonin.

The composition of the toxin depends where exactly the toxin comes from. Some plants mushrooms and amphibians also use the toxin.
=Bufotenin (''also'' Bufotenine)=

Bufotenin (a typtamine alkaloid)is used by some animals for there hallucinogenic ability in a defence system. It is found in mushrooms, some plants, mammals and possibly in bodily fluids of schizophrenics.

==3D representation of ''Bufotenin molecule''==

<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1</script>
<inlineContents>Bufotoxin
DSViewer 3D 0

15 16 0 0 0 0 0 0 0 0999 V2000
1.4600 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 1
2.4600 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 2
0.4700 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 3
3.4600 -1.5600 0.0000 N 0 0 0 0 0 0 0 0 0 4
-1.5200 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 5
0.4700 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 6
4.4600 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 7
3.4600 -3.1700 0.0000 C 0 0 0 0 0 0 0 0 0 8
-1.5200 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 9
-2.5100 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 10
-0.5200 1.6600 0.0000 N 0 0 0 0 0 0 0 0 0 11
-2.5100 1.6600 0.0000 C 0 0 0 0 0 0 0 0 0 12
-3.5100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 13
-3.5100 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 14
-4.5100 -1.5600 0.0000 O 0 0 0 0 0 0 0 0 0 15
1 2 1 0 0 0
1 3 1 0 0 0
2 4 1 0 0 0
3 5 1 0 0 0
3 6 2 0 0 0
4 7 1 0 0 0
4 8 1 0 0 0
5 9 2 0 0 0
5 10 1 0 0 0
6 11 1 0 0 0
9 11 1 0 0 0
9 12 1 0 0 0
10 13 2 0 0 0
12 14 2 0 0 0
13 14 1 0 0 0
13 15 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

==3D model of Bufotenin unit cell==

<jmol>
<jmolApplet>
<title>Pentahelicene</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>BUFTEN.cif</uploadedFileContents>
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<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
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==Spectral data==
''Infrared spectrum''

IR peaks (Nujol): 3620 cm-1 [http://pubs.acs.org/cgi-bin/article.cgi/joceah/2002/67/i07/html/jo0110597.html journal] <ref>G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.{{DOI|10.1021/jo0110597}}</ref>

''NMR''

''1H NMR'' peaks (D2O): adapted from [http://pubs.acs.org/cgi-bin/article.cgi/joceah/2002/67/i07/html/jo0110597.html journal]<ref>G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.{{DOI|10.1021/jo0110597}}</ref>

{| class="wikitable"
{| border="3"

|-

! Chemical shift

! Splitting multiplicity

! Integration

! Coupling constant (J/Hz)

|-

| 2.76

| singlet

| 6H

| N\A

|-

| 2.95

| triplet

| 2H

| 7.5

|-

| 3.18

| triplet

| 2H

| 7.5

|-

| 6.86

| double doublet

| 1H

| 8.8, 2.6

|-

| 7.02

| doublet

| 1H

| 2.6

|-

| 7.15

| singlet

| 1H

| N\A

|-

| 7.38

| doublet

| 1H

| 8.8

|}

''Mass Spectrum ''

[[Image:Bufomass.JPG|Mass spectrum of Bufotenin<ref>T. O. G. Costa, R. A. V. Morales, J. P. Brito, M. Gordo, A. C. Pinto and J. C. Bloch, Toxicon, 2005, 46, 371-375.
{{DOI|10.1016/j.toxicon.2005.02.006}}</ref>]]

=Human experience of Bufotenin vapour=

After inhaling the fumes from the bufotenin the inital effect is an increased intensity of visuals and and anxiety accompanied by a general increased awareness. The next step in the experience is hallucinating and seeing swirling around the room with sweating. After a while the sweating and anxiety stops and a more relexed atmosphere still with strong hallucinating effects occurs. After a couple of hours the effect wears off into nothing. The effect of the bufotenin can depend on which form the bufotenin is in e.g. calcium bufotenin or bufotenin hydrochloride can have very different effects.<ref>Erowid experience vaults:http://www.erowid.org/experiences/exp.php?ID=64707</ref>

=Serotonin=
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | Serotonin 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Serotonin.jpg|Serotonin Structure]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-(2-aminoethyl)-1H-indol-5-ol
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C10H12N2O
|-
| [http://en.wikipedia.org/wiki/PubChem]
| 5202
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number]
| 50-67-9
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| OC1=CC=C(NC=C2CCN)C2=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 176.215 gmol-1
|-
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

3D Representation of ''Serotonin''

<jmol>
<jmolApplet>
<title>Serotonin</title><color>Black</color>
<size>200</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Serotonin3d.pdb</uploadedFileContents>
</jmolApplet>

<jmolMenu>
<item><text>Start spinning</text><script>spin on</script></item>
<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
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Serotonin picrate monohydrate ''Crystal Unit Cell'' (C10H13N2O+, C6H2N3O7-, H2O)

<jmol>
<jmolApplet>
<title>Serotonin</title><color>Black</color>
<size>200</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Serotoninunit.cif</uploadedFileContents>
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<jmolMenu>
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<item><text>Stop spinning</text><script>spin off</script></item>
<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

=References=

<references/>

It07:Bufotoxin

2007-11-01T21:29:19Z

Hjs106: /* Bufotoxin */

=Bufotoxin=
<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 3-(2-Dimethylamino-ethyl)-1''H''-indol-5-ol

|-
| Other names
| Lignocaine, L-Caine, Lidocaine(VAN), Maricaine, Ruicana, Solcain, Xylocaine, Xylocard, Xylestesin, Xylocitin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C12H16N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| OC1=CC2=C(NC=C2CCN(C)C)C=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 204.27 gmol-1
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 137-58-6
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 419.65 K <ref>I. J. Pachter, D. E. Zacharias and O. Ribeiro, J. Org. Chem., 1959, 24, 1285-1287.{{DOI|10.1021/jo01091a032}}</ref>
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}

Bufotoxin is a composition of toxins that are used by some toads (genus Bufo). It can be found on the skin of the toads as well as in the venom and the parotoid glands. The toxin consists of a mixture of:

5-MeO-DMT, bufagins, bufotalin, bufotenine, bufothionine, [http://www.ch.imperial.ac.uk/wiki/index.php/It07:Epinephrine epinephrine], norepinephrine, and serotonin.

The composition of the toxin depends where exactly the toxin comes from. Some plants mushrooms and amphibians also use the toxin.

==Bufotenin (''also'' Bufotenine)==

Bufotenin (a typtamine alkaloid)is used by some animals for there hallucinogenic ability in a defence system. It is found in mushrooms, some plants, mammals and possibly in bodily fluids of schizophrenics.

[[Image: bufotenin.gif|thumb|right|200|Bufotenin 2D image]]

===3D representation of ''Bufotenin molecule''===

<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1</script>
<inlineContents>Bufotoxin
DSViewer 3D 0

15 16 0 0 0 0 0 0 0 0999 V2000
1.4600 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 1
2.4600 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 2
0.4700 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 3
3.4600 -1.5600 0.0000 N 0 0 0 0 0 0 0 0 0 4
-1.5200 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 5
0.4700 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 6
4.4600 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 7
3.4600 -3.1700 0.0000 C 0 0 0 0 0 0 0 0 0 8
-1.5200 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 9
-2.5100 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 10
-0.5200 1.6600 0.0000 N 0 0 0 0 0 0 0 0 0 11
-2.5100 1.6600 0.0000 C 0 0 0 0 0 0 0 0 0 12
-3.5100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 13
-3.5100 0.8500 0.0000 C 0 0 0 0 0 0 0 0 0 14
-4.5100 -1.5600 0.0000 O 0 0 0 0 0 0 0 0 0 15
1 2 1 0 0 0
1 3 1 0 0 0
2 4 1 0 0 0
3 5 1 0 0 0
3 6 2 0 0 0
4 7 1 0 0 0
4 8 1 0 0 0
5 9 2 0 0 0
5 10 1 0 0 0
6 11 1 0 0 0
9 11 1 0 0 0
9 12 1 0 0 0
10 13 2 0 0 0
12 14 2 0 0 0
13 14 1 0 0 0
13 15 1 0 0 0
M END</inlineContents>
</jmolApplet>
</jmol>

===3D model of Bufotenin unit cell===

<jmol>
<jmolApplet>
<title>Pentahelicene</title><color>black</color>
<size>300</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>BUFTEN.cif</uploadedFileContents>
</jmolApplet>

<jmolMenu>
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<menuHeight>-1</menuHeight>
</jmolMenu>
<jmolButton>
<script>console</script>
<text>open a console window</text>
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''Infrared spectrum''

IR peaks (Nujol): 3620 cm-1 [http://pubs.acs.org/cgi-bin/article.cgi/joceah/2002/67/i07/html/jo0110597.html journal] <ref>G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.{{DOI|10.1021/jo0110597}}</ref>

''NMR''

''1H NMR'' peaks (D2O): adapted from [http://pubs.acs.org/cgi-bin/article.cgi/joceah/2002/67/i07/html/jo0110597.html journal]<ref>G. Revial, I. Jabin, S. Lim and M. Pfau, J. Org. Chem., 2002, 67, 2252-2256.{{DOI|10.1021/jo0110597}}</ref>

{| class="wikitable"
{| border="3"

|-

! Chemical shift

! Splitting multiplicity

! Integration

! Coupling constant (J/Hz)

|-

| 2.76

| singlet

| 6H

| N\A

|-

| 2.95

| triplet

| 2H

| 7.5

|-

| 3.18

| triplet

| 2H

| 7.5

|-

| 6.86

| double doublet

| 1H

| 8.8, 2.6

|-

| 7.02

| doublet

| 1H

| 2.6

|-

| 7.15

| singlet

| 1H

| N\A

|-

| 7.38

| doublet

| 1H

| 8.8

|}

''Mass Spectrum''

[[Image:Bufomass.JPG|thumb|left|Mass spectrum of Bufotenin<ref>T. O. G. Costa, R. A. V. Morales, J. P. Brito, M. Gordo, A. C. Pinto and J. C. Bloch, Toxicon, 2005, 46, 371-375.
{{DOI|10.1016/j.toxicon.2005.02.006}}</ref>]]

==Human experience of Bufotenin vapour ==

<ref>Erowid experience vaults:http://www.erowid.org/experiences/exp.php?ID=64707</ref>

After inhaling the fumes from the bufotenin the inital effect is an increased intensity of visuals and and anxiety accompanied by a general increased awareness. The next step in the experience is hallucinating and seeing swirling around the room with sweating. After a while the sweating and anxiety stops and a more relexed atmosphere still with strong hallucinating effects occurs. After a couple of hours the effect wears off into nothing. The effect of the bufotenin can depend on which form the bufotenin is in e.g. calcium bufotenin or bufotenin hydrochloride can have very different effects.

==Serotonin==

''General Information''

IUPAC Name: 3-(2-aminoethyl)-1H-indol-5-ol

Molecular Formula: C10H12N2O

Molecular weight: 176.215 g/mol

Smile: OC1=CC=C(NC=C2CCN)C2=C1

PubChem: 5202

[[Image:Serotonin.jpg|thumb|right|200|Serotonin Structure]]

3D Representation of ''Serotonin''

<jmol>
<jmolApplet>
<title>Serotonin</title><color>Black</color>
<size>200</size>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<uploadedFileContents>Serotonin3d.pdb</uploadedFileContents>
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<menuHeight>-1</menuHeight>
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<script>console</script>
<text>open a console window</text>
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Serotonin picrate monohydrate ''Crystal Unit Cell'' (C10H13N2O+, C6H2N3O7-, H2O)

<jmol>
<jmolApplet>
<title>Serotonin</title><color>Black</color>
<size>200</size>
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<jmolButton>
<script>console</script>
<text>open a console window</text>
</jmolButton>
</jmol>

=References=

<references/>

It07:Lignocaine

2007-11-01T21:15:15Z

Hjs106: /* Potency of Lidocaine */

It07:Lignocaine

2007-11-01T21:14:44Z

Hjs106: /* References */ edited citations for potency

Standard state

2007-11-01T20:37:56Z

Hjs106: New page: http://en.wikipedia.org/wiki/Standard_state

http://en.wikipedia.org/wiki/Standard_state

It07:Lignocaine

2007-11-01T20:36:25Z

Hjs106: /* Lignocaine */ Removed Sections hazards, supplementary data page, related compounds and structure

It07:Lignocaine

2007-11-01T20:30:42Z

Hjs106: /* Lignocaine */ Removed Structure section

It07:Lignocaine

2007-11-01T20:29:45Z

Hjs106: /* Lignocaine */ Removed all under properties except MP

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, L-Caine, Lidocaine(VAN), Maricaine, Ruicana, Solcain, Xylocaine, Xylocard, Xylestesin, Xylocitin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CC1=C(NC(CN(CC)CC)=O)C(C)=CC=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 137-58-6
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug known as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

=Potency of Lidocaine=
Substituting the amide nitrogen of lidocaine with an aminoethyl group increased the potency and improved the therapeutic index over the corresponding secondary amides when tested in mice.

=References=
#{{ Citation| last=McMaster
| first=Paul D.
| last2=Byrnes
| first2=Eugene W.
| last3=Block
| first3=Alan J.
| last4=Tenthorey
| first4=Paul A.
| title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents
| journal=J. Med. Chem.
| volume=24
| issue=1
| year=1981
| pages=53-58
| url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

It07:Lignocaine

2007-11-01T20:24:17Z

Hjs106: Added other names, SMILES, CAS. Removed appearance due to nature of pharmaceutical product.

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, L-Caine, Lidocaine(VAN), Maricaine, Ruicana, Solcain, Xylocaine, Xylocard, Xylestesin, Xylocitin
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| CC1=C(NC(CN(CC)CC)=O)C(C)=CC=C1
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 137-58-6
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug known as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

=Potency of Lidocaine=
Substituting the amide nitrogen of lidocaine with an aminoethyl group increased the potency and improved the therapeutic index over the corresponding secondary amides when tested in mice.

=References=
#{{ Citation| last=McMaster
| first=Paul D.
| last2=Byrnes
| first2=Eugene W.
| last3=Block
| first3=Alan J.
| last4=Tenthorey
| first4=Paul A.
| title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents
| journal=J. Med. Chem.
| volume=24
| issue=1
| year=1981
| pages=53-58
| url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

It07:Lignocaine

2007-11-01T20:11:06Z

Hjs106: resized Jmol image

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, Xylocaine, Xylocard
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| {{{SMILES}}}
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| {{{CASNo}}}
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug known as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
<jmolApplet>
<size>300</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

=Potency of Lidocaine=
Substituting the amide nitrogen of lidocaine with an aminoethyl group increased the potency and improved the therapeutic index over the corresponding secondary amides when tested in mice.

=References=
#{{ Citation| last=McMaster
| first=Paul D.
| last2=Byrnes
| first2=Eugene W.
| last3=Block
| first3=Alan J.
| last4=Tenthorey
| first4=Paul A.
| title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents
| journal=J. Med. Chem.
| volume=24
| issue=1
| year=1981
| pages=53-58
| url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

It07:Lignocaine

2007-11-01T20:10:34Z

Hjs106: removed extra Jmol image

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, Xylocaine, Xylocard
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| {{{SMILES}}}
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| {{{CASNo}}}
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug known as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

=Potency of Lidocaine=
Substituting the amide nitrogen of lidocaine with an aminoethyl group increased the potency and improved the therapeutic index over the corresponding secondary amides when tested in mice.

=References=
#{{ Citation| last=McMaster
| first=Paul D.
| last2=Byrnes
| first2=Eugene W.
| last3=Block
| first3=Alan J.
| last4=Tenthorey
| first4=Paul A.
| title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents
| journal=J. Med. Chem.
| volume=24
| issue=1
| year=1981
| pages=53-58
| url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

Wikipedia:Sandbox

2007-11-01T16:35:53Z

Hjs106: /* References */

=References=
#{{|last=McMaster|first=Paul D.|last2=Byrnes|first2=Eugene W.|last3=Block|first3=Alan J.|last4=Tenthorey|first4=Paul A.|title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents|journal=J. Med. Chem.|volume=24|issue=1|year=1981|pages=53-58|url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

Wikipedia:Sandbox

2007-11-01T16:35:38Z

Hjs106: /* References */

=References=
#{{Citation|last=McMaster|first=Paul D.|last2=Byrnes|first2=Eugene W.|last3=Block|first3=Alan J.|last4=Tenthorey|first4=Paul A.|title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents|journal=J. Med. Chem.|volume=24|issue=1|year=1981|pages=53-58|url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

Wikipedia:Sandbox

2007-11-01T16:34:37Z

Hjs106:

=References=
#{{Citation| last=McMaster
| first=Paul D.
| last2=Byrnes
| first2=Eugene W.
| last3=Block
| first3=Alan J.
| last4=Tenthorey
| first4=Paul A.
| title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents
| journal=J. Med. Chem.
| volume=24
| issue=1
| year=1981
| pages=53-58
| url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

It07:Lignocaine

2007-11-01T16:32:45Z

Hjs106: Potency of Lidociane, Added References section

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, Xylocaine, Xylocard
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| {{{SMILES}}}
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| {{{CASNo}}}
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug known as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 675 375 150 0 0 0 0 0 5; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

=Potency of Lidocaine=
Substituting the amide nitrogen of lidocaine with an aminoethyl group increased the potency and improved the therapeutic index over the corresponding secondary amides when tested in mice.

=References=
#{{ Citation| last=McMaster
| first=Paul D.
| last2=Byrnes
| first2=Eugene W.
| last3=Block
| first3=Alan J.
| last4=Tenthorey
| first4=Paul A.
| title=New Antiarrhytmic Agents 5. a-Aminoaceto-2,6-xylidides with Functionalized Amide Alkyl Substituents
| journal=J. Med. Chem.
| volume=24
| issue=1
| year=1981
| pages=53-58
| url=http://pubs.acs.org/cgi-bin/archive.cgi/jmcmar/1981/24/i01/pdf/jm00133a012.pdf
}} .

It07:Lignocaine

2007-11-01T15:01:37Z

Hjs106: Added picture of Lidocaine

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Lidocaine.jpg|2D Representation of Lidocaine]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, Xylocaine, Xylocard
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| {{{SMILES}}}
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| {{{CASNo}}}
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug know as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 675 375 150 0 0 0 0 0 5; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

File:Lidocaine.jpg

2007-11-01T14:58:52Z

Hjs106:

File:Lidocaine.JPG

2007-11-01T14:56:23Z

Hjs106:

It07:Lignocaine

2007-11-01T14:48:14Z

Hjs106: Added to to introduction

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Lignocaine.jpg|200px|]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

|-
| Other names
| Lignocaine, Xylocaine, Xylocard
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| {{{SMILES}}}
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| {{{CASNo}}}
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug know as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests. Its large success is largely attributed to its low neurotoxicity compared to many other local anaesthetics. [http://www.appdrugs.com/ Abraxis Pharmaceutical Products] markets Lidocaine under the brand names of '''''Xylocaine''''' and '''''Xylocard'''''.

Jmol 3D structural views of molecule:

<jmol>
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<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 675 375 150 0 0 0 0 0 5; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
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</jmol>

=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

It07:Lignocaine

2007-11-01T14:19:52Z

Hjs106: Removed line: Main Contents page: The wiki project contents page; NOT THE MAIN PAGE

== Lignocaine ==

<noinclude>

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{chembox header}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:It07-Lignocaine.jpg|200px|]]
|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| {{{IUPACName}}}

|-
| Other names
| Lignocaine
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C14H22N2O
|-
| [http://en.wikipedia.org/wiki/Chemical_file_format SMILES] 
| {{{SMILES}}}
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 234.17 gmol-1
|-
| Appearance
| {{{Appearance}}}
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| {{{CASNo}}}
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Density Density] & [http://en.wikipedia.org/wiki/Phase_%28matter%29 phase]
| {{{Density}}} g/cm³ 
|-
| [http://en.wikipedia.org/wiki/Solubility Solubility in water]
| {{{Sol_Water}}} g/100 ml (25°C) 
|-



| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 339-342 K 
|-
| [http://en.wikipedia.org/wiki/Boiling_point Boiling point]
| {{{Bp}}} K
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Acidity] (p''K''a) 
| {{{pKa}}}
|-
| [http://en.wikipedia.org/wiki/Acid_dissociation_constant Basicity] (p''K''b) 
| {{{pKb}}}
|-
| [http://en.wikipedia.org/wiki/Specific_rotation Chiral rotation <nowiki>[α]</nowiki>D] 
| {{{Rotation}}}°
|-
| [http://en.wikipedia.org/wiki/Viscosity Viscosity]
| {{{Viscosity}}} [[Poise|cP]] at 25°C 
|-
! {{chembox header}} | Structure
|-
| [http://en.wikipedia.org/wiki/Orbital_hybridisation Molecular shape] 
| {{{Mol_Shape}}} 
|-
| [http://en.wikipedia.org/wiki/Coordination_geometry Coordination geometry] 
| {{{Coordination}}} 
|-
| [http://en.wikipedia.org/wiki/Crystal_structure Crystal structure] 
| {{{Crystal_Structure}}} 
|-
| [[Dipole#Molecular_dipoles|Dipole moment]]
| {{{DM}}} [[Debye|D]]
|-
! {{chembox header}} | Hazards 
|-
| [[Material safety data sheet|MSDS]]
| [[{{PAGENAME}} (data page)#Material Safety Data Sheet|External MSDS]] 
|-
| Main [[Worker safety and health|hazard]]s
| {{{Hazards}}} 
|-
| [[NFPA 704]]
| {{{NFPA}}}
|-
| [[Flash point]]
| {{{Fp}}}°C
|-
| [[Risk and Safety Statements|R/S statement]]
| [[List of R-phrases|R]]: {{{R-S}}} [[List of S-phrases|S]]: ?
|-
| [[RTECS]] number
| {{{RTECS}}}
|-
! {{chembox header}} | [[{{PAGENAME}} (data page)|Supplementary data page]]
|-
| [[{{PAGENAME}} (data page)#Structure and properties|Structure and properties]]
| [http://en.wikipedia.org/wiki/Refractive_index ''n''], [http://en.wikipedia.org/wiki/Dielectric_constant εr], etc.
|-
| [[{{PAGENAME}} (data page)#Thermodynamic properties|Thermodynamic data]]
| Phase behaviour Solid, liquid, gas
|-
| [[{{PAGENAME}} (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[nuclear magnetic resonance spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Other [[Ion|anion]]s 
| {{{Other_anion}}} 
|-
| Other [[Ion|cation]]s 
| {{{Ohter_cation}}} 
|-
| Related compounds

| {{{Relative_Compounds}}}
|-
| {{chembox header}} | Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25 °C, 100 kPa)]] [[wikipedia:Chemical infobox|Infobox disclaimer and references]]
|-
|}
{{Chem-Data_Structure}}

Lignocaine is the British Approved Name of the drug know as Lidocaine under its International Nonproprietary Name. It was the first type of amino amide-type local anaesthetic in medicine. Developed first by the Swedish scientists Nils Löfgren and Bengt Lundqvist in 1943, it was marketed in 1948 after extensive tests.

Jmol 3D structural views of molecule:

<jmol>
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<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 620 300 120 0 0 0 0 0 4; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
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AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
</jmolApplet>
</jmol>

<jmol>
<jmolApplet>
<size>500</size>
<color>black</color>
<script>zoom 110;frame 1; move 675 375 150 0 0 0 0 0 5; delay 1;</script>
<inlineContents>HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 2.775 1.116 -0.266 0.00 0.00 C+0
ATOM 2 C 0 2.405 2.513 -0.693 0.00 0.00 C+0
ATOM 3 C 0 4.016 0.868 0.289 0.00 0.00 C+0
ATOM 4 C 0 4.356 -0.413 0.681 0.00 0.00 C+0
ATOM 5 C 0 3.456 -1.451 0.519 0.00 0.00 C+0
ATOM 6 C 0 2.215 -1.210 -0.035 0.00 0.00 C+0
ATOM 7 C 0 1.235 -2.341 -0.211 0.00 0.00 C+0
ATOM 8 C 0 1.868 0.077 -0.424 0.00 0.00 C+0
ATOM 9 N 0 0.610 0.325 -0.986 0.00 0.00 N+0
ATOM 10 C 0 -0.507 0.033 -0.291 0.00 0.00 C+0
ATOM 11 O 0 -0.426 -0.536 0.777 0.00 0.00 O+0
ATOM 12 C 0 -1.858 0.414 -0.841 0.00 0.00 C+0
ATOM 13 N 0 -2.906 -0.010 0.097 0.00 0.00 N+0
ATOM 14 C 0 -2.892 0.950 1.208 0.00 0.00 C+0
ATOM 15 C 0 -3.663 0.368 2.394 0.00 0.00 C+0
ATOM 16 C 0 -4.189 0.165 -0.597 0.00 0.00 C+0
ATOM 17 C 0 -4.384 -0.971 -1.604 0.00 0.00 C+0
ATOM 18 H 0 2.775 2.694 -1.702 0.00 0.00 H+0
ATOM 19 H 0 1.321 2.622 -0.677 0.00 0.00 H+0
ATOM 20 H 0 2.853 3.233 -0.007 0.00 0.00 H+0
ATOM 21 H 0 4.721 1.677 0.417 0.00 0.00 H+0
ATOM 22 H 0 5.327 -0.604 1.115 0.00 0.00 H+0
ATOM 23 H 0 3.725 -2.451 0.826 0.00 0.00 H+0
ATOM 24 H 0 0.574 -2.388 0.655 0.00 0.00 H+0
ATOM 25 H 0 0.643 -2.173 -1.111 0.00 0.00 H+0
ATOM 26 H 0 1.778 -3.281 -0.304 0.00 0.00 H+0
ATOM 27 H 0 0.542 0.706 -1.875 0.00 0.00 H+0
ATOM 28 H 0 -1.904 1.495 -0.973 0.00 0.00 H+0
ATOM 29 H 0 -2.010 -0.077 -1.802 0.00 0.00 H+0
ATOM 30 H 0 -1.862 1.147 1.505 0.00 0.00 H+0
ATOM 31 H 0 -3.363 1.881 0.890 0.00 0.00 H+0
ATOM 32 H 0 -3.144 -0.514 2.768 0.00 0.00 H+0
ATOM 33 H 0 -3.728 1.114 3.187 0.00 0.00 H+0
ATOM 34 H 0 -4.668 0.091 2.074 0.00 0.00 H+0
ATOM 35 H 0 -5.000 0.149 0.131 0.00 0.00 H+0
ATOM 36 H 0 -4.191 1.120 -1.122 0.00 0.00 H+0
ATOM 37 H 0 -3.530 -1.007 -2.280 0.00 0.00 H+0
ATOM 38 H 0 -4.466 -1.918 -1.071 0.00 0.00 H+0
ATOM 39 H 0 -5.294 -0.796 -2.177 0.00 0.00 H+0
CONECT 1 8 2 3 0 NONE 44
CONECT 2 1 18 19 20 NONE 45
CONECT 3 1 4 21 0 NONE 46
CONECT 4 3 5 22 0 NONE 47
CONECT 5 4 6 23 0 NONE 48
CONECT 6 5 7 8 0 NONE 49
CONECT 7 6 24 25 26 NONE 50
CONECT 8 6 1 9 0 NONE 51
CONECT 9 8 10 27 0 NONE 52
CONECT 10 9 11 12 0 NONE 53
CONECT 11 10 0 0 0 NONE 54
CONECT 12 10 13 28 29 NONE 55
CONECT 13 12 14 16 0 NONE 56
CONECT 14 13 15 30 31 NONE 57
CONECT 15 14 32 33 34 NONE 58
CONECT 16 13 17 35 36 NONE 59
CONECT 17 16 37 38 39 NONE 60
END NONE 61</inlineContents>
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=Uses=
Lignocaine is a common local anaesthetic, injected as a dental anaesthetic and in minor surgery. It can also come in the form of an ointment as an antiarrhythmic to relieve itching, burning and pain from skin inflammations.

=Side effects=
It is rare to have any side effects caused by Lignocaine; however, allergic reactions can occur. Toxicity occurs for two reasons: either unintended intravascular administration, or administration of an excessive dose.

When excessive quantities of Lignocaine are used, the central nervous system and cardiovascular system may be affected. CNS effects may include CNS excitation such as nervousness, tingling around the mouth, tremors, blurred vision, seizure, followed by depression - drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmia, and cardiac arrest.

When Lidocaine is used as a local anaesthetic for regional nerve blocks, the plasma levels are usually at about 3-5 mcg/mL. Toxic effects of the Lidocaine can be detected when the plasma level is at 6 mcg/mL, but are common when the plasma levels exceed 10 mcg/mL.
Although the quantity of dose is the major factor, there are several others that modulate the degree of toxicity. These include the relative vascularity of the injection site, and coincidentally the speed of the injection of the anaesthetic. Lidocaine is hepatically metabolized; this will increase the chance of liver dysfunction, which will in turn increase the risk of toxic effects. Being bound within a protein, when low protein states are encountered there is also a possibility that the toxicity will increase. The biological process of ‘acidosis’ increases the risk of toxicity, as it favours the dissociation of Lidocaine from the plasma proteins.
Further medication can lead to interactions with anaesthetic, thus leading to increased toxicity as the level of Lidocaine is affected. Common medications with a chance of such reaction include: cimetidine, ciprofloxacin, clonidine, phenytoin, and beta-blockers such as propranolol, metoprolol, and nadolol.

=How does it work?=
Lidocaine works by changing the depolarisation in neurons. It achieves this by preventing the voltage gated sodium ion channel in the neuron’s axon cell membrane from functioning. When a threshold number of channels are blocked, the membrane will no longer be able to depolarise, therefore be unable to transmit an action potential. This inability leads to the molecule’s anaesthetic effect.

It07:Mefloquine

2007-11-01T13:08:24Z

Hjs106: edited: transmitted for administered. (administration of drugs rather than transmition)

===Mefloquine (Lariam)===
{{Drug-Box |
| Box_Name = Mefloquine
| ImageFile = [[Image:lariam.png]]
| IUPACName = 2,8-bis(trifluoromethyl)quinolin-4-yl]-(2-piperidyl)methanol
| OtherName = Lariam, mephaquin
| CASNo = 53230-10-7
| ATC_Code = P01BC02
| PubChem = 4046
| SMILES = <nowiki>FC(F)(F)C1=CC=CC2=C1N=C(C(F)(F)F)C=C2C(O[H])C3N([H])CCCC3</nowiki>
| Formula = C17H16F6N2O
| MolarMass = 378.312 g/mol
| Bioavailability = <85%
| Protein_binding =
| Metabolism = vast majority is hepatic
| Half_life = 305.3hrs
| Excretion = Mostly via the faeces and bile. Urinal excretion composed of 9% unchanged mefloquine; 4% main metabolite
| Pregnancy_cat = C (US)
| Legal_status =
| Routes = Oral
}}

Mefloquine, better known as Lariam (produced by Hoffman La-Roche pharmaceuticals) is an orally-administered drug that is used for treatment, as well as a prophylactic measure against malaria. It was developed in the 1970's in the Walter Reed Army Institute of Research, USA, as a synthetic analog of the naturally-occuring molecule,[http://en.wikipedia.org/wiki/Quinine/ quinine]
(found naturally in the Peruvian cinchona tree).

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==A short overview on Malaria==
Malaria is transmitted from person to person, by female anopheles genus mosquitoes that are infected with the plasmodium parasite. This parasite then multiplies and matures in the liver before reentering the blood stream and attacking red blood cells. Malaria is widespread in tropical and subtropical regions, where the climate is favourable for the breeding of this mosquito.

[[Image:Malariacycle2.jpg]]''Taken from www.traveldoctor.co.uk/malaria.htm''

Symptoms include: fever, shivering, vomiting, joint poin, amaemia, convulsions, haemolysis (caused by the lysing of the red blood cells)and haemoglobinuria (this is when excess haemoglobin is excreted via the kidneys).

''This is a map of where malaria is commonly found:''

[[Image:malaria map.gif]]

''Taken from http://www.malariahotspots.co.uk/files/images/MH_L1_facts_map.gif''

== Physical Properties ==
Mefloquine is a white- white crystalline solid that is slightly soluble in water. It is derived from 4-quinolinemethol and has the specific chemical name of (R*,S*)-(+_)-α-2-piperidinnyl-2,8-bis(trifluoromethyl)-4quinolinemethanol hydrochloride. Mefloquine hydroxide is a chiral molecule and the drug contains both of these enantiomers. It is still not known whether there is stearic switching after the drug has been consumed. It has been found, however that not only does the (-) enantiomer have a shorter halflife, but it also binds to the adenosine receptors in the central nervous system, which may explain some adverse side-effects of the drug.

== More about the Drug ==
Mefloquine is a schizonticide- a drug that selectively targets a certain sporazoan parasite. The exact mechanism of this remains unknown. It is classified within the quinine family that also includes Chloroquine, quinine, quinidine and Hydroxychlorquine. Mefloquine is effective when treating chloroquine-resistant strains of malaria and is active during the time the parasite is in the blood (erythrocytic period). However, it has no effect during the hepatic stages of the illness.

==Mefloquine Resistance==
The parasite responsible for malaria is growing ever-more resistant to antimalarial drugs, which makes treatment and prevention more difficult. Strains of the parasite with increased resistance to mefloquine have been found in South East Asia, notably in Myanmar, Thailand and Cambodia, as well as incresingly in other parts of the world. Cross resistance of mefloquine and quinine, as well as mefloquine and halofantrine (a non-prophylactic antimalarial drug that is only used in treatment) has also been observed in other regions. Treating drug-resistant malaria requires a mixture of different treatments.

[[Image:MalariaMap.gif]]

''From www.traveldoctor.co.uk/malaria.htm''