ChemWiki - User contributions [en]

It07:Lignocaine

2007-10-23T15:11:36Z

Bbwt05: /* Uses */

== Lignocaine ==

Main Contents page: [[It:projects|The wiki project contents page; NOT THE MAIN PAGE]]

<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 it's International Nonproprietary Name.

Jmol 3d Structural views of molecule.

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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>
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<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 that can be injected as a dental anaesthetic and in minor surgery. It can also come in 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. When excessive quantities of lignocaine is used, the central nervous system and cardiovascular system may be effected. CNS effects may include CNS excitation such as nervousness, tingling aroudn the mouth, tremor, blurred vision, seizure, followed by depression, eg. drowsiness, loss of consciousness, respiratory depression and apnea. Cardiovascular effects include hypotension, bradycardia, arrhythmias and cardiac arrest.

It07:Lignocaine

2007-10-23T15:07:12Z

Bbwt05: /* Uses */

It07:Lignocaine

2007-10-23T15:00:45Z

Bbwt05: /* Lignocaine */

It07:Gossypol

2007-10-23T14:33:45Z

Bbwt05: /* Uses and Side Effects */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

<jmol>
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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>
</jmolApplet>
</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

=Uses and Side Effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organiszation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.1

Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis2 is also known that familial paralysis and occurs due to low levels of potassium in the body. During an attack of paralysis, muschle weakness results in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal.

Also, recovery of those who used gossypol is only 75% and can lead to other related symptoms like smaller testicular colume, and elevated follicle stimulating hormone concentrations.1

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

*1)http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=9639146&dopt=Citation
*2)http://www.clevelandclinic.org/health/health-info/docs/2400/2452.asp?index=9499
http://www.emolecules.com/cgi-bin/more?vid=538892#

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

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

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

It07:Gossypol

2007-10-23T14:33:31Z

Bbwt05: /* Uses and Side Effects */

It07:Gossypol

2007-10-23T14:32:58Z

Bbwt05: /* References */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<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>
</jmolApplet>
</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

=Uses and Side Effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organiszation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.1
Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis2 is also known that familial paralysis and occurs due to low levels of potassium in the body. During an attack of paralysis, muschle weakness results in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal.
Also, recovery of those who used gossypol is only 75% and can lead to other related symptoms like smaller testicular colume, and elevated follicle stimulating hormone concentrations.1

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

*1)http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=9639146&dopt=Citation
*2)http://www.clevelandclinic.org/health/health-info/docs/2400/2452.asp?index=9499
http://www.emolecules.com/cgi-bin/more?vid=538892#

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

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

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

It07:Gossypol

2007-10-23T14:31:03Z

Bbwt05: /* Uses and effects */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<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>
</jmolApplet>
</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

=Uses and Side Effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organiszation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.1
Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis2 is also known that familial paralysis and occurs due to low levels of potassium in the body. During an attack of paralysis, muschle weakness results in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal.
Also, recovery of those who used gossypol is only 75% and can lead to other related symptoms like smaller testicular colume, and elevated follicle stimulating hormone concentrations.1

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

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

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

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

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

It07:Gossypol

2007-10-23T14:21:52Z

Bbwt05: /* History */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<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>
</jmolApplet>
</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

=Uses and effects=

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

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

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

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

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

It07:Gossypol

2007-10-23T14:21:27Z

Bbwt05: /* History */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<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>
</jmolApplet>
</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

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

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

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

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

It07:Gossypol

2007-10-23T14:21:09Z

Bbwt05: /* Uses and effects */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<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>
</jmolApplet>
</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

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

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

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

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

It07:Gossypol

2007-10-23T14:18:39Z

Bbwt05: /* History */

{{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 =
| 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 =
}}

Gossypol, C30H30O8, (IUPAC 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) is a pigment named after the species of cotton, ''Gossypium L., Malvaceae'', that bears the seeds from which it is extracted. Initially it was known only as an undesirable toxin found in cotton-oil containing food-stuffs, 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 (see history subheading).
(source; Merck Index)

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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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</jmol>

= 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. This 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 and affects more than 1 million Britains. (Source; BBC article)

=Uses and effects=

= 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. (source; Merck Index)

A large scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects. Hypokalemia is where there is low levels of potassium in the blood which effects the transmission between muscles and nerves. Scientists tried to remedy this by giving male monkeys gossypol along with a daily potassium tablet however this did not work. Therefore hypokalemia is an evitable side effect.

A man who uses the drug could become partially if not fully infertile the longer they used the drug.

= References =

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

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

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

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

It07:h3nbh3

2007-10-23T14:09:00Z

Bbwt05: /* References */

==Ammonia-borane==

Ammonia-borane has the following structure:

[[Image:screen_cap_ammonia_borane_2.jpg]] Point group = C3V

Right click on molecule to explore.
SMILES: [H][N@@]([H])([H])[B@]([H])([H])[H]

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HEADER CSD ENTRY FUYVUQ01
CRYST1 5.4210 4.9450 5.0230 90.00 90.00 90.00 Pmn21
SCALE1 0.184468 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.202224 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.199084 0.000000
HETATM 1 B1 UNK 1 -0.000 -0.946 0.000 1.00 0.00 B
HETATM 2 H1 UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 3 H2 UNK 1 0.000 0.237 0.141 1.00 0.00 H
HETATM 4 N1 UNK 1 -0.000 -1.172 -1.585 1.00 0.00 N
HETATM 5 H3 UNK 1 -0.000 -1.879 -1.793 1.00 0.00 H
HETATM 6 H4 UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
HETATM 7 H1B UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 8 H4B UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 9 H1 UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 10 H4 UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 11 H1B UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 12 H4B UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 1 9 11
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 4 10 12
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 1
CONECT 10 4
CONECT 11 1
CONECT 12 4
MASTER 0 0 0 0 0 0 0 0 3 12 0 14 0
END
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== Crystal Structure ==
6

3D representation of the crystal unit cell. Right click on image to explore unit cell.

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HEADER CSD ENTRY FUYVUQ02
CRYST1 5.3950 4.8870 4.9860 90.00 90.00 90.00 Pmn21
SCALE1 0.185357 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.204625 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.200562 0.000000
HETATM 1 N1 UNK 1 -0.000 1.148 1.566 1.00 0.00 N
HETATM 2 H1 UNK 1 -0.000 2.214 1.700 1.00 0.00 H
HETATM 3 H2 UNK 1 0.755 0.723 1.979 1.00 0.00 H
HETATM 4 B1 UNK 1 0.000 0.904 0.000 1.00 0.00 B
HETATM 5 H3 UNK 1 -0.000 -0.210 -0.299 1.00 0.00 H
HETATM 6 H4 UNK 1 0.998 1.290 -0.499 1.00 0.00 H
HETATM 7 H2 UNK 1 -0.755 0.723 1.979 1.00 0.00 H
HETATM 8 H4 UNK 1 -0.998 1.290 -0.499 1.00 0.00 H
HETATM 9 N1 UNK 1 5.395 1.148 1.566 1.00 0.00 N
HETATM 10 H1 UNK 1 5.395 2.214 1.700 1.00 0.00 H
HETATM 11 H2 UNK 1 6.150 0.723 1.979 1.00 0.00 H
HETATM 12 B1 UNK 1 5.395 0.904 0.000 1.00 0.00 B
HETATM 13 H3 UNK 1 5.395 -0.210 -0.299 1.00 0.00 H
HETATM 14 H4 UNK 1 6.393 1.290 -0.499 1.00 0.00 H
HETATM 15 H2 UNK 1 4.640 0.723 1.979 1.00 0.00 H
HETATM 16 H4 UNK 1 4.397 1.290 -0.499 1.00 0.00 H
HETATM 17 N1 UNK 1 2.698 3.739 4.059 1.00 0.00 N
HETATM 18 H1 UNK 1 2.698 2.673 4.193 1.00 0.00 H
HETATM 19 H2 UNK 1 1.943 4.164 4.472 1.00 0.00 H
HETATM 20 B1 UNK 1 2.698 3.983 2.493 1.00 0.00 B
HETATM 21 H3 UNK 1 2.698 5.097 2.194 1.00 0.00 H
HETATM 22 H4 UNK 1 1.700 3.597 1.994 1.00 0.00 H
HETATM 23 H2 UNK 1 3.453 4.164 4.472 1.00 0.00 H
HETATM 24 H4 UNK 1 3.695 3.597 1.994 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 10 11 12 15
CONECT 10 9
CONECT 11 9
CONECT 12 9 13 14 16
CONECT 13 12
CONECT 14 12
CONECT 15 9
CONECT 16 12
CONECT 17 18 19 20 23
CONECT 18 17
CONECT 19 17
CONECT 20 17 21 22 24
CONECT 21 20
CONECT 22 20
CONECT 23 17
CONECT 24 20
MASTER 0 0 0 0 0 0 0 0 3 24 0 24 0
END

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All cell parameter values in Å.
Method used to determine unit cell details is neutron diffraction
[[Image:screen_cap_crystal_cell.jpg]]

==Synthesis==

High purity (98%) and high yields (>95%) of ammonia borane can be achieved with reactions involving the direct addition of ammonium salts and sodium borohydride. 1

Ammonia borane can be synthesised by direct reaction of BH3(THF) and ammonia:
BH3(THF) + NH3 --> BH3NH3
The main product in this reaction is ammonia-borane.

===Other synthetic routes===

* Diborane + bisamminedihydroboriumtetrahydroborate --> ammonia-borane 2

Solvent: diglyme, Note: Slow reaction

*Ammodiumamidosulfonat + natrium boron hydride --> ammonia borane + H2 + NaNH2SO3 3

Solvent: liquid ammonia + ether, Purification/Isolation: solution was allowed to warm to room temperature; filtered; ether evaporated.

* Ammonium Chloride + Lithium Borohydride ---> ammonia borane + H2 4

Byproduct: LiCl

* Borane methylsulfide + ammonia --> ammonia borane + bisamminedihydroboriumtetrahydroborate 5

Solvent: No solvent required , General conditions: -20oC , Purification/Isolation: Recrystallisation from ether

==Uses and applications==

Ammonia borane is becoming an increasingly interesting molecule for hydrogen storage. It has found uses in applications such as motor vehicles and power generators in portable devices. Ammonia borane can hold large quantities of hydrogen but is not easily reversible. Part of the reason for this irreversibility is due to entropic reasons. When ammonia boarane is heated it decomposes into hydrogen gas and a few other compounds depending on conditions; as a result hydrogen can be readily evolved but the process cannot be easily reversed to recycle any unused hydrogen for later usage. Approximately one millilitre of ammonia borane can produce up to 1.8 litres of hydrogen gas. 10

Another advantage of using ammonia borane as hydrogen storage as opposed to hydrogen gas is because it has a melting point at -34 degrees Celsius, which is a lot higher than that of hydrogen. Also, ammonia borane becomes liquid at room temperature at 9 atmospheres pressure, this makes it much more convenient to use as a transportation fuel.11

Ammonia borane has also found many uses in organic synthesis, replacing diborane due to it being stable in air.

==Properties of Ammonia-borane==

===Bond Lengths===

*B-N: 1.58 Å
*B-H: 1.15 Å
*N-H: 0.96 Å

===Physical Properties===

*Appearance: Colourless, waxy solid
*Melting point: 104oC
*Boiling point: Decomposes
*Solubility in water: Good
*Decomposition: 80oC 7
*Ionization potential (Photoelectron spectroscopy [vertical]): 10.33eV-10.9eV 8

Ammonia-borane dissolves well in water due to the strong ionic component in the N-B bond given that there is a significant difference in the pauling electronegativity ( 3.04[N]-2.04[B]=1) between nitrogen and boron. This means that water molecules can easily solvate ammonia-borane as there is a strong attractive component between the permanent dipoles on the water molecules and the B-N bond in ammonia-borane.

*Density: 0.780 g/cm3
*Crystal structure: 14mm (tetragonal, >200K)
*Dipole moment: 5.2D 9

The dipole moment of ammonia borane arises due to the large difference in pauling electronegativity (as discussed with the solubility in water). Water has a dipole moment of 1.85D; therefore ammonia borane's dipole moment is approximately 3 times as much. To compare, this explains why water is a liquid in room temperature and pressure while ammonia borane is a solid due to the strong dipole-dipole interactions.

===Stability===

Ammonia borane is stable at room temperature and can last for hours when placed in aqueous solution. However, it decomposes rapidly when the compound is added to liquid ammonia or ether after addition of water. The molecule is also stable in anhydrous ether or liquid ammonia.

==Hazards==
*Flammable / keep away from heat
*Explosive (Heating causes ammonia borane to decompose into hydrogen gas!)
*Toxic if swallowed. 12
*Harmful by inhalation. 12
*Irritating to eyes.12

==References==

*1)http://pubs.acs.org/cgi-bin/abstract.cgi/inocaj/2007/46/i19/abs/ic700772a.html
*2)Mayer E, Inorg. chem, vol 12, 1973, Pg 1954-1952 {{doi-inline|doi:10.1021/ic50126a060|reference}}
*3)Thorne L R , Chem Phys Lett, vol 78, 1981, pg157-160 {{doi-inline|doi:10.1016/0009-2614(81)85575-3|reference}}
*4)Parry R W, J.am.chem.soc, vol 77, 1955, pg 2072-2074
*5)Adams R M, Inorg. Chem, vol 10, 1971, pg 2072-2074
*6) W T Klooster, J.Am.Chem.Soc., vol 121, 1999, pg 6337 {{doi-inline|doi:10.10121/ja9825332|reference}}
*7) Tubyanskaya V.S, Zh.fiz.khim, vol 40, 1966, pg 122-124
*8) Lloyd D.R, J.chem.soc.D, 1970, pg 1545-1546
*9) Crabtree Robert H, J.am.chem.soc, vol 121, 1999, 6333-6343
*10) http://biopact.com/2007/08/storing-hydrogen-in-solid-ammonia.html
*11) http://www.americanscientist.org/template/AssetDetail/assetid/45942
*12)http://www.americanscientist.org/template/AssetDetail/assetid/45942

It07:h3nbh3

2007-10-23T14:08:26Z

Bbwt05: /* Hazards */

It07:h3nbh3

2007-10-23T14:07:51Z

Bbwt05: /* Hazards */

==Ammonia-borane==

Ammonia-borane has the following structure:

[[Image:screen_cap_ammonia_borane_2.jpg]] Point group = C3V

Right click on molecule to explore.
SMILES: [H][N@@]([H])([H])[B@]([H])([H])[H]

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>correct_conformation.ent
HEADER CSD ENTRY FUYVUQ01
CRYST1 5.4210 4.9450 5.0230 90.00 90.00 90.00 Pmn21
SCALE1 0.184468 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.202224 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.199084 0.000000
HETATM 1 B1 UNK 1 -0.000 -0.946 0.000 1.00 0.00 B
HETATM 2 H1 UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 3 H2 UNK 1 0.000 0.237 0.141 1.00 0.00 H
HETATM 4 N1 UNK 1 -0.000 -1.172 -1.585 1.00 0.00 N
HETATM 5 H3 UNK 1 -0.000 -1.879 -1.793 1.00 0.00 H
HETATM 6 H4 UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
HETATM 7 H1B UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 8 H4B UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 9 H1 UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 10 H4 UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 11 H1B UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 12 H4B UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 1 9 11
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 4 10 12
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 1
CONECT 10 4
CONECT 11 1
CONECT 12 4
MASTER 0 0 0 0 0 0 0 0 3 12 0 14 0
END
</inlineContents>
</jmolApplet>
</jmol>

== Crystal Structure ==
6

3D representation of the crystal unit cell. Right click on image to explore unit cell.

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>FUYVUQ02correct.ent
HEADER CSD ENTRY FUYVUQ02
CRYST1 5.3950 4.8870 4.9860 90.00 90.00 90.00 Pmn21
SCALE1 0.185357 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.204625 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.200562 0.000000
HETATM 1 N1 UNK 1 -0.000 1.148 1.566 1.00 0.00 N
HETATM 2 H1 UNK 1 -0.000 2.214 1.700 1.00 0.00 H
HETATM 3 H2 UNK 1 0.755 0.723 1.979 1.00 0.00 H
HETATM 4 B1 UNK 1 0.000 0.904 0.000 1.00 0.00 B
HETATM 5 H3 UNK 1 -0.000 -0.210 -0.299 1.00 0.00 H
HETATM 6 H4 UNK 1 0.998 1.290 -0.499 1.00 0.00 H
HETATM 7 H2 UNK 1 -0.755 0.723 1.979 1.00 0.00 H
HETATM 8 H4 UNK 1 -0.998 1.290 -0.499 1.00 0.00 H
HETATM 9 N1 UNK 1 5.395 1.148 1.566 1.00 0.00 N
HETATM 10 H1 UNK 1 5.395 2.214 1.700 1.00 0.00 H
HETATM 11 H2 UNK 1 6.150 0.723 1.979 1.00 0.00 H
HETATM 12 B1 UNK 1 5.395 0.904 0.000 1.00 0.00 B
HETATM 13 H3 UNK 1 5.395 -0.210 -0.299 1.00 0.00 H
HETATM 14 H4 UNK 1 6.393 1.290 -0.499 1.00 0.00 H
HETATM 15 H2 UNK 1 4.640 0.723 1.979 1.00 0.00 H
HETATM 16 H4 UNK 1 4.397 1.290 -0.499 1.00 0.00 H
HETATM 17 N1 UNK 1 2.698 3.739 4.059 1.00 0.00 N
HETATM 18 H1 UNK 1 2.698 2.673 4.193 1.00 0.00 H
HETATM 19 H2 UNK 1 1.943 4.164 4.472 1.00 0.00 H
HETATM 20 B1 UNK 1 2.698 3.983 2.493 1.00 0.00 B
HETATM 21 H3 UNK 1 2.698 5.097 2.194 1.00 0.00 H
HETATM 22 H4 UNK 1 1.700 3.597 1.994 1.00 0.00 H
HETATM 23 H2 UNK 1 3.453 4.164 4.472 1.00 0.00 H
HETATM 24 H4 UNK 1 3.695 3.597 1.994 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 10 11 12 15
CONECT 10 9
CONECT 11 9
CONECT 12 9 13 14 16
CONECT 13 12
CONECT 14 12
CONECT 15 9
CONECT 16 12
CONECT 17 18 19 20 23
CONECT 18 17
CONECT 19 17
CONECT 20 17 21 22 24
CONECT 21 20
CONECT 22 20
CONECT 23 17
CONECT 24 20
MASTER 0 0 0 0 0 0 0 0 3 24 0 24 0
END

</inlineContents>
</jmolApplet>
</jmol>

All cell parameter values in Å.
Method used to determine unit cell details is neutron diffraction
[[Image:screen_cap_crystal_cell.jpg]]

==Synthesis==

High purity (98%) and high yields (>95%) of ammonia borane can be achieved with reactions involving the direct addition of ammonium salts and sodium borohydride. 1

Ammonia borane can be synthesised by direct reaction of BH3(THF) and ammonia:
BH3(THF) + NH3 --> BH3NH3
The main product in this reaction is ammonia-borane.

===Other synthetic routes===

* Diborane + bisamminedihydroboriumtetrahydroborate --> ammonia-borane 2

Solvent: diglyme, Note: Slow reaction

*Ammodiumamidosulfonat + natrium boron hydride --> ammonia borane + H2 + NaNH2SO3 3

Solvent: liquid ammonia + ether, Purification/Isolation: solution was allowed to warm to room temperature; filtered; ether evaporated.

* Ammonium Chloride + Lithium Borohydride ---> ammonia borane + H2 4

Byproduct: LiCl

* Borane methylsulfide + ammonia --> ammonia borane + bisamminedihydroboriumtetrahydroborate 5

Solvent: No solvent required , General conditions: -20oC , Purification/Isolation: Recrystallisation from ether

==Uses and applications==

Ammonia borane is becoming an increasingly interesting molecule for hydrogen storage. It has found uses in applications such as motor vehicles and power generators in portable devices. Ammonia borane can hold large quantities of hydrogen but is not easily reversible. Part of the reason for this irreversibility is due to entropic reasons. When ammonia boarane is heated it decomposes into hydrogen gas and a few other compounds depending on conditions; as a result hydrogen can be readily evolved but the process cannot be easily reversed to recycle any unused hydrogen for later usage. Approximately one millilitre of ammonia borane can produce up to 1.8 litres of hydrogen gas. 10

Another advantage of using ammonia borane as hydrogen storage as opposed to hydrogen gas is because it has a melting point at -34 degrees Celsius, which is a lot higher than that of hydrogen. Also, ammonia borane becomes liquid at room temperature at 9 atmospheres pressure, this makes it much more convenient to use as a transportation fuel.11

Ammonia borane has also found many uses in organic synthesis, replacing diborane due to it being stable in air.

==Properties of Ammonia-borane==

===Bond Lengths===

*B-N: 1.58 Å
*B-H: 1.15 Å
*N-H: 0.96 Å

===Physical Properties===

*Appearance: Colourless, waxy solid
*Melting point: 104oC
*Boiling point: Decomposes
*Solubility in water: Good
*Decomposition: 80oC 7
*Ionization potential (Photoelectron spectroscopy [vertical]): 10.33eV-10.9eV 8

Ammonia-borane dissolves well in water due to the strong ionic component in the N-B bond given that there is a significant difference in the pauling electronegativity ( 3.04[N]-2.04[B]=1) between nitrogen and boron. This means that water molecules can easily solvate ammonia-borane as there is a strong attractive component between the permanent dipoles on the water molecules and the B-N bond in ammonia-borane.

*Density: 0.780 g/cm3
*Crystal structure: 14mm (tetragonal, >200K)
*Dipole moment: 5.2D 9

The dipole moment of ammonia borane arises due to the large difference in pauling electronegativity (as discussed with the solubility in water). Water has a dipole moment of 1.85D; therefore ammonia borane's dipole moment is approximately 3 times as much. To compare, this explains why water is a liquid in room temperature and pressure while ammonia borane is a solid due to the strong dipole-dipole interactions.

===Stability===

Ammonia borane is stable at room temperature and can last for hours when placed in aqueous solution. However, it decomposes rapidly when the compound is added to liquid ammonia or ether after addition of water. The molecule is also stable in anhydrous ether or liquid ammonia.

==Hazards==
*Flammable / keep away from heat
*Explosive (Heating causes ammonia borane to decompose into hydrogen gas!)
*Toxic if swallowed.
*Harmful by inhalation.
*Irritating to eyes.

==References==

*1)http://pubs.acs.org/cgi-bin/abstract.cgi/inocaj/2007/46/i19/abs/ic700772a.html
*2)Mayer E, Inorg. chem, vol 12, 1973, Pg 1954-1952 {{doi-inline|doi:10.1021/ic50126a060|reference}}
*3)Thorne L R , Chem Phys Lett, vol 78, 1981, pg157-160 {{doi-inline|doi:10.1016/0009-2614(81)85575-3|reference}}
*4)Parry R W, J.am.chem.soc, vol 77, 1955, pg 2072-2074
*5)Adams R M, Inorg. Chem, vol 10, 1971, pg 2072-2074
*6) W T Klooster, J.Am.Chem.Soc., vol 121, 1999, pg 6337 {{doi-inline|doi:10.10121/ja9825332|reference}}
*7) Tubyanskaya V.S, Zh.fiz.khim, vol 40, 1966, pg 122-124
*8) Lloyd D.R, J.chem.soc.D, 1970, pg 1545-1546
*9) Crabtree Robert H, J.am.chem.soc, vol 121, 1999, 6333-6343
*10) http://biopact.com/2007/08/storing-hydrogen-in-solid-ammonia.html
*11) http://www.americanscientist.org/template/AssetDetail/assetid/45942

It07:h3nbh3

2007-10-23T14:04:47Z

Bbwt05: /* References */

==Ammonia-borane==

Ammonia-borane has the following structure:

[[Image:screen_cap_ammonia_borane_2.jpg]] Point group = C3V

Right click on molecule to explore.
SMILES: [H][N@@]([H])([H])[B@]([H])([H])[H]

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>correct_conformation.ent
HEADER CSD ENTRY FUYVUQ01
CRYST1 5.4210 4.9450 5.0230 90.00 90.00 90.00 Pmn21
SCALE1 0.184468 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.202224 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.199084 0.000000
HETATM 1 B1 UNK 1 -0.000 -0.946 0.000 1.00 0.00 B
HETATM 2 H1 UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 3 H2 UNK 1 0.000 0.237 0.141 1.00 0.00 H
HETATM 4 N1 UNK 1 -0.000 -1.172 -1.585 1.00 0.00 N
HETATM 5 H3 UNK 1 -0.000 -1.879 -1.793 1.00 0.00 H
HETATM 6 H4 UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
HETATM 7 H1B UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 8 H4B UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 9 H1 UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 10 H4 UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 11 H1B UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 12 H4B UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 1 9 11
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 4 10 12
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 1
CONECT 10 4
CONECT 11 1
CONECT 12 4
MASTER 0 0 0 0 0 0 0 0 3 12 0 14 0
END
</inlineContents>
</jmolApplet>
</jmol>

== Crystal Structure ==
6

3D representation of the crystal unit cell. Right click on image to explore unit cell.

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>FUYVUQ02correct.ent
HEADER CSD ENTRY FUYVUQ02
CRYST1 5.3950 4.8870 4.9860 90.00 90.00 90.00 Pmn21
SCALE1 0.185357 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.204625 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.200562 0.000000
HETATM 1 N1 UNK 1 -0.000 1.148 1.566 1.00 0.00 N
HETATM 2 H1 UNK 1 -0.000 2.214 1.700 1.00 0.00 H
HETATM 3 H2 UNK 1 0.755 0.723 1.979 1.00 0.00 H
HETATM 4 B1 UNK 1 0.000 0.904 0.000 1.00 0.00 B
HETATM 5 H3 UNK 1 -0.000 -0.210 -0.299 1.00 0.00 H
HETATM 6 H4 UNK 1 0.998 1.290 -0.499 1.00 0.00 H
HETATM 7 H2 UNK 1 -0.755 0.723 1.979 1.00 0.00 H
HETATM 8 H4 UNK 1 -0.998 1.290 -0.499 1.00 0.00 H
HETATM 9 N1 UNK 1 5.395 1.148 1.566 1.00 0.00 N
HETATM 10 H1 UNK 1 5.395 2.214 1.700 1.00 0.00 H
HETATM 11 H2 UNK 1 6.150 0.723 1.979 1.00 0.00 H
HETATM 12 B1 UNK 1 5.395 0.904 0.000 1.00 0.00 B
HETATM 13 H3 UNK 1 5.395 -0.210 -0.299 1.00 0.00 H
HETATM 14 H4 UNK 1 6.393 1.290 -0.499 1.00 0.00 H
HETATM 15 H2 UNK 1 4.640 0.723 1.979 1.00 0.00 H
HETATM 16 H4 UNK 1 4.397 1.290 -0.499 1.00 0.00 H
HETATM 17 N1 UNK 1 2.698 3.739 4.059 1.00 0.00 N
HETATM 18 H1 UNK 1 2.698 2.673 4.193 1.00 0.00 H
HETATM 19 H2 UNK 1 1.943 4.164 4.472 1.00 0.00 H
HETATM 20 B1 UNK 1 2.698 3.983 2.493 1.00 0.00 B
HETATM 21 H3 UNK 1 2.698 5.097 2.194 1.00 0.00 H
HETATM 22 H4 UNK 1 1.700 3.597 1.994 1.00 0.00 H
HETATM 23 H2 UNK 1 3.453 4.164 4.472 1.00 0.00 H
HETATM 24 H4 UNK 1 3.695 3.597 1.994 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 10 11 12 15
CONECT 10 9
CONECT 11 9
CONECT 12 9 13 14 16
CONECT 13 12
CONECT 14 12
CONECT 15 9
CONECT 16 12
CONECT 17 18 19 20 23
CONECT 18 17
CONECT 19 17
CONECT 20 17 21 22 24
CONECT 21 20
CONECT 22 20
CONECT 23 17
CONECT 24 20
MASTER 0 0 0 0 0 0 0 0 3 24 0 24 0
END

</inlineContents>
</jmolApplet>
</jmol>

All cell parameter values in Å.
Method used to determine unit cell details is neutron diffraction
[[Image:screen_cap_crystal_cell.jpg]]

==Synthesis==

High purity (98%) and high yields (>95%) of ammonia borane can be achieved with reactions involving the direct addition of ammonium salts and sodium borohydride. 1

Ammonia borane can be synthesised by direct reaction of BH3(THF) and ammonia:
BH3(THF) + NH3 --> BH3NH3
The main product in this reaction is ammonia-borane.

===Other synthetic routes===

* Diborane + bisamminedihydroboriumtetrahydroborate --> ammonia-borane 2

Solvent: diglyme, Note: Slow reaction

*Ammodiumamidosulfonat + natrium boron hydride --> ammonia borane + H2 + NaNH2SO3 3

Solvent: liquid ammonia + ether, Purification/Isolation: solution was allowed to warm to room temperature; filtered; ether evaporated.

* Ammonium Chloride + Lithium Borohydride ---> ammonia borane + H2 4

Byproduct: LiCl

* Borane methylsulfide + ammonia --> ammonia borane + bisamminedihydroboriumtetrahydroborate 5

Solvent: No solvent required , General conditions: -20oC , Purification/Isolation: Recrystallisation from ether

==Uses and applications==

Ammonia borane is becoming an increasingly interesting molecule for hydrogen storage. It has found uses in applications such as motor vehicles and power generators in portable devices. Ammonia borane can hold large quantities of hydrogen but is not easily reversible. Part of the reason for this irreversibility is due to entropic reasons. When ammonia boarane is heated it decomposes into hydrogen gas and a few other compounds depending on conditions; as a result hydrogen can be readily evolved but the process cannot be easily reversed to recycle any unused hydrogen for later usage. Approximately one millilitre of ammonia borane can produce up to 1.8 litres of hydrogen gas. 10

Another advantage of using ammonia borane as hydrogen storage as opposed to hydrogen gas is because it has a melting point at -34 degrees Celsius, which is a lot higher than that of hydrogen. Also, ammonia borane becomes liquid at room temperature at 9 atmospheres pressure, this makes it much more convenient to use as a transportation fuel.11

Ammonia borane has also found many uses in organic synthesis, replacing diborane due to it being stable in air.

==Properties of Ammonia-borane==

===Bond Lengths===

*B-N: 1.58 Å
*B-H: 1.15 Å
*N-H: 0.96 Å

===Physical Properties===

*Appearance: Colourless, waxy solid
*Melting point: 104oC
*Boiling point: Decomposes
*Solubility in water: Good
*Decomposition: 80oC 7
*Ionization potential (Photoelectron spectroscopy [vertical]): 10.33eV-10.9eV 8

Ammonia-borane dissolves well in water due to the strong ionic component in the N-B bond given that there is a significant difference in the pauling electronegativity ( 3.04[N]-2.04[B]=1) between nitrogen and boron. This means that water molecules can easily solvate ammonia-borane as there is a strong attractive component between the permanent dipoles on the water molecules and the B-N bond in ammonia-borane.

*Density: 0.780 g/cm3
*Crystal structure: 14mm (tetragonal, >200K)
*Dipole moment: 5.2D 9

The dipole moment of ammonia borane arises due to the large difference in pauling electronegativity (as discussed with the solubility in water). Water has a dipole moment of 1.85D; therefore ammonia borane's dipole moment is approximately 3 times as much. To compare, this explains why water is a liquid in room temperature and pressure while ammonia borane is a solid due to the strong dipole-dipole interactions.

===Stability===

Ammonia borane is stable at room temperature and can last for hours when placed in aqueous solution. However, it decomposes rapidly when the compound is added to liquid ammonia or ether after addition of water. The molecule is also stable in anhydrous ether or liquid ammonia.

==Hazards==
*Flammable / keep away from heat
*Explosive (Heating causes ammonia borane to decompose into hydrogen gas!)

==References==

*1)http://pubs.acs.org/cgi-bin/abstract.cgi/inocaj/2007/46/i19/abs/ic700772a.html
*2)Mayer E, Inorg. chem, vol 12, 1973, Pg 1954-1952 {{doi-inline|doi:10.1021/ic50126a060|reference}}
*3)Thorne L R , Chem Phys Lett, vol 78, 1981, pg157-160 {{doi-inline|doi:10.1016/0009-2614(81)85575-3|reference}}
*4)Parry R W, J.am.chem.soc, vol 77, 1955, pg 2072-2074
*5)Adams R M, Inorg. Chem, vol 10, 1971, pg 2072-2074
*6) W T Klooster, J.Am.Chem.Soc., vol 121, 1999, pg 6337 {{doi-inline|doi:10.10121/ja9825332|reference}}
*7) Tubyanskaya V.S, Zh.fiz.khim, vol 40, 1966, pg 122-124
*8) Lloyd D.R, J.chem.soc.D, 1970, pg 1545-1546
*9) Crabtree Robert H, J.am.chem.soc, vol 121, 1999, 6333-6343
*10) http://biopact.com/2007/08/storing-hydrogen-in-solid-ammonia.html
*11) http://www.americanscientist.org/template/AssetDetail/assetid/45942

It07:h3nbh3

2007-10-23T14:04:21Z

Bbwt05: /* Uses and applications */

==Ammonia-borane==

Ammonia-borane has the following structure:

[[Image:screen_cap_ammonia_borane_2.jpg]] Point group = C3V

Right click on molecule to explore.
SMILES: [H][N@@]([H])([H])[B@]([H])([H])[H]

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>correct_conformation.ent
HEADER CSD ENTRY FUYVUQ01
CRYST1 5.4210 4.9450 5.0230 90.00 90.00 90.00 Pmn21
SCALE1 0.184468 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.202224 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.199084 0.000000
HETATM 1 B1 UNK 1 -0.000 -0.946 0.000 1.00 0.00 B
HETATM 2 H1 UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 3 H2 UNK 1 0.000 0.237 0.141 1.00 0.00 H
HETATM 4 N1 UNK 1 -0.000 -1.172 -1.585 1.00 0.00 N
HETATM 5 H3 UNK 1 -0.000 -1.879 -1.793 1.00 0.00 H
HETATM 6 H4 UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
HETATM 7 H1B UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 8 H4B UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 9 H1 UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 10 H4 UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 11 H1B UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 12 H4B UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 1 9 11
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 4 10 12
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 1
CONECT 10 4
CONECT 11 1
CONECT 12 4
MASTER 0 0 0 0 0 0 0 0 3 12 0 14 0
END
</inlineContents>
</jmolApplet>
</jmol>

== Crystal Structure ==
6

3D representation of the crystal unit cell. Right click on image to explore unit cell.

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>FUYVUQ02correct.ent
HEADER CSD ENTRY FUYVUQ02
CRYST1 5.3950 4.8870 4.9860 90.00 90.00 90.00 Pmn21
SCALE1 0.185357 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.204625 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.200562 0.000000
HETATM 1 N1 UNK 1 -0.000 1.148 1.566 1.00 0.00 N
HETATM 2 H1 UNK 1 -0.000 2.214 1.700 1.00 0.00 H
HETATM 3 H2 UNK 1 0.755 0.723 1.979 1.00 0.00 H
HETATM 4 B1 UNK 1 0.000 0.904 0.000 1.00 0.00 B
HETATM 5 H3 UNK 1 -0.000 -0.210 -0.299 1.00 0.00 H
HETATM 6 H4 UNK 1 0.998 1.290 -0.499 1.00 0.00 H
HETATM 7 H2 UNK 1 -0.755 0.723 1.979 1.00 0.00 H
HETATM 8 H4 UNK 1 -0.998 1.290 -0.499 1.00 0.00 H
HETATM 9 N1 UNK 1 5.395 1.148 1.566 1.00 0.00 N
HETATM 10 H1 UNK 1 5.395 2.214 1.700 1.00 0.00 H
HETATM 11 H2 UNK 1 6.150 0.723 1.979 1.00 0.00 H
HETATM 12 B1 UNK 1 5.395 0.904 0.000 1.00 0.00 B
HETATM 13 H3 UNK 1 5.395 -0.210 -0.299 1.00 0.00 H
HETATM 14 H4 UNK 1 6.393 1.290 -0.499 1.00 0.00 H
HETATM 15 H2 UNK 1 4.640 0.723 1.979 1.00 0.00 H
HETATM 16 H4 UNK 1 4.397 1.290 -0.499 1.00 0.00 H
HETATM 17 N1 UNK 1 2.698 3.739 4.059 1.00 0.00 N
HETATM 18 H1 UNK 1 2.698 2.673 4.193 1.00 0.00 H
HETATM 19 H2 UNK 1 1.943 4.164 4.472 1.00 0.00 H
HETATM 20 B1 UNK 1 2.698 3.983 2.493 1.00 0.00 B
HETATM 21 H3 UNK 1 2.698 5.097 2.194 1.00 0.00 H
HETATM 22 H4 UNK 1 1.700 3.597 1.994 1.00 0.00 H
HETATM 23 H2 UNK 1 3.453 4.164 4.472 1.00 0.00 H
HETATM 24 H4 UNK 1 3.695 3.597 1.994 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 10 11 12 15
CONECT 10 9
CONECT 11 9
CONECT 12 9 13 14 16
CONECT 13 12
CONECT 14 12
CONECT 15 9
CONECT 16 12
CONECT 17 18 19 20 23
CONECT 18 17
CONECT 19 17
CONECT 20 17 21 22 24
CONECT 21 20
CONECT 22 20
CONECT 23 17
CONECT 24 20
MASTER 0 0 0 0 0 0 0 0 3 24 0 24 0
END

</inlineContents>
</jmolApplet>
</jmol>

All cell parameter values in Å.
Method used to determine unit cell details is neutron diffraction
[[Image:screen_cap_crystal_cell.jpg]]

==Synthesis==

High purity (98%) and high yields (>95%) of ammonia borane can be achieved with reactions involving the direct addition of ammonium salts and sodium borohydride. 1

Ammonia borane can be synthesised by direct reaction of BH3(THF) and ammonia:
BH3(THF) + NH3 --> BH3NH3
The main product in this reaction is ammonia-borane.

===Other synthetic routes===

* Diborane + bisamminedihydroboriumtetrahydroborate --> ammonia-borane 2

Solvent: diglyme, Note: Slow reaction

*Ammodiumamidosulfonat + natrium boron hydride --> ammonia borane + H2 + NaNH2SO3 3

Solvent: liquid ammonia + ether, Purification/Isolation: solution was allowed to warm to room temperature; filtered; ether evaporated.

* Ammonium Chloride + Lithium Borohydride ---> ammonia borane + H2 4

Byproduct: LiCl

* Borane methylsulfide + ammonia --> ammonia borane + bisamminedihydroboriumtetrahydroborate 5

Solvent: No solvent required , General conditions: -20oC , Purification/Isolation: Recrystallisation from ether

==Uses and applications==

Ammonia borane is becoming an increasingly interesting molecule for hydrogen storage. It has found uses in applications such as motor vehicles and power generators in portable devices. Ammonia borane can hold large quantities of hydrogen but is not easily reversible. Part of the reason for this irreversibility is due to entropic reasons. When ammonia boarane is heated it decomposes into hydrogen gas and a few other compounds depending on conditions; as a result hydrogen can be readily evolved but the process cannot be easily reversed to recycle any unused hydrogen for later usage. Approximately one millilitre of ammonia borane can produce up to 1.8 litres of hydrogen gas. 10

Another advantage of using ammonia borane as hydrogen storage as opposed to hydrogen gas is because it has a melting point at -34 degrees Celsius, which is a lot higher than that of hydrogen. Also, ammonia borane becomes liquid at room temperature at 9 atmospheres pressure, this makes it much more convenient to use as a transportation fuel.11

Ammonia borane has also found many uses in organic synthesis, replacing diborane due to it being stable in air.

==Properties of Ammonia-borane==

===Bond Lengths===

*B-N: 1.58 Å
*B-H: 1.15 Å
*N-H: 0.96 Å

===Physical Properties===

*Appearance: Colourless, waxy solid
*Melting point: 104oC
*Boiling point: Decomposes
*Solubility in water: Good
*Decomposition: 80oC 7
*Ionization potential (Photoelectron spectroscopy [vertical]): 10.33eV-10.9eV 8

Ammonia-borane dissolves well in water due to the strong ionic component in the N-B bond given that there is a significant difference in the pauling electronegativity ( 3.04[N]-2.04[B]=1) between nitrogen and boron. This means that water molecules can easily solvate ammonia-borane as there is a strong attractive component between the permanent dipoles on the water molecules and the B-N bond in ammonia-borane.

*Density: 0.780 g/cm3
*Crystal structure: 14mm (tetragonal, >200K)
*Dipole moment: 5.2D 9

The dipole moment of ammonia borane arises due to the large difference in pauling electronegativity (as discussed with the solubility in water). Water has a dipole moment of 1.85D; therefore ammonia borane's dipole moment is approximately 3 times as much. To compare, this explains why water is a liquid in room temperature and pressure while ammonia borane is a solid due to the strong dipole-dipole interactions.

===Stability===

Ammonia borane is stable at room temperature and can last for hours when placed in aqueous solution. However, it decomposes rapidly when the compound is added to liquid ammonia or ether after addition of water. The molecule is also stable in anhydrous ether or liquid ammonia.

==Hazards==
*Flammable / keep away from heat
*Explosive (Heating causes ammonia borane to decompose into hydrogen gas!)

==References==

*1)http://pubs.acs.org/cgi-bin/abstract.cgi/inocaj/2007/46/i19/abs/ic700772a.html
*2)Mayer E, Inorg. chem, vol 12, 1973, Pg 1954-1952 {{doi-inline|doi:10.1021/ic50126a060|reference}}
*3)Thorne L R , Chem Phys Lett, vol 78, 1981, pg157-160 {{doi-inline|doi:10.1016/0009-2614(81)85575-3|reference}}
*4)Parry R W, J.am.chem.soc, vol 77, 1955, pg 2072-2074
*5)Adams R M, Inorg. Chem, vol 10, 1971, pg 2072-2074
*6) W T Klooster, J.Am.Chem.Soc., vol 121, 1999, pg 6337 {{doi-inline|doi:10.10121/ja9825332|reference}}
*7) Tubyanskaya V.S, Zh.fiz.khim, vol 40, 1966, pg 122-124
*8) Lloyd D.R, J.chem.soc.D, 1970, pg 1545-1546
*9) Crabtree Robert H, J.am.chem.soc, vol 121, 1999, 6333-6343
*10) http://biopact.com/2007/08/storing-hydrogen-in-solid-ammonia.html

It07:h3nbh3

2007-10-23T14:01:29Z

Bbwt05: /* Uses and applications */

==Ammonia-borane==

Ammonia-borane has the following structure:

[[Image:screen_cap_ammonia_borane_2.jpg]] Point group = C3V

Right click on molecule to explore.
SMILES: [H][N@@]([H])([H])[B@]([H])([H])[H]

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>correct_conformation.ent
HEADER CSD ENTRY FUYVUQ01
CRYST1 5.4210 4.9450 5.0230 90.00 90.00 90.00 Pmn21
SCALE1 0.184468 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.202224 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.199084 0.000000
HETATM 1 B1 UNK 1 -0.000 -0.946 0.000 1.00 0.00 B
HETATM 2 H1 UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 3 H2 UNK 1 0.000 0.237 0.141 1.00 0.00 H
HETATM 4 N1 UNK 1 -0.000 -1.172 -1.585 1.00 0.00 N
HETATM 5 H3 UNK 1 -0.000 -1.879 -1.793 1.00 0.00 H
HETATM 6 H4 UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
HETATM 7 H1B UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 8 H4B UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 9 H1 UNK 1 0.867 -1.385 0.407 1.00 0.00 H
HETATM 10 H4 UNK 1 -0.683 -0.806 -1.894 1.00 0.00 H
HETATM 11 H1B UNK 1 -0.867 -1.385 0.407 1.00 0.00 H
HETATM 12 H4B UNK 1 0.683 -0.806 -1.894 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 1 9 11
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 4 10 12
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 1
CONECT 10 4
CONECT 11 1
CONECT 12 4
MASTER 0 0 0 0 0 0 0 0 3 12 0 14 0
END
</inlineContents>
</jmolApplet>
</jmol>

== Crystal Structure ==
6

3D representation of the crystal unit cell. Right click on image to explore unit cell.

<jmol>
<jmolApplet>
<size>250</size>
<color>black</color>
<script>zoom 80; cpk -25;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>FUYVUQ02correct.ent
HEADER CSD ENTRY FUYVUQ02
CRYST1 5.3950 4.8870 4.9860 90.00 90.00 90.00 Pmn21
SCALE1 0.185357 -0.000000 -0.000000 0.000000
SCALE2 0.000000 0.204625 -0.000000 0.000000
SCALE3 0.000000 0.000000 0.200562 0.000000
HETATM 1 N1 UNK 1 -0.000 1.148 1.566 1.00 0.00 N
HETATM 2 H1 UNK 1 -0.000 2.214 1.700 1.00 0.00 H
HETATM 3 H2 UNK 1 0.755 0.723 1.979 1.00 0.00 H
HETATM 4 B1 UNK 1 0.000 0.904 0.000 1.00 0.00 B
HETATM 5 H3 UNK 1 -0.000 -0.210 -0.299 1.00 0.00 H
HETATM 6 H4 UNK 1 0.998 1.290 -0.499 1.00 0.00 H
HETATM 7 H2 UNK 1 -0.755 0.723 1.979 1.00 0.00 H
HETATM 8 H4 UNK 1 -0.998 1.290 -0.499 1.00 0.00 H
HETATM 9 N1 UNK 1 5.395 1.148 1.566 1.00 0.00 N
HETATM 10 H1 UNK 1 5.395 2.214 1.700 1.00 0.00 H
HETATM 11 H2 UNK 1 6.150 0.723 1.979 1.00 0.00 H
HETATM 12 B1 UNK 1 5.395 0.904 0.000 1.00 0.00 B
HETATM 13 H3 UNK 1 5.395 -0.210 -0.299 1.00 0.00 H
HETATM 14 H4 UNK 1 6.393 1.290 -0.499 1.00 0.00 H
HETATM 15 H2 UNK 1 4.640 0.723 1.979 1.00 0.00 H
HETATM 16 H4 UNK 1 4.397 1.290 -0.499 1.00 0.00 H
HETATM 17 N1 UNK 1 2.698 3.739 4.059 1.00 0.00 N
HETATM 18 H1 UNK 1 2.698 2.673 4.193 1.00 0.00 H
HETATM 19 H2 UNK 1 1.943 4.164 4.472 1.00 0.00 H
HETATM 20 B1 UNK 1 2.698 3.983 2.493 1.00 0.00 B
HETATM 21 H3 UNK 1 2.698 5.097 2.194 1.00 0.00 H
HETATM 22 H4 UNK 1 1.700 3.597 1.994 1.00 0.00 H
HETATM 23 H2 UNK 1 3.453 4.164 4.472 1.00 0.00 H
HETATM 24 H4 UNK 1 3.695 3.597 1.994 1.00 0.00 H
CONECT 1 2 3 4 7
CONECT 2 1
CONECT 3 1
CONECT 4 1 5 6 8
CONECT 5 4
CONECT 6 4
CONECT 7 1
CONECT 8 4
CONECT 9 10 11 12 15
CONECT 10 9
CONECT 11 9
CONECT 12 9 13 14 16
CONECT 13 12
CONECT 14 12
CONECT 15 9
CONECT 16 12
CONECT 17 18 19 20 23
CONECT 18 17
CONECT 19 17
CONECT 20 17 21 22 24
CONECT 21 20
CONECT 22 20
CONECT 23 17
CONECT 24 20
MASTER 0 0 0 0 0 0 0 0 3 24 0 24 0
END

</inlineContents>
</jmolApplet>
</jmol>

All cell parameter values in Å.
Method used to determine unit cell details is neutron diffraction
[[Image:screen_cap_crystal_cell.jpg]]

==Synthesis==

High purity (98%) and high yields (>95%) of ammonia borane can be achieved with reactions involving the direct addition of ammonium salts and sodium borohydride. 1

Ammonia borane can be synthesised by direct reaction of BH3(THF) and ammonia:
BH3(THF) + NH3 --> BH3NH3
The main product in this reaction is ammonia-borane.

===Other synthetic routes===

* Diborane + bisamminedihydroboriumtetrahydroborate --> ammonia-borane 2

Solvent: diglyme, Note: Slow reaction

*Ammodiumamidosulfonat + natrium boron hydride --> ammonia borane + H2 + NaNH2SO3 3

Solvent: liquid ammonia + ether, Purification/Isolation: solution was allowed to warm to room temperature; filtered; ether evaporated.

* Ammonium Chloride + Lithium Borohydride ---> ammonia borane + H2 4

Byproduct: LiCl

* Borane methylsulfide + ammonia --> ammonia borane + bisamminedihydroboriumtetrahydroborate 5

Solvent: No solvent required , General conditions: -20oC , Purification/Isolation: Recrystallisation from ether

==Uses and applications==

Ammonia borane is becoming an increasingly interesting molecule for hydrogen storage. It has found uses in applications such as motor vehicles and power generators in portable devices. Ammonia borane can hold large quantities of hydrogen but is not easily reversible. Part of the reason for this irreversibility is due to entropic reasons. When ammonia boarane is heated it decomposes into hydrogen gas and a few other compounds depending on conditions; as a result hydrogen can be readily evolved but the process cannot be easily reversed to recycle any unused hydrogen for later usage. Approximately one millilitre of ammonia borane can produce up to 1.8 litres of hydrogen gas.

Another advantage of using ammonia borane as hydrogen storage as opposed to hydrogen gas is because it has a melting point at -34 degrees Celsius, which is a lot higher than that of hydrogen.
10 Ammonia borane has also found many uses in organic synthesis, replacing diborane due to it being stable in air.

==Properties of Ammonia-borane==

===Bond Lengths===

*B-N: 1.58 Å
*B-H: 1.15 Å
*N-H: 0.96 Å

===Physical Properties===

*Appearance: Colourless, waxy solid
*Melting point: 104oC
*Boiling point: Decomposes
*Solubility in water: Good
*Decomposition: 80oC 7
*Ionization potential (Photoelectron spectroscopy [vertical]): 10.33eV-10.9eV 8

Ammonia-borane dissolves well in water due to the strong ionic component in the N-B bond given that there is a significant difference in the pauling electronegativity ( 3.04[N]-2.04[B]=1) between nitrogen and boron. This means that water molecules can easily solvate ammonia-borane as there is a strong attractive component between the permanent dipoles on the water molecules and the B-N bond in ammonia-borane.

*Density: 0.780 g/cm3
*Crystal structure: 14mm (tetragonal, >200K)
*Dipole moment: 5.2D 9

The dipole moment of ammonia borane arises due to the large difference in pauling electronegativity (as discussed with the solubility in water). Water has a dipole moment of 1.85D; therefore ammonia borane's dipole moment is approximately 3 times as much. To compare, this explains why water is a liquid in room temperature and pressure while ammonia borane is a solid due to the strong dipole-dipole interactions.

===Stability===

Ammonia borane is stable at room temperature and can last for hours when placed in aqueous solution. However, it decomposes rapidly when the compound is added to liquid ammonia or ether after addition of water. The molecule is also stable in anhydrous ether or liquid ammonia.

==Hazards==
*Flammable / keep away from heat
*Explosive (Heating causes ammonia borane to decompose into hydrogen gas!)

==References==

*1)http://pubs.acs.org/cgi-bin/abstract.cgi/inocaj/2007/46/i19/abs/ic700772a.html
*2)Mayer E, Inorg. chem, vol 12, 1973, Pg 1954-1952 {{doi-inline|doi:10.1021/ic50126a060|reference}}
*3)Thorne L R , Chem Phys Lett, vol 78, 1981, pg157-160 {{doi-inline|doi:10.1016/0009-2614(81)85575-3|reference}}
*4)Parry R W, J.am.chem.soc, vol 77, 1955, pg 2072-2074
*5)Adams R M, Inorg. Chem, vol 10, 1971, pg 2072-2074
*6) W T Klooster, J.Am.Chem.Soc., vol 121, 1999, pg 6337 {{doi-inline|doi:10.10121/ja9825332|reference}}
*7) Tubyanskaya V.S, Zh.fiz.khim, vol 40, 1966, pg 122-124
*8) Lloyd D.R, J.chem.soc.D, 1970, pg 1545-1546
*9) Crabtree Robert H, J.am.chem.soc, vol 121, 1999, 6333-6343
*10) http://biopact.com/2007/08/storing-hydrogen-in-solid-ammonia.html