View source for Cytisine


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<td valign="top" width="50%"><strong>Other Names</strong>

Baptitoxin, CYtiton, laburnin, 1,2,3,4,5,6-hexahydro8H-

1,5-methano-pyrido[1,2a] [1,5]diazocin-8-ol,

sophorin, ulexin

Substance type: quinolizidine alkaloid, lupine

alkaloid

Cytisine is found in numerous legumes (Leguminosae)

(Plugge 1895), such as the rain shower

tree (Laburnum anagyroides Medikus [syn. Cytisus

laburnum 1.] ).497

Since cytisine acts to stimulate the central

nervous system, states of excitation and

confusion (with hallucinations, delirium),

muscle spasms, as well as general clonic-tonic

spasms in the extremities not infrequently

occur. (Roth et al. 1994,443*)

Cytisine docks to the acetylcholine (ACh)

receptors of the central nervous system, the

ganglia, and the neuromuscular endplate. The

ganglia-blocking effects of cytisine are similar to

those of nicotine and can induce strychninelike

spasms, especially hallucinations, and even

unconsciousness and ultimately death. However,

the lethal dosage for humans is unknown (Roth et

al. 1994, 801 f. *). The nicotine-like effects also

explain the ethnopharmacological use of plants

containing cytisine as tobacco substitutes.

Other lupine alkaloids and cytisine derivatives

have been found in many plants from the Family

Leguminosae, including Lupinus spp. and Echinosophora

koreensis Nakai (a close relative of the

genus Sophora) (Murakoshi et al. 1977).

<strong>Plants Containing Cytisine</strong>

(from Bock 1994,75 ff.*; Rompp 1995*; Roth et al. 1994*; supplemented)
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<td valign="top" width="319"><strong>Stock </strong><strong>Plant</strong></td>
<td valign="top" width="319"><strong>Distribution</strong></td>
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<td valign="top" width="319"><em>Ammodendron </em>spp.</td>
<td valign="top" width="319">&nbsp;</td>
</tr>
<tr>
<td valign="top" width="319"><em>Anagyris </em>spp.</td>
<td valign="top" width="319">southern Europe</td>
</tr>
<tr>
<td valign="top" width="319"><em>Baptisia </em>spp.</td>
<td valign="top" width="319">North America</td>
</tr>
<tr>
<td valign="top" width="319"><em>Colutea.arborescens </em>1.</td>
<td valign="top" width="319">Mediterranean region</td>
</tr>
<tr>
<td valign="top" width="319"><em>Calutea </em>spp.</td>
<td valign="top" width="319">southeastern Europe, Asia Minor</td>
</tr>
<tr>
<td valign="top" width="319"><em>Cytisus canariensis</em></td>
<td valign="top" width="319">Canary Islands, Mexico</td>
</tr>
<tr>
<td valign="top" width="319"><em>Cytisus </em>spp.</td>
<td valign="top" width="319">Europe</td>
</tr>
<tr>
<td valign="top" width="319"><em>Eucresta </em>spp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Genista germanica </em>1.</td>
<td valign="top" width="319">central Europe</td>
</tr>
<tr>
<td valign="top" width="319"><em>Genista tinctoria </em>1.</td>
<td valign="top" width="319">Europe</td>
</tr>
<tr>
<td valign="top" width="319"><em>Labttrnum alpinum </em>(Mill.) Bercht.et Presl</td>
<td valign="top" width="319">Alps, southern Europe</td>
</tr>
<tr>
<td valign="top" width="319">[syn. <em>Cytisus alpinusMill.]</em></td>
<td valign="top" width="319">&nbsp;</td>
</tr>
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<td valign="top" width="319"><em>Laburnum anagyroides </em>Medik. [syn. <em>Laburnum vulgare</em></td>
<td valign="top" width="319">central and southern Europe</td>
</tr>
<tr>
<td valign="top" width="319">Bercht.et Pres!' <em>Cytisus laburnum </em>1.]</td>
<td valign="top" width="319">&nbsp;</td>
</tr>
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<td valign="top" width="319"><em>Lamprolobium fruticosumBenth.</em></td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Lampralobium grandiflorum </em>Everist</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Hovea acutifalia </em>Cunn.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Hoveaspp.</em></td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Plagiocarpus axiUaris </em>Benth.</td>
<td valign="top" width="319">Australia</td>
</tr>
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<td valign="top" width="319"><em>Sophora secundiflora</em></td>
<td valign="top" width="319">Mexico, Texas</td>
</tr>
<tr>
<td valign="top" width="319"><em>Sophora tomentosa </em>1.</td>
<td valign="top" width="319">Australia, Oceania</td>
</tr>
<tr>
<td valign="top" width="319"><em>Spartium junceum </em>1.</td>
<td valign="top" width="319">Spain, southern Europe</td>
</tr>
<tr>
<td valign="top" width="319"><em>Strongylodon macrobotrys </em>A.Gray</td>
<td valign="top" width="319">Philippines</td>
</tr>
<tr>
<td valign="top" width="319"><em>Templetonia </em>spp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Thel'mopsis </em>spp.</td>
<td valign="top" width="319">Australia</td>
</tr>
<tr>
<td valign="top" width="319"><em>Ulex europaeus </em>1.</td>
<td valign="top" width="319">central Europe</td>
</tr>

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&nbsp;</td>
<td valign="top" width="53%"><strong>Commercial Forms and Regulations

</strong>Cytisine is sold in its pure form and is not subject

to any regulations (Roth et al. 1994, 802).<strong></strong>

Literature

See also the entries for Cytisus spp. and Sophora

secundiflora.

Hayman, Alison R., and David O. Gray. 1989.

Hydroxynorcytisine, a quinolizidine alkaloid

from Laburnum anagyroides. Phytochemistry 28

(2): 673-75.

Murakoshi, Isamu, Kyoko Fukuchi, Joju Haginiwa,

Shigeru Ohmiya, and Hirotaka Otomasu. 1977.

N-(3-oxobutyl)cytisine: A new lupin alkaloid from Echinosophora koreensis. Phytochemistry

16:1460-6l.

Plugge, P. C. 1895. Uber das Vorkommen von Cytisin

in verschiedenen Papilionaceae. Archiv fur

Pharmazie 233:430 ff.

Plugge, P. C., and A. Rauwerda. 1896. Fortgesetzte

Untersuchungen Dber das Vorkommen von

Cytisin in verschiedenen Papilionaceae. Archiv

fur Pharmazie 234:685 ff.

Seeger, R., and H. G. Neumann. 1992. Cytisin.

Deutsche Apotheker Zeitung 132:303-6.</td>
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[[Category:Chemicals]]