Chemistry:Tropine
From HandWiki
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| Names | |||
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| Preferred IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol | |||
| Other names
α-Tropine; Tropanol
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| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| MeSH | Tropine | ||
PubChem CID
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| Properties | |||
| C8H15NO | |||
| Molar mass | 141.214 g·mol−1 | ||
| Appearance | White hygroscopic crystalline powder[1][2][3] or plates | ||
| Odor | Amine-like[2] | ||
| Density | 1.045 g/cm3 at 25 °C[2] 1.016 g/cm3 at 100 °C | ||
| Melting point | 64 °C (147 °F; 337 K) | ||
| Boiling point | 233 °C (451 °F; 506 K) | ||
| Hazards | |||
| Main hazards | Toxic | ||
| GHS pictograms |  
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| GHS Signal word | Danger | ||
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| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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| Infobox references | |||
Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol.[4] It is a poisonous white hygroscopic crystalline powder.[3] It is a heterocyclic alcohol and an amine.[3]
Tropine is a central building block of many chemicals active in the nervous system, including tropane alkaloids. Some of these compounds, such as long-acting muscarinic antagonists are used as medicines because of these effects.[5]
Occurrence
Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).[1]
Chemistry
Synthesis
It can be prepared by hydrolysis of atropine[6] or other solanaceous alkaloids.[3]
See also
- Pseudotropine
- Atropine
- Tropinone
- Tropane alkaloid
References
- ↑ 1.0 1.1 1.2 https://pubchem.ncbi.nlm.nih.gov/compound/8424
- ↑ 2.0 2.1 2.2 2.3 https://www.sigmaaldrich.com/GB/en/sds/aldrich/93550
- ↑ 3.0 3.1 3.2 3.3 https://www.merriam-webster.com/medical/tropine
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs namedhand - ↑ Ping, Yu; Li, Xiaodong; You, Wenjing; Li, Guoqiang; Yang, Mengquan; Wei, Wenping; Zhou, Zhihua; Xiao, Youli (10 June 2019). "Production of the Plant-Derived Tropine and Pseudotropine in Yeast". ACS Synthetic Biology 8 (6): 1257–1262. doi:10.1021/acssynbio.9b00152. PMID 31181154.
- ↑ [2008-09-10_Cocaine_analog_in_two_steps_from_native_plant_material.shtml "Cocaine analog in two steps from native plant material"]. https://www.seanmichaelragan.com/html/[2008-09-10]_Cocaine_analog_in_two_steps_from_native_plant_material.shtml.
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