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]
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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 | |||
ECHA InfoCard | 100.003.986 | ||
MeSH | Tropine | ||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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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) | ||
Solubility | Very soluble in water, diethyl ether, ethanol[4] | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Toxic | ||
GHS labelling: | |||
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Danger | |||
H301, H302, H312, H332 | |||
P261, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P405, P501 | |||
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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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
editTropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).[1]
Chemistry
editSynthesis
editIt can be prepared by hydrolysis of atropine[6] or other solanaceous alkaloids.[3]
See also
editReferences
edit- ^ a b c "8-Methyl-8-azabicyclo[3.2.1]octan-3-ol".
- ^ a b c d https://www.sigmaaldrich.com/GB/en/sds/aldrich/93550 [bare URL]
- ^ a b c d "Medical Definition of TROPINE".
- ^ a b Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–564, ISBN 0-8493-0594-2
- ^ 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. S2CID 184484993.
- ^ "Cocaine analog in two steps from native plant material".