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Tropine

From Wikipedia, the free encyclopedia
Tropine
Names
Preferred IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Other names
α-Tropine; Tropanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.003.986Edit this at Wikidata
MeSHTropine
UNII
  • InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ ☒N
    Key: CYHOMWAPJJPNMW-JIGDXULJSA-N ☒N
  • InChI=1/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+
    Key: CYHOMWAPJJPNMW-JIGDXULJBD
  • CN1[C@@H]2CC[C@H]1C[C@H](C2)O
Properties
C8H15NO
Molar mass141.214 g·mol−1
AppearanceWhitehygroscopic crystalline powder[1][2][3] or plates
OdorAmine-like[2]
Density1.045 g/cm3 at 25 °C[2]
1.016 g/cm3 at 100 °C
Melting point64 °C (147 °F; 337 K)
Boiling point233 °C (451 °F; 506 K)
SolubilityVery soluble in water,diethyl ether,ethanol[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
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):
  • >2000 mg/kg (rat, oral)[2]
  • 139 mg/kg (mouse, intraperitoneal)
  • >50 mg/kg (rabbit, intravenous)
  • 280 mg/kg (mouse, intraperitoneal)
  • >50 mg/kg (rabbit, intravenous)[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Tropine is a derivative oftropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol.[4] It is a poisonous whitehygroscopic crystalline powder.[3] It is aheterocyclicalcohol and anamine.[3]

Tropine is acentral building block of many chemicals active in the nervous system, includingtropane alkaloids. Some of these compounds, such aslong-acting muscarinic antagonists are used as medicines because of these effects.[5]

Occurrence

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Tropine is a natural product found in the plants of deadly nightshade (Atropa belladonna) and devil's trumpet (Datura stramonium).[1]

Chemistry

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Synthesis

[edit]

It can be prepared by hydrolysis ofatropine[6] or othersolanaceousalkaloids.[3]

See also

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References

[edit]
  1. ^abc"8-Methyl-8-azabicyclo[3.2.1]octan-3-ol".
  2. ^abcd"Safety Data Sheet - Tropine".www.sigmaaldrich.com.
  3. ^abcd"Medical Definition of TROPINE".
  4. ^abLide, David R. (1998),Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–564,ISBN 0-8493-0594-2
  5. ^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.
  6. ^"[2008-09-10] Cocaine analog in two steps from native plant material".www.seanmichaelragan.com.
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