Tropine

Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol.[1]

Tropine

Names
IUPAC name (3-endo)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Other names α-Tropine; Tropanol
Identifiers
CAS Number	120-29-6
3D model (JSmol)	Interactive image
ChemSpider	10180559
ECHA InfoCard	100.003.986
MeSH	Tropine
PubChem CID	8424
UNII	7YXR19M72Y
CompTox Dashboard (EPA)	DTXSID2049399
InChI InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3/t6-,7+,8+ Key: CYHOMWAPJJPNMW-JIGDXULJSA-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
SMILES CN1[C@@H]2CC[C@H]1C[C@H](C2)O
Properties
Chemical formula	C8H15NO
Molar mass	141.214 g·mol^−1
Appearance	Hygroscopic plates
Density	1.016 g/cm^3 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[1]
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 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.[2]

Chemistry

Synthesis

It can be prepared by hydrolysis of atropine[3]

See also

• Pseudotropine
• Atropine
• Tropinone
• Tropane alkaloid

References

1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–564, ISBN 0-8493-0594-2
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.
3. "Cocaine analog in two steps from native plant material".