Tropine

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Tropine
Names
Preferred IUPAC name
(1R,3r,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Other names
α-Tropine; Tropanol; 3-Tropanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.986 Edit this at Wikidata
MeSH Tropine
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 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
 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 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

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][7]

In the laboratory it is made by the reduction of tropinone:[8] Patent:[9][10]

Derivatives

List of derivatives that can be made from tropine:

  1. AHN 1-055 HCl: [202646-03-5][11][12] Patent:[13] Selfsame as JHW-007 (N-butyl group). This benzhydrol aromatic entity is the same as for flunamine & vanoxerine.
  2. Atropine[14]
  3. Atromepine[15][16]
  4. Benztropine[17][18]
  5. Bemesetron[19][20]
  6. Butropium bromide (Coliopan®)[21][22]
  7. Ciclotropium (wrong stereochemistry if employing this method)[23]
  8. Clobenztropine[24][25][26][27]
  9. D-13264[28] (atropine quat).
  10. Decitropine [1242-69-9][29]
  11. Deptropine[30][31]
  12. Fentonium[32][33]
  13. Flutropium bromide (wrong stereoisomer using this method of synthesis).[34]
  14. Homatropine[35]
  15. PG-9 [156143-26-9] Maleate salt: [155649-00-6] Synthesis:[36][37] Pharmacol:[38][39][40]
  16. Methoxytropacin HCl: [74051-44-8]
  17. Prampine [7009-65-6][citation needed]
  18. Pudafensine[41] (by Mitsunobu inversion chemistry)
  19. SM-21 (other codenames covered too)[37][42]
  20. SM-25 is the ester between tropine and clofibric acid.[42]
  21. Tropabazate[citation needed]
  22. Tropacine[43][44][45]
  23. Tropacocaine (by Mitsunobu inversion chemistry)[6]
  24. Tropanserin[46][47]
  25. Tropatepine[48]
  26. Tropine benzilate ("BAT")
  27. Tropirine[49][50]
  28. Tropodifene[51]
  29. Xenytropium[52]
  30. Zepastine[53]
  31. 3-Perfluorophenoxytropane (PC14575207)[54]
  32. PC46905316 (Ibuprofen)[36] &PC16115711 (Naproxen).[citation needed]
  33. Tropine p-chlorophenoxyacetate [6658-61-3][55] (c.f. Meclofenoxate).

See also

References

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