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Tropine

1.016 g/cm3 at 100 °C

Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. It is a poisonous white hygroscopic crystalline powder. It is a heterocyclic alcohol and an amine.

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.

Occurrence

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

Chemistry

Synthesis

It can be prepared by hydrolysis of atropine or other solanaceous alkaloids.

In the laboratory it is made by the reduction of tropinone: Patent:

Derivatives

List of derivatives that can be made from tropine:

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

References

References

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  2. "Safety Data Sheet - Tropine".
  3. "Medical Definition of TROPINE".
  4. Lide, David R.. (1998). "Handbook of Chemistry and Physics". CRC Press.
  5. (10 June 2019). "Production of the Plant-Derived Tropine and Pseudotropine in Yeast". ACS Synthetic Biology.
  6. "[2008-09-10] Cocaine analog in two steps from native plant material".
  7. (January 1902). "Bildung von Tropin aus Tropidin und die Synthese des Atropins". Berichte der deutschen chemischen Gesellschaft.
  8. (January 1959). "Stereochemistry of the reduction of tropinone". Tetrahedron.
  9. Rolf Sachse & Albert Schaupp, {{US patent. 6005110 (1999 to Pfleger R Chemische Fabrik GmbH).
  10. Van de Kamp, Sletzinger, {{US patent. 2366760 (1945 to [[Merck & Co.]])
  11. Newman, Amy Hauck; Allen, Andrew C.; Izenwasser, Sari; Katz, Jonathan L. (1994). "Novel 3.alpha.-(Diphenylmethoxy)tropane Analogs: Potent Dopamine Uptake Inhibitors without Cocaine-like Behavioral Profiles". Journal of Medicinal Chemistry. 37 (15): 2258–2261. doi:10.1021/jm00041a002.
  12. Newman, Amy Hauck; Kline, Richard H.; Allen, Andrew C.; Izenwasser, Sari; George, Clifford; Katz, Jonathan L. (1995). "Novel 4'-Substituted and 4',4-Disubstituted 3.alpha.-(Diphenylmethoxy)tropane Analogs as Potent and Selective Dopamine Uptake Inhibitors". Journal of Medicinal Chemistry. 38 (20): 3933–3940. doi:10.1021/jm00020a006.
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  15. Melone, Gaetano; Vecchi, Alberto; Pagani, Giuseppe; Testa, Emilio (1960). "Notes- Tropine DL-α-Methyltropate (Methylatropine) and Its Optical Antipodes". The Journal of Organic Chemistry. 25 (5): 859–861. doi:10.1021/jo01075a624.
  16. Scarselli, Veniero; Cignarella, Giorgio; Maffii, Giulio (1964). "Structural Changes and Anticholinergic Activity in a Class of Tropic and α-Methyltropic Acid Derivatives". Journal of Medicinal Chemistry. 7 (2): 237–238. doi:10.1021/jm00332a026.
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  44. XU, Rong; SIM, Meng-Kwoon; GO, Mei-Lin (1998). "Synthesis, Antimuscarinic Activity and Quantitative Structure-Activity Relationship (QSAR) of Tropinyl and Piperidinyl Esters". CHEMICAL & PHARMACEUTICAL BULLETIN. 46 (2): 231–241. doi:10.1248/cpb.46.231.
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