Tropine

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
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:
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).
N verify (what is YN ?)
Infobox references

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]

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]
  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
  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).
  33. Tropine p-chlorophenoxyacetate [6658-61-3][55] (c.f. Meclofenoxate).

See also

References

  1. ^ a b c "8-Methyl-8-azabicyclo[3.2.1]octan-3-ol".
  2. ^ a b c d "Safety Data Sheet - Tropine". www.sigmaaldrich.com.
  3. ^ a b c d "Medical Definition of TROPINE".
  4. ^ 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
  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. ^ a b "[2008-09-10] Cocaine analog in two steps from native plant material". www.seanmichaelragan.com.
  7. ^ Ladenburg, A (January 1902). "Bildung von Tropin aus Tropidin und die Synthese des Atropins". Berichte der deutschen chemischen Gesellschaft. 35 (1): 1159–1162. doi:10.1002/cber.190203501191.
  8. ^ Beckett, AH, Harper, NJ, Balon, ADJ, Watts, THE (January 1959). "Stereochemistry of the reduction of tropinone". Tetrahedron. 6 (4): 319–330. doi:10.1016/0040-4020(59)80012-0.
  9. ^ Rolf Sachse & Albert Schaupp, U.S. patent 6,005,110 (1999 to Pfleger R Chemische Fabrik GmbH).
  10. ^ Van de Kamp, Sletzinger, U.S. patent 2,366,760 (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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  14. ^ Al-Badr, A. A., Muhtadi, F. J. (1985). "Analytical Profiles of Drug Substances". Atropine. Vol. 14. Elsevier. pp. 325–389. doi:10.1016/S0099-5428(08)60585-7.
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  35. ^ Chemnitius, F. (1927). "Zur Darstellung des Homatropins". Journal für Praktische Chemie. 17 (1): 142–146. ISSN 0021-8383. doi:10.1002/prac.19271170105.
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