Pseudotropine

Pseudotropine
Clinical data
Other names	3β-Tropanol; 1αH,5αH-Tropan-3β-ol
Identifiers
	IUPAC name (1R,3R,5S)-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol;
CAS Number	135-97-7;
PubChem CID	449293;
UNII	L9Q7Z9D09L;
ChEBI	CHEBI:15742;
ChEMBL	ChEMBL1235490;
CompTox Dashboard (EPA)	DTXSID501026533 ;
ECHA InfoCard	100.004.751
Chemical and physical data
Formula	C8H15NO
Molar mass	141.214 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1[C@@H]2CC[C@H]1C[C@@H](C2)O;
	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-RNLVFQAGSA-N;

Pseudotropine (3β-tropanol, ψ-tropine, 3-pseudotropanol, or PTO) is a derivative of tropane and an isomer of tropine. Pseudotropine can be found in the Coca plant along with several other alkaloids ^[1]

Synthesis

In the laboratory it is made by the reduction of tropinone:^[2] According to the article, a good stereoselectivity of pseudotropine over endotropine could be achieved when employing a Meerwein–Ponndorf–Verley reduction or sodium metal in n-pentanol.

Derivatives

Pudafensine
Tropigline (Tigloidine, ticloidine) [533-08-4] (E)-form Produced by Physalis peruviana. Anticholinergic, anti parkinsonian drug.^[3]^[4]^[5]
Convolamine
Valtropine
Pseudotropine benzoate (tropacocaine)

References

^ Biondich AS, Joslin JD (2016). "Coca: The History and Medical Significance of an Ancient Andean Tradition". Emergency Medicine International. 2016 4048764. doi:10.1155/2016/4048764. PMC 4838786. PMID 27144028.
^ Beckett, A. H., Harper, N. J., Balon, A. D. J., Watts, T. H. E. (January 1959). "Stereochemistry of the reduction of tropinone". Tetrahedron. 6 (4): 319–330. doi:10.1016/0040-4020(59)80012-0.
^ Beresford, P. J., Woolley, J. G. (October 1974). "Biosynthesis of ticloidine in Physalis peruviana". Phytochemistry. 13 (10): 2143–2144. doi:10.1016/0031-9422(74)85016-8.
^ Barger, G., Martin, Wm. F., Mitchell, Wm. (1937). "383. The minor alkaloids of Duboisia myoporoides". Journal of the Chemical Society (Resumed): 1820. doi:10.1039/jr9370001820.
^ Rabot, S. (May 1995). "Tigloyl-CoA:pseudotropine acyl transferase—An enzyme of tropane alkaloid biosynthesis". Phytochemistry. 39 (2): 315–322. doi:10.1016/0031-9422(94)00907-B.

[1] Biondich AS, Joslin JD (2016). "Coca: The History and Medical Significance of an Ancient Andean Tradition". Emergency Medicine International. 2016 4048764. doi:10.1155/2016/4048764. PMC 4838786. PMID 27144028.

[2] Beckett, A. H., Harper, N. J., Balon, A. D. J., Watts, T. H. E. (January 1959). "Stereochemistry of the reduction of tropinone". Tetrahedron. 6 (4): 319–330. doi:10.1016/0040-4020(59)80012-0.

[3] Beresford, P. J., Woolley, J. G. (October 1974). "Biosynthesis of ticloidine in Physalis peruviana". Phytochemistry. 13 (10): 2143–2144. doi:10.1016/0031-9422(74)85016-8.

[4] Barger, G., Martin, Wm. F., Mitchell, Wm. (1937). "383. The minor alkaloids of Duboisia myoporoides". Journal of the Chemical Society (Resumed): 1820. doi:10.1039/jr9370001820.

[5] Rabot, S. (May 1995). "Tigloyl-CoA:pseudotropine acyl transferase—An enzyme of tropane alkaloid biosynthesis". Phytochemistry. 39 (2): 315–322. doi:10.1016/0031-9422(94)00907-B.

[1]

[2]

[3]

[4]

[5]

Synthesis

Derivatives

See also

References