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Sunday 23 November 2014

The Cocaine Diastereoisomers




Table 1.
Melting point data °C.
Compound
Findlay4
Sinnema
et al.
5
Willstätter
et al.
7
Merck9
This
Work
(-)-Cocaine
-
-
-
98
96-97
(+)-Cocaine
-
-
98
-
-
(±)-Cocaine
79-80
-
79-80
-
74-75
(-)-Cocaine HCl
-
-
192
195
194-196
(±)-Cocaine HCl
187
-
187
-
186-188
(+)-Pseudococaine
-
-
43-45
47
-
(±)-Pseudococaine
81.5
-
81.5
-
oil
(+)-Pseudococaine HCl
-
-
205
210
208-210
(±)-Pseudococaine HCl
205.5
-
205-206
-
202-204
(±)-Allococaine
93-95
95-97
-
-
94-96
(±)-Allococaine HCl
oil
oil
-
-
oil
(±)-Pseudoallococaine
82-84
83-84
-
-
oil
(±)-Pseudoallococaine HCl
201.5
209-210
-
-
203-205
\\\

Proton Nuclear Magnetic Resonance
1H-NMR Spectra
(in CDCl3)
Fig. 4.Cocaine
Fig. 5.Pseudococaine
Fig. 6.Allococaine
Fig. 7.Pseudoallococaine
Proton NMR spectra of the diastereoisomeric cocaines are significantly different. Major differences are seen in the chemical shifts associated with the respective C-3 protons. In addition, the coupling patterns that arise from the vicinal coupling of C-2 and C-4 protons with the C-3 proton are first order and relate nicely to the Karplus equation5.
That the diastereoisomeric cocaines, can easily be distinguished by observation of the chemical shifts and coupling patterns associated with the C-3 proton does not imply that other differences do not exist. In fact, virtually every proton in these molecules exhibits a different chemical shift or coupling pattern

COCAINE














  1. Findlay, S. P., J. Am. Chem. Soc., 76, 2855-2862 (1954)
  2. Findlay, S. P., J. Org. Chem., 21, 711 (1956)
  3. Findlay, S. P., J. Org. Chem., 22, 1385-1394 (1957)
  4. Findlay, S. P., J. Org. Chem., 24, 1540-1550 (1959)
  5. A. Sinnema, L Maat, AJ vd.Gugten, HC Beyerman, Rec. Trav. Chim. Pays-Bas 87, 1027-1041 (1968)
  6. Robinson, R., Journal of the Chemical Society (London), 111, 762-768 (1917)
  7. Willstätter, R., Wolfes, O., and Mäder, H., Justus Liebigs Annalen der Chemie, 434, 111-139 (1923)
  8. Fulton, C. C., Modern Microcrystal Tests for Drugs, Wiley, New York, 1969, pp. 21-24.
  9. The Merck Index, 9th ed., 1976, Merck and Co., Rahway, N.J.
  10. Fulton, C. C., Modern Microcrystal Test for Drugs, Wiley, New York, 1969, pp. 318-19.
  11. Clarke, E. G. C., Isolation and Identification of Drugs, Pharmaceutical Press, London, 1971, pp. 139-41.
  12. Fulton, C. G., Modern Microcrystal Tests for Drugs, Wiley, New York, 1969, p. 301.
  13. Cooper, D. A. and Allen, A. C., "A Mechanistic Interpretation of the Mass Spectrum of Cocaine",
    31st Annual Meeting of the American Academy of Forensic Sciences, Atlanta, Georgia, Feb. 1979.
  14. Eliel, E. L., Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962, pp. 43-47.




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