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An ab initio SCF molecular orbital study on the conformation of serotonin and bufotenine

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Ab initio SCF molecular orbital computations on the conformation of cationic serotonin and bufotenine indicate a preference for a perpendicular, or nearly so, arrangement of the ethylamine side chain with respect to the ring. The planar extended forms observed, among others, in the crystals of cationic indolealkylamines do not represent intrinsically stable conformations of these molecules. Their occurrence must be attributed to the effect of environmental forces.

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  1. 1.

    Pullman,B., Courrière,Ph., Berthod,H.: J. Med. Chem., in press

  2. 2.

    Hehre,W.G., Lathan,W.A., Ditchfield,R., Newton,M.D., Pople,J.A.: Submitted to Q.C.P.E.

  3. 3.

    Hehre,W.G., Stewart,R.F., Pople,J.A.: J. Chem. Phys., 51, 2657 (1969)

  4. 4.

    Port,G.N.J., Pullman,A.: J. Amer. Chem. Soc. 95, 4059 (1973)

  5. 5.

    Pullman,A., Port,G.N.J.: Theoret. Chim. Acta (Berl.) 32, 77 (1973)

  6. 6.

    Pullman,B., Port,G.N.J.: Mol. Pharm., in press

  7. 7.

    Courrière,Ph., Coubeils,J.L., Pullman,B.: Compt. Rend. Acad. Sci. Paris 272, 1697 (1971)

  8. 8.

    Kier,L.B.: J. Pharm. Sci. 57, 1188 (1968)

  9. 9.

    Kang,S., Johnson,C.L., Green,J.P.: J. Mol. Struct. 15, 453 (1973)

  10. 10.

    Falkenberg,G., Carlström,D.: Acta Cryst. 827, 411 (1971)

  11. 11.

    Karle,I.L., Dragonnette,K.S., Brenner,S.A.: Acta Cryst. 19, 713 (1965)

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This work was supported by the A.T.P. N ° A. 655-2303 of the C.N.R.S.

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Port, G.N.J., Pullman, B. An ab initio SCF molecular orbital study on the conformation of serotonin and bufotenine. Theoret. Chim. Acta 33, 275–278 (1974).

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Key words

  • Serotonin
  • Bufotenine