Theoretica chimica acta

, Volume 33, Issue 3, pp 275–278 | Cite as

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

  • G. N. J. Port
  • B. Pullman


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.

Key words

Serotonin Bufotenine 


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  1. 1.
    Pullman,B., Courrière,Ph., Berthod,H.: J. Med. Chem., in pressGoogle Scholar
  2. 2.
    Hehre,W.G., Lathan,W.A., Ditchfield,R., Newton,M.D., Pople,J.A.: Submitted to Q.C.P.E.Google Scholar
  3. 3.
    Hehre,W.G., Stewart,R.F., Pople,J.A.: J. Chem. Phys., 51, 2657 (1969)Google Scholar
  4. 4.
    Port,G.N.J., Pullman,A.: J. Amer. Chem. Soc. 95, 4059 (1973)Google Scholar
  5. 5.
    Pullman,A., Port,G.N.J.: Theoret. Chim. Acta (Berl.) 32, 77 (1973)Google Scholar
  6. 6.
    Pullman,B., Port,G.N.J.: Mol. Pharm., in pressGoogle Scholar
  7. 7.
    Courrière,Ph., Coubeils,J.L., Pullman,B.: Compt. Rend. Acad. Sci. Paris 272, 1697 (1971)Google Scholar
  8. 8.
    Kier,L.B.: J. Pharm. Sci. 57, 1188 (1968)Google Scholar
  9. 9.
    Kang,S., Johnson,C.L., Green,J.P.: J. Mol. Struct. 15, 453 (1973)Google Scholar
  10. 10.
    Falkenberg,G., Carlström,D.: Acta Cryst. 827, 411 (1971)Google Scholar
  11. 11.
    Karle,I.L., Dragonnette,K.S., Brenner,S.A.: Acta Cryst. 19, 713 (1965)Google Scholar

Copyright information

© Springer-Verlag 1974

Authors and Affiliations

  • G. N. J. Port
    • 1
  • B. Pullman
    • 1
  1. 1.Institut de Biologie Physico-ChimiqueLaboratoire de Chimie Théorique associé au C.N.R.S.Paris

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