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Weber HP, Petcher TJ. 
“Crystal Structures of the Teonanacatl Hallucinogens. Part I. Psilocybin C13H17N2O4P”. 
J Chem Soc Perkin. 1974;Transactions II:942-946.
Variable temperature n.m.r .• together with vibrational spectroscopy and dipole moments. ·allow ci'etinition of conformational equilibria of substituted hexahydro-1,2,4,5-tetrazines. The tetramethyl erivative (1) exists as a rapidly interconverting mixture of monoaxial (12) 70% and noncentrosymmetric diaxial (1 W) 30%. The tetraethyl derivative (2) exists as rapidly interconverting (22) 33% and (2W) 2% together with the centrosymmetric diaxial (2X) 65%. The bicyclic dimethyl derivative (5) closely resembles (1 ). The tricyclic unsaturated compound (4) exists 8$ the monoaxial ( 42) 67%. the centrosymmetric diaxial ( 4X) 20%, and the tetraequatorial ( 4Y) 13%.

The tricyclic Saturated compound (6) exists mainly in the tetraequatorial conformer (6Y).
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