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. 1969 Aug;63(4):1063–1070. doi: 10.1073/pnas.63.4.1063

ON THE CONFORMATIONS OF HALLUCINOGENIC MOLECULES AND THEIR CORRELATION

Cyrus Chothia 1,2, Peter Pauling 1,2
PMCID: PMC223427  PMID: 4311249

Abstract

There are only a few possible conformations of D-lysergic acid diethylamide and hallucinogenic derivatives of tryptamine and phenylethylamine. Of these possible conformations there is a high structural correlation among the probable conformations of active hallucinogenic molecules and between these conformations and the known conformations of several central nervous system transmitter molecules.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. BALESTRIERI A., FONTANARI D. Acquired and crossed tolerance to mescaline, LSD-25, and BOL-148. AMA Arch Gen Psychiatry. 1959 Sep;1:279–282. doi: 10.1001/archpsyc.1959.03590030063008. [DOI] [PubMed] [Google Scholar]
  2. Canepa F. G., Pauling P., Sörum H. Structure of acetylcholine and other substrates of cholinergic systems. Nature. 1966 May 28;210(5039):907–909. doi: 10.1038/210907a0. [DOI] [PubMed] [Google Scholar]
  3. Carlström D., Bergin R. The structure of the catecholamines. I. The crystal structure of noradrenaline hydrochloride. Acta Crystallogr. 1967 Aug 10;23(2):313–319. doi: 10.1107/s0365110x67002646. [DOI] [PubMed] [Google Scholar]
  4. Chothia C., Pauling P. Conformations of acetylcholine. Nature. 1968 Sep 14;219(5159):1156–1157. doi: 10.1038/2191156a0. [DOI] [PubMed] [Google Scholar]
  5. Colomo F., Rahamimoff R., Stefani E. An action of 5-hydroxytryptamine on the frog motor end-plate. Eur J Pharmacol. 1968 Jun;3(3):272–274. doi: 10.1016/0014-2999(68)90143-x. [DOI] [PubMed] [Google Scholar]
  6. GIARMAN N. J., FREEDMAN D. X. BIOCHEMICAL ASPECTS OF THE ACTIONS OF PSYCHOTOMIMETIC DRUGS. Pharmacol Rev. 1965 Mar;17:1–25. [PubMed] [Google Scholar]
  7. HEY P. On relationships between structure and nicotine-like stimulant activity in choline esters and ethers. Br J Pharmacol Chemother. 1952 Mar;7(1):117–129. doi: 10.1111/j.1476-5381.1952.tb00697.x. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. HORITA A. Some biochemical studies on psilocybin and psilogin. J Neuropsychiatr. 1963 Apr;4:270–273. [PubMed] [Google Scholar]
  9. Hamilton J. A., Steinrauf L. K. Crystallographic studies of iodine-containing amino acids. I. Di-iodo-L-tyrosine dihydrate. Acta Crystallogr. 1967 Nov 10;23(5):817–825. doi: 10.1107/s0365110x67003743. [DOI] [PubMed] [Google Scholar]
  10. ISBELL H., WOLBACH A. B., WIKLER A., MINER E. J. Cross tolerance between LSD and psilocybin. Psychopharmacologia. 1961;2:147–159. doi: 10.1007/BF00407974. [DOI] [PubMed] [Google Scholar]
  11. KARREMAN G., ISENBERG I., SZENT-GYORGYI A. On the mechanism of action of chlorpromazine. Science. 1959 Oct 30;130(3383):1191–1192. doi: 10.1126/science.130.3383.1191. [DOI] [PubMed] [Google Scholar]
  12. Karle I. L., Dragonette K. S., Brenner S. A. The crystal and molecular structure of the serotonin-creatinine sulphate complex. Acta Crystallogr. 1965 Nov 10;19(5):713–716. doi: 10.1107/s0365110x65004267. [DOI] [PubMed] [Google Scholar]
  13. SCHOPP R. T., KREUTTER W. F., GUZAK S. V. Neuromyal blocking action of mescaline. Am J Physiol. 1961 Jun;200:1226–1228. doi: 10.1152/ajplegacy.1961.200.6.1226. [DOI] [PubMed] [Google Scholar]
  14. Shulgin A. T., Sargent T., Naranjo C. Structure--activity relationships of one-ring psychotomimetics. Nature. 1969 Feb 8;221(5180):537–541. doi: 10.1038/221537a0. [DOI] [PubMed] [Google Scholar]
  15. Snyder S. H., Merril C. R. A relationship between the hallucinogenic activity of drugs and their electronic configuration. Proc Natl Acad Sci U S A. 1965 Jul;54(1):258–266. doi: 10.1073/pnas.54.1.258. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Snyder S. H., Richelson E. Psychedelic drugs: steric factors that predict psychotropic activity. Proc Natl Acad Sci U S A. 1968 May;60(1):206–213. doi: 10.1073/pnas.60.1.206. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Stefani E., Gerschenfeld H. M. Comparative study of acetylcholine and 5-hydroxytryptamine receptors on single snail neurons. J Neurophysiol. 1969 Jan;32(1):64–74. doi: 10.1152/jn.1969.32.1.64. [DOI] [PubMed] [Google Scholar]
  18. Takigawa T., Ashida T., Sasada Y., Kakudo M. The crystal structures of L-tryptophan hydrochloride and hydrobromide. Bull Chem Soc Jpn. 1966 Nov;39(11):2369–2378. doi: 10.1246/bcsj.39.2369. [DOI] [PubMed] [Google Scholar]

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