THE Pictet–Spengler reaction is a special example of the Mannich reaction involving condensation of β-aryl-ethylamines with carbonyl compounds1. In the case of phenylethylamines the resulting products would be 1,2,3,4-tetrahydroisoquinolines, which are particularly interesting because they could be formed from endogenous biogenic amines. The synthesis of simple tetra-hydroisoquinolines in physiological conditions which occur in plants was described in 19342. The facility of this chemical reaction between dopamine and acetaldehyde in conditions which exist in both plants3 and animals4,5 has been confirmed. Because acetaldehyde is the primary metabolite of ethanol, it has been suggested that tetra-hydroisoquinolines are formed in mammals after the ingestion of alcohol4–6. Indeed, this reaction forms the basis for the histochemical localization of catecholamines in nerve tissue for which formaldehyde vapour is used as the carbonyl agent. Reaction products of this type have been demonstrated in animals after administration of methanol7.
Subscribe to Journal
Get full journal access for 1 year
only $3.90 per issue
All prices are NET prices.
VAT will be added later in the checkout.
Rent or Buy article
Get time limited or full article access on ReadCube.
All prices are NET prices.
Whaley, W. M., and Govindachari, T. R., in Organic Reactions (edit. by Adams, R.), 6, 151 (Wiley, New York, 1951).
Schöpf, C., and Bayerle, H., Ann. Chem., 513, 190 (1934).
Kovács, O., and Fodor, G., Chem. Ber., 84, 795 (1951).
Robbins, J. H., Clin. Res., 16, 554 (1968).
Robbins, J. H., Clin. Res., 16, 350 (1968).
Cohen, G., and Collins, M., Science, 167, 1749 (1970).
Cohen, G., and Barrett, R., Fed. Proc., 28, 289 (1969).
Cashaw, J. L., Walsh, M. J., Yamanaka, Y., and Davis, V. E., in Advances in Chromatography (edit. by Zlatkis, A.) (Preston Technical Abstracts, Evanston, Illinois, in the press).
Davis, V. E., and Walsh, M. J., Science, 167, 1005 (1970).
Raskin, N. H., and Sokoloff, L., Science, 162, 131 (1968).
Deitrich, R. A., Biochem. Pharmacol., 15, 1911 (1966).
Jacobsen, E., Pharmacol. Rev., 4, 107 (1952).
Truitt, jun., E. B., and Walsh, M. J., in The Biology of Alcohol I Biochem. (edit. by Kissin, B.) (Pergamon, New York, in the press).
Walsh, M. J., and Truitt, jun., E. B., Fed. Proc., 27, 601 (1968).
Hjort, A. M., de Beer, E. J., and Fassett, R. W., J. Pharmacol. Exp. Therap., 62, 195 (1938).
Fassett, D. W., and Hjort, A. M., J. Pharmacol. Exp. Therap., 63, 253 (1938).
Hjort, A. M., de Beer, E. J., Buck, J. S., and Randall, L. O., J. Pharmacol. Exp. Therap., 76, 263 (1942).
Tóth, E., Fassina, G., and Soncin, E. S., Arch. Intern. Pharmacodynam., 169, 375 (1967).
About this article
Cite this article
YAMANAKA, Y., WALSH, M. & DAVIS, V. Salsolinol, an Alkaloid Derivative of Dopamine formed in vitro during Alcohol Metabolism. Nature 227, 1143–1144 (1970) doi:10.1038/2271143a0
Biochemical Pharmacology (2019)
Molecular modeling of salsolinol, a full G i protein agonist of the μ‐opioid receptor, within the receptor binding site
Chemical Biology & Drug Design (2019)
Neuroscience Letters (2018)
Journal of Experimental Neuroscience (2016)
Key role of salsolinol in ethanol actions on dopamine neuronal activity of the posterior ventral tegmental area
Addiction Biology (2015)