Abstract
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.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
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).
Author information
Authors and Affiliations
Rights and permissions
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). https://doi.org/10.1038/2271143a0
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1038/2271143a0
This article is cited by
-
Ethanol and tetrahydroisoquinoline alkaloids do not produce narcotic discriminative stimulus effects
Psychopharmacology (1983)
-
Effects of tetrahydropapaveroline and salsolinol on cerebral monoamine metabolism and their interactions with psychopharmacological drugs
Naunyn-Schmiedeberg's Archives of Pharmacology (1979)
-
Isoquinoline alkaloids
Neurochemical Research (1978)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.