Tetrahydroisoquinolines: A review

Ysern, Maria E. Zarranz De; Ordóñez, Luis A.

doi:10.1016/0364-7722(81)90085-0

Cited by 31 publications

(10 citation statements)

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“…In most cases, tetrahydroisoquinolines can be formed as condensation products of biogenic amines (i.e., phenylethylamines and catecholamines) with aldehydes or α-keto acids by the so-called Pictet–Spengler reaction (Rommelspacher and Susilo 1985; Zarranz de Ysern and Ordonez 1981; Nagatsu 1997; McNaught et al 1998), although some of them may be also synthesized enzymatically (Yamakawa and Ohta 1997, 1999; Naoi et al 2004). The tetrahydroisoquinoline family can be divided into compounds with catechol- and non-catechol structure.…”

Section: Introductionmentioning

confidence: 99%

1-Methyl-1,2,3,4-Tetrahydroisoquinoline, an Endogenous Amine with Unexpected Mechanism of Action: New Vistas of Therapeutic Application

2013

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This review outlines the effects of 1,2,3,4-tetrahydroisoquinoline (TIQ) and its derivative, 1-methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ), endogenous substances imbued with high pharmacological potential and broad spectrum of action in brain. 1MeTIQ has gained special interest as a neuroprotectant, and its ability to antagonize the behavioral syndrome produced by well-known neurotoxins (e.g., MPTP; rotenone). This review is thus focused on mechanisms of action of 1MeTIQ in behavioral, neurochemical, and molecular studies in rodents; also, effects of TIQ and 1MeTIQ on dopamine metabolism; and neuroprotective properties of TIQ and 1MeTIQ in vitro and in vivo. Finally, antiaddictive properties of 1MeTIQ will be described in cocaine self-administered rats. Findings implicate TIQ and especially its methyl derivative 1MeTIQ in unique and complex mechanisms of neuroprotection in various neurodegenerative illnesses of the central nervous system. We believe that MAO inhibition, free radicals scavenging properties, and antagonism to the glutamatergic system may play an essential role in neuroprotection. In addition, the results strongly support the view that 1MeTIQ has a considerable potential as a drug for combating substance abuse, through the attenuation of craving.

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Section: Introductionmentioning

confidence: 99%

1-Methyl-1,2,3,4-Tetrahydroisoquinoline, an Endogenous Amine with Unexpected Mechanism of Action: New Vistas of Therapeutic Application

2013

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“…A group of substances present in the human brain and suspected of having neurotoxic activity because of structural similarity to tetrahydropyridines, are simple tetrahydroisoquinolines (Zarranz de Ysern and Ordonez, 1981;Niwa et aL, 1991). The most investigated of those compounds was salsolinol ((R)-l-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline) (Sandier et aL, 1973;Niwa et aL, 1987;Moser and K6mpf 1992), which in mammalian brain is a product of enzymatic condensation of dopamine with acetylaldehyde .…”

Section: Introductionmentioning

confidence: 99%

A possible physiological role for cerebral tetrahydroisoquinolines

Vetulani¹,

Antkiewicz-Michaluk²,

Nalepa³

et al. 2003

neurotox res

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Tetrahydroisoquinolines present in the mammalian brain, 1,2,3,4-tetrahydroisoquinoline (TIQ) and salsolinol, suspected to cause neurodegeneration leading to Parkinson's disease, were investigated to find their possible physiological role. To this aim their behavioral and receptor effects induced after a single dose were tested in mice and rats. Both compounds do not affect significantly the basal locomotor activity, very effectively block hyperactivity induced by apomorphine (rats) and amphetamine (mice), only partially block hyperactivity induced by scopolamine, do not affect locomotor stimulation induced by cocaine, and strongly augment the running fit induced by morphine (mice). They do not produce extrapyramidal symptoms and do not potentiate haloperidol-induced catalepsy (rats). TIQ and salsolinol do not displace antagonists of several receptors (including D(1) and D(2)) from their binding sites, but displace the agonists of Alpha(2)-adrenoceptors, [(3)H]clonidine and of dopamine receptors, [(3)H]apomorphine. The results indicate that salsolinol and TIQ act as specific antagonists of agonistic conformation of dopamine receptors, and owing to that may play a role of endogenous feed-back regulators of the dopaminergic system. Those properties make tetrahydroisoquinolines potential antidopaminergic drugs devoid of extrapyramidal effects, with possible application in substance addiction disorder as anti-craving agents.

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“…The tetrahydroisoquinolines, bearing structural similarity to the hydropyridines (of which MPTP is the best studied neurotoxin), are endogenous to the human brain (Niwa et al, 1991;Zarranz de Ysern and Ordonez, 1981). Salsolinol [1-methyl-6,7-dihydroxy-1,2,3,4tetrahydroisoquinoline], which has been subjected to some degree of investigation (Sandler et al, 1973;Niwa et al, 1987;Moser and Kömpf, 1992), is implicated in PD (Antkiewicz-Michaluk et al, 1997;Naoi et al, 1998a).…”

Section: Endogenous Compounds With Neurotoxic Potentialmentioning

confidence: 99%

Brain sites of movement disorder: Genetic and environmental agents in neurodevelopmental perturbations

et al. 2003

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In assessing and assimilating the neurodevelopmental basis of the so-called movement disorders it is probably useful to establish certain concepts that will modulate both the variation and selection of affliction, mechanisms-processes and diversity of disease states. Both genetic, developmental and degenerative aberrations are to be encompassed within such an approach, as well as all deviations from the necessary components of behaviour that are generally understood to incorporate "normal" functioning. In the present treatise, both conditions of hyperactivity/hypoactivity, akinesia and bradykinesia together with a constellation of other symptoms and syndromes are considered in conjunction with the neuropharmacological and brain morphological alterations that may or may not accompany them, e.g. following neonatal denervation. As a case in point, the neuroanatomical and neurochemical points of interaction in Attention Deficit and Hyperactivity disorder (ADHD) are examined with reference to both the perinatal metallic and organic environment and genetic backgrounds. The role of apoptosis, as opposed to necrosis, in cell death during brain development necessitates careful considerations of the current explosion of evidence for brain nerve growth factors, neurotrophins and cytokines, and the processes regulating their appearance, release and fate. Some of these processes may possess putative inherited characteristics, like alpha-synuclein, others may to greater or lesser extents be endogenous or semi-endogenous (in food), like the tetrahydroisoquinolines, others exogenous until inhaled or injested through environmental accident, like heavy metals, e.g. mercury. Another central concept of neurodevelopment is cellular plasticity, thereby underlining the essential involvement of glutamate systems and N-methyl-D-aspartate receptor configurations. Finally, an essential assimilation of brain development in disease must delineate the relative merits of inherited as opposed to environmental risks not only for the commonly-regarded movement disorders, like Parkinson's disease, Huntington's disease and epilepsy, but also for afflictions bearing strong elements of psychosocial tragedy, like ADHD, autism and Savantism.

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Tetrahydroisoquinolines: A review

Cited by 31 publications

References 50 publications

1-Methyl-1,2,3,4-Tetrahydroisoquinoline, an Endogenous Amine with Unexpected Mechanism of Action: New Vistas of Therapeutic Application

1-Methyl-1,2,3,4-Tetrahydroisoquinoline, an Endogenous Amine with Unexpected Mechanism of Action: New Vistas of Therapeutic Application

A possible physiological role for cerebral tetrahydroisoquinolines

Brain sites of movement disorder: Genetic and environmental agents in neurodevelopmental perturbations

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