Salsolinol, free of isosalsolinol, exerts ethanol-like motivational/sensitization effects leading to increases in ethanol intake

Quintanilla, Marı́a Elena; Rivera-Meza, Mario; Berríos-Cárcamo, Pablo; Bustamante, Diego; Buscaglia, Marianne; Morales, Paola; Karahanian, Eduardo; Herrera‐Marschitz, Mario; Israel, Yedy

doi:10.1016/j.alcohol.2014.07.003

Cited by 39 publications

(48 citation statements)

References 30 publications

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“…The finding by Rojkovicova et al (2008) that both enantiomers are increased following ethanol consumption is in line with a spontaneous non-enzymatic synthesis of salsolinol (King et al 1974;Deng et al 1995). It is noted that in the present study (R)-SAL qualitatively replicates the effects that have been reported were produced by (RS)-SAL administered intra-VTA on conditioned place preference (Hipólito et al 2011;Quintanilla et al 2014), locomotor sensitization (Hipólito et al 2010;Quintanilla et al 2014) and voluntary ethanol intake (Quintanilla et al 2014).…”

Section: Discussionsupporting

confidence: 88%

“…Thus, clear physiological effects are observed when only one side is injected. In line with this view, in a previous study (Quintanilla et al 2014), we injected unilaterally the same dose of (RS)-SAL (30 pmol) that (Hipólito et al 2010(Hipólito et al , 2011 had injected bilaterally, obtaining the same results on locomotor activity and CPP.…”

Section: Drug Microinjection Proceduressupporting

confidence: 80%

“…Racemic (RS)-SAL, free of isosalsolinol (Quintanilla et al 2014), was purchased from Santa Cruz Biotechnology (sc-215838; reporting 98 percent purity) (Dallas, TX, USA). Ammonium acetate was from Merck (Darmstadt, Germany) and triethylamine was from Sigma (St. Louis, MO, USA).…”

Section: Drugs and Solutionsmentioning

confidence: 99%

“…(a) Locomotor activity. It was evaluated as previously described (Quintanilla et al 2014) in an open-field chamber (75 × 75 × 30 cm). Before testing locomotor activity, animals were handled for 5 minutes per day for 4 days.…”

Section: Experiments 3 Effect Of Repeated Intra-vta Injections Of (R)mentioning

confidence: 99%

“…In addition, (3) SAL significantly increased locomotor activity (Quintanilla et al 2014). The possibility exists that only one, the (R)-or (S)-SAL enantiomer, might induce motivational effects, locomotor sensitization and promotion of ethanol consumption.…”

Section: Introductionmentioning

confidence: 99%

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(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake

et al. 2015

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Ethanol is oxidized in the brain to acetaldehyde, which can condense with dopamine to generate (R/S)-salsolinol [(RS)-SAL]. Racemic salsolinol [(RS)-SAL] is self-infused by rats into the posterior ventral tegmental area (VTA) at significantly lower concentrations than those of acetaldehyde, suggesting that (RS)-SAL is a most active product of ethanol metabolism. Early studies showed that repeated intraperitoneal or intra-VTA administration of (RS)-SAL (10 mg/kg) induced conditioned place preference, led to locomotor sensitization and increased voluntary ethanol consumption. In the present study, we separated the (R)- and (S)-enantiomers from a commercial (RS)-SAL using a high-performance liquid chromatography with electrochemical detection system fitted with a β-cyclodextrin-modified column. We injected (R)-SAL or (S)-SAL (30 pmol/1.0 μl) into the VTA of naïve UChB rats bred as alcohol drinkers to study whether one or both SAL enantiomers are responsible for the motivated behavioral effects, sensitization and increase in voluntary ethanol intake. The present results show that repeated administration of (R)-SAL leads to (1) conditioned place preference; (2) locomotor sensitization; and (3) marked increases in binge-like ethanol intake. Conversely, (S)-SAL did not influence any of these parameters. Overall, data indicate that (R)-SAL stereospecifically induces motivational effects, behavioral sensitization and increases ethanol intake.

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Section: Discussionsupporting

confidence: 88%

Section: Drug Microinjection Proceduressupporting

confidence: 80%

Section: Drugs and Solutionsmentioning

confidence: 99%

Section: Experiments 3 Effect Of Repeated Intra-vta Injections Of (R)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake

et al. 2015

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Theoretical insights into the regioselectivity of a Pictet-Spengler reaction: Transition state structures leading to salsolinol and isosalsolinol

Almodóvar

Rezende

Cassels

et al. 2016

J. Phys. Org. Chem.

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The mechanism of the cyclization step of the Pictet‐Spengler reaction between acetaldehyde and dopamine to give salsolinol and isosalsolinol was studied computationally, using density functional theory. The preferential formation in acidic media of salsolinol, the product of para‐cyclization, and the requirement of a neutral pH for the formation of the ortho‐cyclized isosalsolinol are explained in terms of 2 different mechanistic routes with an iminium ion or a phenolate‐iminium zwitterion as starting reactants.

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Molecular Imaging Studies of Alcohol Use Disorder

Bach

Timary

Gründer

et al. 2023

Current Topics in Behavioral Neurosciences

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Salsolinol, free of isosalsolinol, exerts ethanol-like motivational/sensitization effects leading to increases in ethanol intake

Cited by 39 publications

References 30 publications

(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake

(R)-Salsolinol, a product of ethanol metabolism, stereospecifically induces behavioral sensitization and leads to excessive alcohol intake

Theoretical insights into the regioselectivity of a Pictet-Spengler reaction: Transition state structures leading to salsolinol and isosalsolinol

Molecular Imaging Studies of Alcohol Use Disorder

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