Salsolinol, an Alkaloid Derivative of Dopamine formed in vitro during Alcohol Metabolism

Identification of 4-methylspinaceamine - a Pictet – Spengler condensation reaction product of histamine with acetaldehyde - in human urine

“…Several reports suggested that the presence of MTBCs and SAL in mammalian tissues and fluid samples was due to the in vivo condensation of AA with indoleamines or dopamine (MacIsaac, 1961;Cohen and Collins, 1970;Yamanaka et al, 1970;Collins et al, 1979;Callaway et al, 1996;Musshoff et al, 2000;Foppoli et al, 2002;Jamal et al, 2003), since these reactions can take place under physiological conditions. We previously reported that AA had much higher reactivity towards histamine than indoleamines under physiological conditions and the reaction gave only one product, 4-MSPA, in good yield (Ohya and Niitsu, 2003).…”

“…The reactions of AA with indoleamines and dopamine have been extensively documented (Whaley and Govindachari, 1951;MacIsaac, 1961;Cohen and Collins, 1970;Herraiz and Ough, 1993;Callaway et al, 1994Callaway et al, , 1996Cox and Cook, 1995;Foppoli et al, 2002). Several reports suggested that the presence of MTBCs and SAL in mammalian tissue and fluid samples was caused by the reaction of AA with indoleamines and dopamine in vivo (MacIsaac, 1961;Cohen and Collins, 1970;Yamanaka et al, 1970;Collins et al, 1979;Callaway et al, 1996;Musshoff et al, 2000;Foppoli et al, 2002;Jamal et al, 2003) since the condensation reactions readily occur under physiological conditions (Whaley and Govindachari, 1951;MacIsaac, 1961;Cohen and Collins, 1970;Callaway et al, 1994Callaway et al, , 1996Foppoli et al, 2002). On the other hand, Tsuchiya et al proposed that most fractions of MTBCs found in human urine were exogenously supplied via dietary sources (Tsuchiya et al, 1996a(Tsuchiya et al, , 1996b.…”

Alcohol dehydrogenase alleles in Parkinson's disease

“…Dopamine neurons may be especially sensitive to aldehyde toxicity because of the ability of dopamine to condense with acetaldehyde to form the neurotoxin salsolinol, a substance related to the PDinducing agent MPTP. 25 Salsolinol has been found to be present in higher concentrations in the cerebrospinal fluid of untreated patients with PD than of control patients or patients with multiple system atrophy. 26 The high contents of aldehyde dehydrogenase in dopamine neurons may provide a defense mechanism against such toxicity.…”

Catechol-O-methyltransferase: potential relationship to idiopathic hypertension

“…The intimate and interactive coupling of “morphinergic” to dopaminergic behavioral processes provide a cogent window of understanding additive behavioral processes. For example, initial speculation as to the existence and potential physiological role of endogenous morphine were made over 30 years ago by prominent researchers in the field of alcohol abuse, not opiate abuse, who advanced the hypothesis that the reinforcing or additive effects of ethanol were functionally linked to the cellular effects of DA derived isoquinoline alkaloids, notably the tetrahydroisoquinoline salsolinol [32–34] and the benzylisoquinoline morphine precursor tetrahydropapaveroline (THP) [35–37]. Recognition of tetrahydroisoquinolines, THP, and endogenous morphine as active principles of alcohol abuse was inherently linked to their normal presence in dopaminergic neurons, enhanced cellular expression following chronic ethanol intake [37–42], and concentration-dependent disregulation of DA metabolism and/or dopaminergic signaling in mesolimbic/mesocortical areas such as the nucleus accumbens and the ventral tegmental area traditionally associated with reward and reinforcement of ethanol intake [15, 16, 43–51].…”