(R)-Salsolinol

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(R)-Salsolinol
2D structure for (R)-Salsolinol
Chemical Name	1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Chemical Formula	C₁₀H₁₃NO₂
CAS Number	525-72-4
Chemical Information	HMDB05199
Biochemical Taxonomy	Catecholamines and Derivatives
Functional Taxonomy	Not Available
Nutritional Taxonomy	Not Available
Metabolic Pathways	Not Available
Biofluid Location	Blood Cerebrospinal Fluid (CSF)
Tissue Location	Not Available
Normal Biofluid Concentrations	Blood: 0.00042 +/- 0.000094 umol/L Cerebrospinal Fluid (CSF): 0.005 +/- 0.002 (0.003 - 0.00748) uM
Normal Tissue Concentrations	Not Available
Diseases / Conditions Related to Nutrition	Hypertensive patients Multiple System Atrophy (MSA) Parkinson's disease
Other (Monogenic Disorders)	Not Available
Abnormal Biofluid Concentrations	Blood (Hypertensive patients): 0.0010 +/- 0.00043 umol/L Cerebrospinal Fluid (CSF) (Multiple System Atrophy (MSA)): 0.004 +/- 0.001 (0.002-0.005) uM Cerebrospinal Fluid (CSF) (Parkinson's disease): 0.005 +/- 0.001 (0.003-0.006) uM
Abnormal Tissue Concentrations	Not Available
Physiological Processes	Not Available

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Introduction

guidelines
Salsolinol is an endogenous catechol isoquinoline detected in humans. Salsolinol was detected in urine of parkinsonian patients administered with L-DOPA. This finding stimulated the studies on Salsolinol derivatives in the brain, and gave new aspects of the endogenous alkaloids, which had been considered to occur only in plants. In normal non-alcoholic subjects and alcoholics, Salsolinol and O-methylated Salsolinol were found in urine, cerebrospinal fluid and brains. Salsolinol has an asymmetric center at first position and exists as (R)- and (S)enantiomer. The (R)enantiomer of Salsolinol is predominant in urine from healthy volunteers. Only the (R)enantiomers of Salsolinol and N-methylated Salsolinol occur in the human brain, cerebrospinal fluid (CSF) and intraventricular fluid (IVF), and the (S)enantiomers were not detected. (R)salsolinol synthase catalyzes the enantio-selective synthesis of (R)Salsolinol and 1-carboxyl(R)Salsolinol from dopamine with acetaldehyde or pyruvic acid. The N-methylation of (R)salsolinol into N-methylsalsolinol (NMSal) is catalyzed by two N-methyltransferases with different optimum pH, at pH 7.0 and 8.4. NM(R)Salsolinol is enzymatically oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion (DMDHIQ+) by an oxidase sensitive to semicarbaside and also non-enzymatically by autoxidation. NM(R)Salsolinol and its precursor, dopamine, were found to occur selectively in the nigro-striatum, whereas (R)Salsolinol distributes uniformly among the brain regions. (PMID 14697894)