1,2-dehydrosalsolinol profile

1,2-Dehydrosalsolinol (1,2-DHS) is a tetrahydroisoquinoline alkaloid that has been implicated in the pathogenesis of Parkinson's disease. It is formed in the brain by a non-enzymatic reaction between dopamine and salsolinol, which is a naturally occurring compound found in the human brain. 1,2-DHS is thought to be neurotoxic, and it has been shown to induce oxidative stress and mitochondrial dysfunction in neuronal cells. Studies have shown that 1,2-DHS can also interfere with the metabolism of dopamine, leading to its accumulation and further neurotoxicity. The formation of 1,2-DHS is thought to be enhanced by factors such as aging, exposure to toxins, and oxidative stress. Because of its potential role in Parkinson's disease, 1,2-DHS has been extensively studied in both animal and human models. Research has focused on understanding its mechanisms of toxicity, identifying potential therapeutic targets, and developing strategies to prevent or reduce its formation. The compound is the subject of ongoing research, and its potential implications for Parkinson's disease and other neurodegenerative disorders are still being investigated.'

1,2-dehydrosalsolinol: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	20844
CHEMBL ID	60503
CHEBI ID	178978
SCHEMBL ID	18932930
MeSH ID	M0146168

Synonym
1,2-dehydrosalsolinol
1-methyl-3,4-dihydroisoquinoline-6,7-diol
4602-81-7
CHEBI:178978
dsal
CHEMBL60503
6,7-isoquinolinediol, 3,4-dihydro-1-methyl-
139080-83-4
AKOS024370379
SCHEMBL18932930
1-methyl-6,7-dihydroxy-3,4-dihydroisoquinolines
3,4-dihydro-1-methyl-6,7-isoquinolinediol
1-methyl-3,4-di-hydro-6,7-isoquinolinediol
DTXSID20963486
7-hydroxy-1-methyl-3,4-dihydroisoquinolin-6(2h)-one

Class	Description
isoquinolines	A class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Assay ID	Title	Year	Journal	Article
AID1617016	Agonist activity at human alpha1 beta adrenergic receptor expressed in CHOK1 cells co-expressing Galpha15 assessed as increase in calcium influx by measuring fluorescence intensity at 100 uM by FLIPR assay relative to epinephrine
AID1617015	Agonist activity at human beta1 adrenergic receptor expressed in CHOK1 cells co-expressing Galpha15 assessed as increase in calcium influx by measuring fluorescence intensity at 100 uM by FLIPR assay relative to epinephrine
AID1404506	Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production measured after 24 hrs by Griess assay
AID116894	Compound was evaluated for its lethal dose (LD50) by dissolving in 5 microL of isotonic saline and injected intracranially in mice which resulted in the death of 50% of the treated animals within 1 hour	1993	Journal of medicinal chemistry, Jan-08, Volume: 36, Issue:1	Oxidation chemistry of the endogenous central nervous system alkaloid salsolinol-1-carboxylic acid.
AID1404507	Agonist activity at human beta2-AR expressed in CHOK1 cells co-expressing Galpha15 at 100 uM measured after 21 secs to 120 secs by Calcium-4 dye based FLIPR assay relative to 1 uM isoproterenol
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (18.18)	18.7374
1990's	5 (45.45)	18.2507
2000's	0 (0.00)	29.6817
2010's	3 (27.27)	24.3611
2020's	1 (9.09)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	11 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents.	1.97	1	catechols; dihydroxyphenylacetic acid	human metabolite
vanilmandelic acid Vanilmandelic Acid: A 3-O-methyl ether of 3,4-dihydroxymandelic acid. It is an end-stage metabolite of CATECHOLAMINES; EPINEPHRINE; and NOREPINEPHRINE.. vanillylmandelic acid : An aromatic ether that is the 3-O-methyl ether of 3,4-dihydroxymandelic acid.	1.98	1	2-hydroxy monocarboxylic acid; aromatic ether; phenols	human metabolite
3-methoxytyrosine [no description available]	1.98	1	tyrosine derivative
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.	2.38	2	guaiacols; monocarboxylic acid	human metabolite; mouse metabolite
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5.	1.97	1	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
benserazide Benserazide: An inhibitor of DOPA DECARBOXYLASE that does not enter the central nervous system. It is often given with LEVODOPA in the treatment of parkinsonism to prevent the conversion of levodopa to dopamine in the periphery, thereby increasing the amount that reaches the central nervous system and reducing the required dose. It has no antiparkinson actions when given alone.. benserazide : A carbohydrazide that results from the formal condensation of the carboxy group of DL-serine with the primary amino group of 4-(hydrazinylmethyl)benzene-1,2,3-triol. An aromatic-L-amino-acid decarboxylase inhibitor (DOPA decarboxylase inhibitor) that does not enter the central nervous system, it is used as its hydrochloride salt as an adjunct to levodopa in the treatment of parkinsonism. By preventing the conversion of levodopa to dopamine in the periphery, it causes an increase in the amount of levodopa reaching the central nervous system and so reduces the required dose. Benserazide has no antiparkinson actions when given alone.	2.38	2	carbohydrazide; catechols; primary alcohol; primary amino compound	antiparkinson drug; dopaminergic agent; EC 4.1.1.28 (aromatic-L-amino-acid decarboxylase) inhibitor
papaverine Papaverine: An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels.. papaverine : A benzylisoquinoline alkaloid that is isoquinoline substituted by methoxy groups at positions 6 and 7 and a 3,4-dimethoxybenzyl group at position 1. It has been isolated from Papaver somniferum.	1.97	1	benzylisoquinoline alkaloid; dimethoxybenzene; isoquinolines	antispasmodic drug; vasodilator agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	1.97	1	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	1.98	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
1,2,3,4-tetrahydroisoquinoline 1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified	1.98	1	isoquinolines
hydrazine diamine : Any polyamine that contains two amino groups.	1.97	1	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
methoxyhydroxyphenylglycol Methoxyhydroxyphenylglycol: Synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover.	1.98	1	methoxybenzenes; phenols
tetrahydropapaveroline Tetrahydropapaveroline: A leukomaine (animal alkaloid) formed in brain and liver from dopamine and L-dopa; it may be implicated in psychiatric problems.	1.97	1	benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; isoquinolinol	human metabolite
n-methylisoquinolinium N-methylisoquinolinium: RN given refers to parent cpd; structure given in first source	1.98	1
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.11	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
norsalsolinol norsalsolinol: rigid dopamine analog; RN given refers to parent cpd; structure. norsalsolinol : An isoquinolinol that is 1,2,3,4-tetrahydroisoquinoline substituted by hydroxy groups at positions 6 and 7. It is present in the dopamine-rich areas of the human brain, including the substantia nigra.	2.38	2	isoquinolinol	animal metabolite; apoptosis inducer; human metabolite; marine metabolite
salsolinol salsolinol: RN given refers to cpd without isomeric designation; EP to SALSOLINE ALKALOIDS (78-82); on-line search SALSOLINE ALKALOIDS (78-82); Index Medicus search ISOQUINOLINES (78-82). (S)-salsolinol : A 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol that has S-configuration.	2.89	4	1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol	human urinary metabolite
1-methyl-1,2,3,4-tetrahydroisoquinoline 1-methyl-1,2,3,4-tetrahydroisoquinoline: endogenous amine from rat brain	1.98	1	isoquinolines
1-carboxysalsolinol 1-carboxysalsolinol: RN given refers to cpd without isomeric designation	2.37	2
ro 8-0576 benserazide, levodopa drug combination: combination of L-Dopa and seryltrihydroxybenzylhydrazine; used in treatment of parkinsonism	1.97	1
nadp [no description available]	1.97	1
n-(2-pyridone-6-yl)-n',n'-di-n-propylformamidine N-(2-pyridone-6-yl)-N',N'-di-n-propylformamidine: inhibitor of cerebral catechol O-methylation; structure given in first source	1.98	1	pyridone

Condition	Indicated	Relationship Strength	Studies	Trials
Idiopathic Parkinson Disease [description not available]	0	1.98	1	0
Parkinson Disease A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)	0	1.98	1	0

1,2-dehydrosalsolinol

Description

Cross-References

Synonyms (15)

Drug Classes (1)

Bioassays (5)

Research

Studies (11)

Market Indicators

Research Demand Index: 12.38

Study Types