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525-72-4 | 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
CAS No: 525-72-4 Catalog No: AG00DJPN MDL No:MFCD00056097
Product Description
Catalog Number:
AG00DJPN
Chemical Name:
1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
CAS Number:
525-72-4
Molecular Formula:
C10H13NO2
Molecular Weight:
179.2157
MDL Number:
MFCD00056097
IUPAC Name:
1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
InChI:
InChI=1S/C10H13NO2/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6/h4-6,11-13H,2-3H2,1H3
InChI Key:
IBRKLUSXDYATLG-UHFFFAOYSA-N
SMILES:
CC1NCCc2c1cc(O)c(c2)O
Properties
Complexity:
186
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
179.095g/mol
Formal Charge:
0
Heavy Atom Count:
13
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
179.219g/mol
Monoisotopic Mass:
179.095g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
52.5A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
1
Literature
| Title | Journal |
|---|---|
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| Salsolinol induced apoptotic changes in neural stem cells: amelioration by neurotrophin support. | Neurotoxicology 20130301 |
| What is in that drink: the biological actions of ethanol, acetaldehyde, and salsolinol. | Current topics in behavioral neurosciences 20130101 |
| Low level of glutathione can intensify the toxic effect of salsolinol in SH-SY5Y neuroblastoma cell line. | Neurotoxicology 20120601 |
| Effects of photoperiod on salsolinol-induced prolactin secretion in goats. | Animal science journal = Nihon chikusan Gakkaiho 20120501 |
| Salsolinol and isosalsolinol: condensation products of acetaldehyde and dopamine. Separation of their enantiomers in the presence of a large excess of dopamine. | Journal of pharmaceutical and biomedical analysis 20120407 |
| Salsolinol stimulates dopamine neurons in slices of posterior ventral tegmental area indirectly by activating μ-opioid receptors. | The Journal of pharmacology and experimental therapeutics 20120401 |
| Hypotensive and cardio-chronotropic constituents of Tinospora crispa and mechanisms of action on the cardiovascular system in anesthetized rats. | Journal of ethnopharmacology 20120306 |
| Salsolinol, a tetrahydroisoquinoline-derived neurotoxin, induces oxidative modification of neurofilament-L protection by histidyl dipeptides. | BMB reports 20120201 |
| Revisiting the controversial role of salsolinol in the neurobiological effects of ethanol: old and new vistas. | Neuroscience and biobehavioral reviews 20120101 |
| Bromocriptine inhibits salsolinol-induced prolactin release in male goats. | Animal science journal = Nihon chikusan Gakkaiho 20120101 |
| Salsolinol facilitates glutamatergic transmission to dopamine neurons in the posterior ventral tegmental area of rats. | PloS one 20120101 |
| Research on an in vitro cell system for testing the neurotoxicity of kynurenine pathway metabolites. | Die Pharmazie 20111101 |
| Induction of conditioned place preference and dopamine release by salsolinol in posterior VTA of rats: involvement of μ-opioid receptors. | Neurochemistry international 20111001 |
| Chip electrophoresis of active banana ingredients with label-free detection utilizing deep UV native fluorescence and mass spectrometry. | Analytical and bioanalytical chemistry 20110201 |
| Isolation of salsolinol, a tetrahydroisoquinoline alkaloid, from the marine sponge Xestospongia cf. vansoesti as a proteasome inhibitor. | Chemical & pharmaceutical bulletin 20110101 |
| The influence of salsolinol on dopaminergic system activity within the mediobasal hypothalamus of anestrous sheep: a model for studies on the salsolinol-dopamine relationship. | Acta neurobiologiae experimentalis 20110101 |
| The effects of salsolinol on the mucosal mast cells in the rat gut. | Folia medica Cracoviensia 20110101 |
| Opioid-salsolinol relationship in the control of prolactin release during lactation. | Neuroscience 20101110 |
| Characteristics of prolactin-releasing response to salsolinol in vivo in cattle. | Domestic animal endocrinology 20100701 |
| Determination of salsolinol, norsalsolinol, and twenty-one biogenic amines using micellar electrokinetic capillary chromatography-electrochemical detection. | Electrophoresis 20100601 |
| Locomotor stimulant effects of acute and repeated intrategmental injections of salsolinol in rats: role of mu-opioid receptors. | Psychopharmacology 20100301 |
| A critical evaluation of influence of ethanol and diet on salsolinol enantiomers in humans and rats. | Alcoholism, clinical and experimental research 20100201 |
| Effects of a structural analogue of salsolinol, 1-MeDIQ, on pituitary prolactin release and dopaminergic activity in the mediobasal hypothalamus in nursing sheep. | Brain research 20100111 |
| Effects of salsolinol and its antagonistic analogue, 1-MeDIQ, on growth hormone release in nursing sheep. | Acta neurobiologiae experimentalis 20100101 |
| Different mechanisms of NMDA-mediated protection against neuronal apoptosis: a stimuli-dependent effect. | Neurochemical research 20091101 |
| Local salsolinol modulates dopamine extracellular levels from rat nucleus accumbens: shell/core differences. | Neurochemistry international 20090901 |
| Ferritin enhances salsolinol-mediated DNA strand breakage: protection by carnosine and related compounds. | Toxicology letters 20090710 |
| Fast liquid chromatography separation and multiple-reaction monitoring mass spectrometric detection of neurotransmitters. | Journal of separation science 20090701 |
| Characteristics of prolactin-releasing response to salsolinol (SAL) and thyrotropin-releasing hormone (TRH) in ruminants. | Domestic animal endocrinology 20090201 |
| Quantification of salsolinol enantiomers by stable isotope dilution liquid chromatography with tandem mass spectrometric detection. | Rapid communications in mass spectrometry : RCM 20081201 |
| The formation of catechol isoquinolines in PC12 cells exposed to manganese. | Neuroscience letters 20081024 |
| Identification of salsolinol in the mediobasal hypothalamus of lactating ewes and its relation to suckling-induced prolactin and GH release. | The Journal of endocrinology 20080701 |
| Salsolinol, an endogenous neurotoxin, enhances platelet aggregation and thrombus formation. | Thrombosis and haemostasis 20080701 |
| Iron contributes to the formation of catechol isoquinolines and oxidative toxicity induced by overdose dopamine in dopaminergic SH-SY5Y cells. | Neuroscience bulletin 20080601 |
| Interaction between salsolinol (SAL) and thyrotropin-releasing hormone (TRH) or dopamine (DA) on the secretion of prolactin in ruminants. | Domestic animal endocrinology 20080401 |
| Effect of (R)-salsolinol and N-methyl-(R)-salsolinol on the balance impairment between dopamine and acetylcholine in rat brain: involvement in pathogenesis of Parkinson disease. | Clinical chemistry 20080401 |
| Quantitative chiral analysis of salsolinol in different brain regions of rats genetically predisposed to alcoholism. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080301 |
| Salsolinol is present in the bovine posterior pituitary gland and stimulates the release of prolactin both in vivo and in vitro in ruminants. | Domestic animal endocrinology 20080201 |
| The reinforcing properties of salsolinol in the ventral tegmental area: evidence for regional heterogeneity and the involvement of serotonin and dopamine. | Alcoholism, clinical and experimental research 20080201 |
| The attenuating effect of memantine on staurosporine-, salsolinol- and doxorubicin-induced apoptosis in human neuroblastoma SH-SY5Y cells. | Neurochemistry international 20080101 |
| Simultaneous determination of salsolinol enantiomers and dopamine in human plasma and cerebrospinal fluid by chemical derivatization coupled to chiral liquid chromatography/electrospray ionization-tandem mass spectrometry. | Analytical chemistry 20071201 |
| The role of catecholamines in the prolactin release induced by salsolinol. | Neurochemistry international 20071001 |
| Salsolinol, a tetrahydroisoquinoline catechol neurotoxin, induces human Cu,Zn-superoxidie dismutase modificaiton. | Journal of biochemistry and molecular biology 20070930 |
| Antiapoptotic effects of nicotine in its protection against salsolinol-induced cytotoxicity. | Neurotoxicity research 20070701 |
| Salsolinol and the peripheral sympathetic activity: the effects of hypophysectomy, adrenalectomy and adrenal medullectomy. | Ideggyogyaszati szemle 20070330 |
| Effect of direct infusion of acetaldehyde on dopamine and dopamine-derived salsolinol in the striatum of free-moving rats using a reverse microdialysis technique. | Archives of toxicology 20070201 |
| The peripheral noradrenergic terminal as possible site of action of salsolinol as prolactoliberin. | Neurochemistry international 20070101 |
| TRPC1 protects human SH-SY5Y cells against salsolinol-induced cytotoxicity by inhibiting apoptosis. | Brain research 20060712 |
| Determination of salsolinol and related catecholamines through on-line preconcentration and liquid chromatography/atmospheric pressure photoionization mass spectrometry. | Analytical chemistry 20060515 |
| Salsolinol, a derivate of dopamine, is a possible modulator of catecholaminergic transmission: a review of recent developments. | Physiological research 20060101 |
| Chronic polysystemic candidiasis as a possible contributor to onset of idiopathic Parkinson's disease. | Bratislavske lekarske listy 20060101 |
| Neuroprotective effects of nicotine against salsolinol-induced cytotoxicity: implications for Parkinson's disease. | Neurotoxicity research 20051101 |
| Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics. | Alcoholism, clinical and experimental research 20050101 |
| Salsolinol, an antagonist of prolactoliberine, induces an increase in plasma catecholamine levels in the rat. | Autonomic neuroscience : basic & clinical 20040930 |
| Immobilization stress-induced increase in plasma catecholamine levels is inhibited by a prolactoliberin (salsolinol) administration. | Annals of the New York Academy of Sciences 20040601 |
| Pivotal role of an endogenous tetrahydroisoquinoline, salsolinol, in stress- and suckling-induced release of prolactin. | Annals of the New York Academy of Sciences 20040601 |
| Bioconversion studies in cultured cells of Corydalis species. | Die Pharmazie 20040601 |
| Salsolinol, a dopamine-derived tetrahydroisoquinoline, induces cell death by causing oxidative stress in dopaminergic SH-SY5Y cells, and the said effect is attenuated by metallothionein. | Brain research 20040416 |
| Increased systemic levels of norsalsolinol derivatives are induced by levodopa treatment and do not represent biological markers of Parkinson's disease. | Journal of neurology, neurosurgery, and psychiatry 20040401 |
| Liquid chromatography with amperometric detection at a nano crystalline Ce-doped lead dioxide film modified electrode for determination of (R)-Salsolinol, (R)-N-methylsalsolinol and monoamine neurotransmitters in Parkinsonian patients' cerebrospinal fluid. | The Analyst 20040301 |
| Stress- as well as suckling-induced prolactin release is blocked by a structural analogue of the putative hypophysiotrophic prolactin-releasing factor, salsolinol. | Journal of neuroendocrinology 20040301 |
| Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors: occurrence, metabolism and function in human brains. | Neurotoxicology 20040101 |
| Inhibition of DT-diaphorase potentiates the in vivo neurotoxic effect of intranigral injection of salsolinol in rats. | Neurotoxicity research 20040101 |
| [Change of dopamine, serotonin and opioid neuromediator systems in the brain of rats adapted to prolonged effect of ethanol]. | Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20040101 |
| Neuroprotective or neurotoxic activity of 1-methyl-1,2,3,4-tetrahydroisoquinoline and related compounds. | Bioorganic & medicinal chemistry letters 20030901 |
| In vivo study of salsolinol produced by a high concentration of acetaldehyde in the striatum and nucleus accumbens of free-moving rats. | Alcoholism, clinical and experimental research 20030801 |
| Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective. | Cellular and molecular biology (Noisy-le-Grand, France) 20030701 |
| Tyrosinase protects human melanocytes from ROS-generating compounds. | Biochemical and biophysical research communications 20030530 |
| Insulin-like growth factor-1 protects human dopaminergic SH-SY5Y cells from salsolinol-induced toxicity. | Neuroscience letters 20030410 |
| Salsolinol produces reinforcing effects in the nucleus accumbens shell of alcohol-preferring (P) rats. | Alcoholism, clinical and experimental research 20030301 |
| Effect of different doses of cyanamide on striatal salsolinol formation after ethanol treatment. | Legal medicine (Tokyo, Japan) 20030301 |
| Binding site of salsolinol: its properties in different regions of the brain and the pituitary gland of the rat. | Neurochemistry international 20030101 |
| ['Starburst' conjugates of proteins with carbocene polymers, carrying low molecular weight biologically-active compounds, and their immunogenicity]. | Bioorganicheskaia khimiia 20030101 |
| In vivo formation of salsolinol induced by high acetaldehyde concentration in rat striatum employing microdialysis. | Alcohol and alcoholism (Oxford, Oxfordshire) 20030101 |
| Axonal degeneration and progressive neurologic disability in multiple sclerosis. | Neurotoxicity research 20030101 |
| Salsolinol causing parkinsonism activates endoplasmic reticulum-stress signaling pathways in human dopaminergic SK-N-SH cells. | Neuro-Signals 20030101 |
| Assay of salsolinol in peripheral blood mononuclear cells of alcoholics and healthy subjects by gas chromatography-mass spectrometry. | Addiction biology 20021001 |
| Formation of novel toxic compounds from oxidative interaction between salsolinol and cysteine. | Journal of pharmaceutical and biomedical analysis 20020905 |
| Iron enhancement of oxidative DNA damage and neuronal cell death induced by salsolinol. | Journal of toxicology and environmental health. Part A 20020301 |
| Resistance of the insect cell line IPLB-LdFB to salsolinol-induced apoptosis. | Archives of insect biochemistry and physiology 20020101 |
| Physiological role of salsolinol: its hypophysiotrophic function in the regulation of pituitary prolactin secretion. | Neurotoxicology and teratology 20020101 |
| Salsolinol is a putative endogenous neuro-intermediate lobe prolactin-releasing factor. | Journal of neuroendocrinology 20011201 |
| Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents. | Bioorganic & medicinal chemistry 20011101 |
| Differential cell death induced by salsolinol with and without copper: possible role of reactive oxygen species. | Molecular pharmacology 20010901 |
| Oxidative DNA damage and cytotoxicity induced by copper-stimulated redox cycling of salsolinol, a neurotoxic tetrahydroisoquinoline alkaloid. | Free radical biology & medicine 20010615 |
| Possible role of salsolinol quinone methide in the decrease of RCSN-3 cell survival. | Biochemical and biophysical research communications 20010525 |
| Purification and characterization of coclaurine N-methyltransferase from cultured Coptis japonica cells. | Phytochemistry 20010401 |
| Salsolinol, a naturally occurring tetrahydroisoquinoline alkaloid, induces DNA damage and chromosomal aberrations in cultured Chinese hamster lung fibroblast cells. | Mutation research 20010301 |
| Biphasic effects of acetaldehyde-biogenic amine condensation products on membrane fluidity. | The Journal of pharmacy and pharmacology 20010101 |
| Opposite effect of simple tetrahydroisoquinolines on amphetamine- and morphine-stimulated locomotor activity in mice. | Journal of neural transmission (Vienna, Austria : 1996) 20010101 |
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