Classification Term: 972

Tetrahydroisoquinolines (ontology term: CHEMONTID:0002955)

Tetrahydrogenated isoquinoline derivatives." []

found 45 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Organoheterocyclic compounds

Child Taxonomies: 1-phenethyltetrahydroisoquinolines, 1-phenyltetrahydroisoquinolines, 4-phenyltetrahydroisoquinolines

Etoposide

(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

C29H32O13 (588.1842822)


Etoposide is a beta-D-glucoside, a furonaphthodioxole and an organic heterotetracyclic compound. It has a role as an antineoplastic agent and a DNA synthesis inhibitor. It is functionally related to a podophyllotoxin and a 4-demethylepipodophyllotoxin. A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. Etoposide is a Topoisomerase Inhibitor. The mechanism of action of etoposide is as a Topoisomerase Inhibitor. Etoposide is a natural product found in Aspergillus porosus, Aspergillus alliaceus, and other organisms with data available. Etoposide is a semisynthetic derivative of podophyllotoxin, a substance extracted from the mandrake root Podophyllum peltatum. Possessing potent antineoplastic properties, etoposide binds to and inhibits topoisomerase II and its function in ligating cleaved DNA molecules, resulting in the accumulation of single- or double-strand DNA breaks, the inhibition of DNA replication and transcription, and apoptotic cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. (NCI04) A semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. A semisynthetic derivative of PODOPHYLLOTOXIN that exhibits antitumor activity. Etoposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA. This complex induces breaks in double stranded DNA and prevents repair by topoisomerase II binding. Accumulated breaks in DNA prevent entry into the mitotic phase of cell division, and lead to cell death. Etoposide acts primarily in the G2 and S phases of the cell cycle. See also: Etoposide Phosphate (active moiety of). Etoposide, also known as vepesid or VP-16, belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Etoposide is a drug. Within humans, etoposide participates in a number of enzymatic reactions. In particular, etoposide can be converted into etoposide ortho-quinone; which is mediated by the enzymes prostaglandin g/h synthase 1 and prostaglandin g/h synthase 2. In addition, etoposide and uridine diphosphate glucuronic acid can be converted into etoposide glucuronide and uridine 5-diphosphate; which is mediated by the enzyme UDP-glucuronosyltransferase 1-1. In humans, etoposide is involved in etoposide metabolism pathway. Etoposide is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Etoposide is used as a form of chemotherapy for cancers such as Kaposis sarcoma, Ewings sarcoma, lung cancer, testicular cancer, lymphoma, nonlymphocytic leukemia, and glioblastoma multiforme. It is given intravenously (IV) or orally in capsule or tablet form. It is believed to work by damaging DNA. Etoposide was approved for medical use in the United States in 1983. They can include low blood cell counts, vomiting, loss of appetite, diarrhea, hair loss, and fever. L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01C - Plant alkaloids and other natural products > L01CB - Podophyllotoxin derivatives C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product > C1331 - Epipodophyllotoxin Compound C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials C1907 - Drug, Natural Product D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Raw Data] CB195_Etoposide_pos_20eV_CB000069.txt [Raw Data] CB195_Etoposide_pos_50eV_CB000069.txt [Raw Data] CB195_Etoposide_pos_10eV_CB000069.txt [Raw Data] CB195_Etoposide_pos_40eV_CB000069.txt [Raw Data] CB195_Etoposide_pos_30eV_CB000069.txt Etoposide (VP-16; VP-16-213) is an anti-cancer chemotherapy agent. Etoposide inhibits topoisomerase II, thus stopping DNA replication. Etoposide induces cell cycle arrest, apoptosis and autophagy[1]. Etoposide (VP-16; VP-16-213) is an anti-cancer chemotherapy agent. Etoposide inhibits topoisomerase II, thus stopping DNA replication. Etoposide induces cell cycle arrest, apoptosis and autophagy[1].

   

Debrisoquine

1,2,3,4-tetrahydroisoquinoline-2-carboximidamide

C10H13N3 (175.1109418)


Debrisoquine is an adrenergic neuron-blocking drug. Genetic and environmental factors are determinants of the interindividual and interethnic variability in drug metabolism. Thus, interethnic differences in debrisoquine hydroxylation polymorphism (Cytochrome p450, subfamily IID, polypeptide 6, CYP2D6) might be partly responsible for the variation in haloperidol disposition between races. The influence of tobacco, ethanol, caffeine, gender, and oral contraceptive use on the debrisoquine metabolic ratio (MR) has been analyzed in panels of healthy volunteers. About 5-10\\% of European white population has a genetically determinant defect of the CYP2D6, one of the enzymes of cytochrome P-450. This defect leads to the impaired metabolism of many drugs including various psychopharmacological agents. The measurement of the hydroxylation of debrisoquine is a laboratory test which allows identifying such an individual. Patients who show an impaired hydroxylation of debrisoquine usually demonstrate severe side effects and poor outcome of psychopharmacotherapy. In practice, knowledge of a patients debrisoquine metabolic phenotype is an advantage when prescribing tricyclic antidepressants and neuroleptics, as the drug concentration will be considerably higher in slow metabolisers than in the average patient. (PMID: 8839686, 1738265, 7878155) [HMDB] Debrisoquine is an adrenergic neuron-blocking drug. Genetic and environmental factors are determinants of the interindividual and interethnic variability in drug metabolism. Thus, interethnic differences in debrisoquine hydroxylation polymorphism (Cytochrome p450, subfamily IID, polypeptide 6, CYP2D6) might be partly responsible for the variation in haloperidol disposition between races. The influence of tobacco, ethanol, caffeine, gender, and oral contraceptive use on the debrisoquine metabolic ratio (MR) has been analyzed in panels of healthy volunteers. About 5-10\\% of European white population has a genetically determinant defect of the CYP2D6, one of the enzymes of cytochrome P-450. This defect leads to the impaired metabolism of many drugs including various psychopharmacological agents. The measurement of the hydroxylation of debrisoquine is a laboratory test which allows identifying such an individual. Patients who show an impaired hydroxylation of debrisoquine usually demonstrate severe side effects and poor outcome of psychopharmacotherapy. In practice, knowledge of a patients debrisoquine metabolic phenotype is an advantage when prescribing tricyclic antidepressants and neuroleptics, as the drug concentration will be considerably higher in slow metabolisers than in the average patient. (PMID: 8839686, 1738265, 7878155). C - Cardiovascular system > C02 - Antihypertensives > C02C - Antiadrenergic agents, peripherally acting > C02CC - Guanidine derivatives C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013565 - Sympatholytics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents COVID info from COVID-19 Disease Map ATC code: C02CC04 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Salsolinol

1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

C10H13NO2 (179.09462380000002)


(r)-salsolinol, also known as salsolinol, (+-)-isomer or 1-methyl-6,7-dihydroxytetrahydroisoquinoline, is a member of the class of compounds known as tetrahydroisoquinolines. Tetrahydroisoquinolines are tetrahydrogenated isoquinoline derivatives (r)-salsolinol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (r)-salsolinol can be found in cocoa and cocoa products and fruits, which makes (r)-salsolinol a potential biomarker for the consumption of these food products (r)-salsolinol can be found primarily in blood, cerebrospinal fluid (CSF), and feces. Moreover, (r)-salsolinol is found to be associated with hypertension, multiple system atrophy, and parkinsons disease. Salsolinol belongs to the family of Isoquinolines. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine. Salsolinol is a biomarker for the consumption of bananas.

   

Praziquantel

2-cyclohexanecarbonyl-1H,2H,3H,4H,6H,7H,11bH-piperazino[2,1-a]isoquinolin-4-one

C19H24N2O2 (312.18376839999996)


Praziquantel is only found in individuals that have used or taken this drug. It is an anthelmintic used in most schistosome and many cestode infestations. [PubChem]Praziquantel works by causing severe spasms and paralysis of the worms muscles. This paralysis is accompanied - and probably caused - by a rapid Ca 2+ influx inside the schistosome. Morphological alterations are another early effect of praziquantel. These morphological alterations are accompanied by an increased exposure of schistosome antigens at the parasite surface. The worms are then either completely destroyed in the intestine or passed in the stool. An interesting quirk of praziquantel is that it is relatively ineffective against juvenile schistosomes. While initially effective, effectiveness against schistosomes decreases until it reaches a minimum at 3-4 weeks. Effectiveness then increases again until it is once again fully effective at 6-7 weeks. Glutathione S-transferase (GST), an essential detoxification enzyme in parasitic helminths, is a major vaccine target and a drug target against schistosomiasis. Schistosome calcium ion channels are currently the only known target of praziquantel. P - Antiparasitic products, insecticides and repellents > P02 - Anthelmintics > P02B - Antitrematodals > P02BA - Quinoline derivatives and related substances D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C250 - Antihelminthic Agent

   

(-)-Salsoline

1(R),2(N)-Dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

C11H15NO2 (193.110273)


(-)-Salsoline is a compound that crystallizes from alcohol solution, melts at 221 oC, soluble in hot alcohol and chloroform; used in medicine as an antihypertensive agent. Salsoline as well as salsolinol were found in male alcoholic inpatientss urine and lumbar cerebrospinal fluid when patients were still intoxicated after a heavy alcohol debauch and after they had been inpatients and off alcohol for one week.There was a wide interindividual variation and no statistical significant difference in the levels between the first and second sampling in CSF or urine.[PMID: 6935920]. (-)-Salsoline is a compound that crystallizes from alcohol solution, melts at 221 oC, soluble in hot alcohol and chloroform; used in medicine as an antihypertensive agent. D009676 - Noxae > D009498 - Neurotoxins

   

Tetrabenazine

9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

C19H27NO3 (317.1990832)


A drug formerly used as an antipsychotic but now used primarily in the treatment of various movement disorders including tardive dyskinesia. Tetrabenazine blocks uptake into adrenergic storage vesicles and has been used as a high affinity label for the vesicle transport system. [PubChem] D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators N - Nervous system Same as: D08575

   

(R)-Salsolinol

1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

C10H13NO2 (179.09462380000002)


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). Alkaloid from Annona reticulata (custard apple), Musa paradisiaca (banana) and Theobroma cacao (cocoa). xi-Salsolinol is found in cocoa and cocoa products and fruits.

   

Hydrocotarnine

1,2,3,4-tetrahydro-8-Methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinoline, 9ci

C12H15NO3 (221.105188)


Hydrocotarnine is an alkaloid from opium (Papaver somniferum). Alkaloid from opium (Papaver somniferum). Hydrocotarnine is a Cbl inhibitor, and results in inflammasome-mediated IL-18 secretion in colitis. Hydrocotarnine increases expression of GLUT1 and cellular glucose uptake in glycolytic metabolism. Hydrocotarnine acts as an agent that provides analgesic effect in cancer research[1][2][3].

   

O-Methylcorypalline

1,2,3,4-tetrahydro-6,7-Dimethoxy-2-methyl-isoquinoline

C12H17NO2 (207.12592220000002)


O-Methylcorypalline is found in coffee and coffee products. O-Methylcorypalline is an alkaloid from Nelumbo nucifera (East Indian lotus Alkaloid from Nelumbo nucifera (East Indian lotus). O-Methylcorypalline is found in tea, coffee and coffee products, and sacred lotus.

   

Norsalsolinol

6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline

C9H11NO2 (165.0789746)


Norsalsolinol is a putative metabolic neuromodulators that hs been found to be present in both rat and human brains. It modulates dopaminergic transmission and have been shown to be associated with neurotoxicity within cells and diseases such as alcoholism and Parkinsonism. Norsalsolinol can be synthesized in vivo non-enzymatically by condensation of dopamine with formaldehyde, the oxidized metabolite of methanol. A human metabolite taken as a putative food compound of mammalian origin [HMDB]

   

2(N)-Methyl-norsalsolinol

2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

C10H13NO2 (179.09462380000002)


2(N)-methyl-norsalsolinol (NMNorsal) is a dihydroxylated tetrahydroisoquinoline derivative 2(N)-analogue of salsolinol, identified as a putative endogenous neurotoxin in patients with Parkinsons disease. A prominent blood-brain barrier (BBB) is described to exist for salsolinol, but penetration of NMNorsal occurs through the BBB into the caudate nucleus of the rat brain. There was no alteration in extracellular dopamine or 3,4-dihydroxyphenylacetic acid levels. (PMID 11924888). 2(N)-methyl-norsalsolinol was identified in L-DOPA-treated patients with Parkinsons disease and proposed to be responsible for behavioral changes. Atypical heterocyclic L-DOPA/dopamine metabolite NMNorsal is able to modify long-term regulation of serotonin and opioid receptor expression in striatum. Since the occurrence of hallucinosis or psychosis following L-DOPA treatment is related to the serotonergic system, these results probably reflect a link between NMNorsal and L-DOPA side effects in Parkinsons disease. (PMID 14607311). 2(N)-methyl-norsalsolinol (NMNorsal) is a dihydroxylated tetrahydroisoquinoline derivative 2(N)-analogue of salsolinol, identified as a putative endogenous neurotoxin in patients with Parkinsons disease. A prominent blood-brain barrier (BBB) is described to exist for salsolinol, but penetration of NMNorsal occurs through the BBB into the caudate nucleus of the rat brain. There was no alteration in extracellular dopamine or 3,4-dihydroxyphenylacetic acid levels. (PMID 11924888)

   

1,2,3,4-Tetrahydroisoquinoline

HCL OF 1,2,3,4-Tetrahydroisoquinoline

C9H11N (133.0891446)


Tetrahydroisoquinoline is a secondary amine with the chemical formula C9H11N.Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.The tetrahydroisoquinoline skeleton is commonly encountered in pharmaceutical drugs, notably quaternary ammonium muscle relaxants. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This theory has now been discredited and is no longer generally accepted by the scientific community, but endogenous production of neurotoxic tetrahydroisoquinoline derivatives such as norsalsolinol continue to be investigated as possible causes for some conditions such as Parkinsons disease.{from wiki) [HMDB] Tetrahydroisoquinoline is a secondary amine with the chemical formula C9H11N.Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide.The tetrahydroisoquinoline skeleton is commonly encountered in pharmaceutical drugs, notably quaternary ammonium muscle relaxants. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This theory has now been discredited and is no longer generally accepted by the scientific community, but endogenous production of neurotoxic tetrahydroisoquinoline derivatives such as norsalsolinol continue to be investigated as possible causes for some conditions such as Parkinsons disease.{from wiki).

   

Litcubine

4,13-dihydroxy-5,14-dimethoxy-10-methyl-10-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11,13,15-hexaen-10-ium

C19H22NO4+ (328.15487520000005)


Litcubine is found in fruits. Litcubine is an alkaloid from the roots of Litsea cubeba (mountain pepper

   

Litcubinine

2,9,10-trihydroxy-3-methoxy-7-methyl-5H,6H,7H,12H,12aH-indolo[2,1-a]isoquinolin-7-ium

C18H20NO4+ (314.139226)


Litcubinine is found in fruits. Litcubinine is an alkaloid from the roots of Litsea cubeba (mountain pepper

   

(R)-N-Methylsalsolinol

1(R),2(N)-Dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

C11H15NO2 (193.110273)


1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [N-methyl-(R)salsolinol, NM(R)Sal] is the most potent toxin among isoquinolines. Endogenous isoquinolines with and without catechol structure have been proposed to be neurotoxins specific for dopamine neurons. (PMID 9085193). (R)salsolinol N-methyltransferase synthesizes N-methyl(R)salsolinol, which is further oxidized into 1,2-dimethyl-6,7-dihydroxyisoquinolinium ion by non-enzymatic and enzymatic oxidation. (PMID 14697894). Dopamine-derived N-methyl(R)salsolinol is an endogenous MPTP-like neurotoxin to cause Parkinsons disease. In the cerebrospinal fluid from newly diagnosed untreated patients with Parkinsons disease, the level of this toxin was found to increase significantly, compared to control and a disease control, multiple system atrophy. L-DOPA therapy did not seem to affect the level of this toxin. The results suggest that N-methyl(R)salsolinol level in the cerebrospinal fluid may indicate remaining dopamine neurons in the parkinsonian brain. (PMID 10076861). N-methyl(R)salsolinol (NM(R)Sal) induces apoptosis (but not necrosis) in SH-SY5Y cells, and the apoptotic cascade is initiated by mitochondrial permeability transition and activated by stepwise reactions. (PMID 12200198). 1(R),2(N)-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline [N-methyl-(R)salsolinol, NM(R)Sal] is the most potent toxin among isoquinolines. Endogenous isoquinolines with and without catechol structure have been proposed to be neurotoxins specific for dopamine neurons. (PMID 9085193) D009676 - Noxae > D009498 - Neurotoxins

   

(S)-N-Methylsalsolinol

HBR(S)-Isomer OF 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline

C11H15NO2 (193.110273)


1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline is an endogenous amine in parkinsonian and normal human brain. (PMID 2049084). Endogenous isoquinolines with and without catechol structure have been proposed to be neurotoxins specific for dopamine neurons. (PMID 9085193). 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline is an endogenous amine in parkinsonian and normal human brain. (PMID 2049084)

   

4-Hydroxydebrisoquine

4-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide

C10H13N3O (191.1058568)


Debrisoquine is metabolized to 4-hydroxydebrisoquine by CYP2D6. Due to this, it has been used widely to determine the hydroxylation capacity of the enzyme.(PMID:15843230) [HMDB] Debrisoquine is metabolized to 4-hydroxydebrisoquine by CYP2D6. Due to this, it has been used widely to determine the hydroxylation capacity of the enzyme.(PMID:15843230).

   

(R)-1,2-dimethyl-5,6-dihydroxy-tetrahydroisoquinoline

(1R)-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline-5,6-diol

C11H15NO2 (193.110273)


This compound is a derivative of Tetrahydroisoquinoline, which is involved in the Tyrosine metabolism as a reaction product of S-adenosyl L-methionine with salsolinol. Tetrahydroisoquinoline derivatives may be formed in the body as metabolites of some drugs, and this was once thought to be involved in the development of alcoholism.This theory has now been discredited and is no longer generally accepted by the scientific community, but endogenous production of neurotoxic tetrahydroisoquinoline derivatives such as norsalsolinol continue to be investigated as possible causes for some conditions such as Parkinsons disease. This compound is a derivative of Tetrahydroisoquinoline, which is involved in the Tyrosine metabolism as a reaction product of S-adenosyl L-methionine with salsolinol

   

Salsoline-1-carboxylate

(1R)-6-hydroxy-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

C12H15NO4 (237.100103)


Salsoline-1-carboxylic acid is a intermidiate metabolite in the synthesis of Salsoline and it can be directly oxidized by certain enzyme. It can also be synthesized through another intermediate metabolite Salsolinol 1-carboxylate via Catechol O-methyltransferase. Salsoline-1-carboxylic acid is a intermidiate metabolite in the synthesis of Salsoline and it can be directly oxidized by certain enzyme

   

Salsolinol 1-carboxylate

(1S)-6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

C11H13NO4 (223.0844538)


Salsolinol-1-carboxylic acid is an intermediate metabolite formed during the synthesis with dopamine and pyruvate towards the endogenous neurotoxin, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (salsolinol),which has been considered a potential causative factor for Parkinsons disease (PD). Salsolinol-1-carboxylic acid can be directly metabolized by an unknown enzyme to salsolinol or at first to 1,2-dehydrosalsolinol and then to salsolinol. Salsolinol-1-carboxylic acid is an intermediate metabolite formed during the synthesis with dopamine and pyruvate towards the endogenous neurotoxin, 1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (salsolinol),which has been considered a potential causative factor for Parkinsons disease (PD)

   

Benzquinamide

2-(Acetyloxy)-N,N-diethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine-3-carboxamide

C22H32N2O5 (404.2311102)


Benzquinamide is only found in individuals that have used or taken this drug. It is an antiemetic compound with antihistaminic, mild anticholinergic, and sedative properties.The mechanism of action is not known, but presumably benzquinamide works via antagonism of muscarinic acetycholine receptors and histamine H1 receptors.

   

Drotaverine

(1Z)-1-[(3,4-diethoxyphenyl)methylidene]-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline

C24H31NO4 (397.22529660000004)


Drotaverine (INN, also known as drotaverin) is an antispasmodic drug, structurally related to papaverine. Drotaverine is a selective inhibitor of phosphodiesterase 4, and has no anticholinergic effects. Drotaverine has been shown to possess dose-dependant analgesic effects in animal models. One small study has shown drotaverine to be eliminated mainly non-renally. A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03A - Drugs for functional gastrointestinal disorders > A03AD - Papaverine and derivatives C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C29698 - Antispasmodic Agent D002491 - Central Nervous System Agents > D000700 - Analgesics D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents

   

N-methyl-4,6,7-trihydroxy-1,2,3,4-tetrahydroisoquinoline

1,2,3,4-Tetrahydro-2-methyl-4,6,7-isoquinolinetriol hydrochloride

C10H13NO3 (195.0895388)


This compound belongs to the family of Isoquinolines and Derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine

   

4,6,7-Trihydroxy-1,2,3,4-tetrahydroisoquinoline

4,6,7-Trihydroxy-1,2,3,4-tetrahydroisoquinoline

C9H11NO3 (181.0738896)


This compound belongs to the family of Isoquinolines and Derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine

   

b-Dihydrotetrabenazine

9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-ol

C19H29NO3 (319.2147324)


b-Dihydrotetrabenazine is a metabolite of tetrabenazine. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder and is marketed under the trade names Nitoman in Canada and Xenazine in New Zealand and some parts of Europe, and is also available in the USA as an orphan drug. On August 15, 2008 the U.S. Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntingtons disease (HD), the first in the US. The compound has been known since the 1950s. (Wikipedia)

   

alpha-dihydrotetrabenazine

(2R,3S)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-ol

C19H29NO3 (319.2147324)


alpha-dihydrotetrabenazine is a metabolite of tetrabenazine. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder and is marketed under the trade names Nitoman in Canada and Xenazine in New Zealand and some parts of Europe, and is also available in the USA as an orphan drug. On August 15, 2008 the U.S. Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntingtons disease (HD), the first in the US. The compound has been known since the 1950s. (Wikipedia)

   

(-)-N-(2-((R)-3-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)piperidino)ethyl)-4-fluorobenzamide

(-)-N-(2-((R)-3-(6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)piperidino)ethyl)-4-fluorobenzamide

C26H32FN3O4 (469.2376724)


   

Salsolinol-1-carboxylic acid

1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

C11H13NO4 (223.0844538)


   

1-Methyl-1,2,3,4-tetrahydroisoquinoline

N-Methyl-1,2,3,4-tetrahydroisoquinoline

C10H13N (147.1047938)


   

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, hydrochloride, (S)-isomer

C10H11NO2 (177.0789746)


   

1,2,3,4-Tetrahydroisoquinoline-7-sulfonamide

1,2,3,4-Tetrahydro-isoquinoline-7-sulphonic acid amide

C9H12N2O2S (212.0619452)


   

1-(1-Naphthylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

1-[(naphthalen-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

C20H19NO2 (305.14157140000003)


   

N-(4-Fluorophenyl)-4,5-dimethyl-6-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-YL]pyrimidin-2-amine

N-(4-Fluorophenyl)-4,5-dimethyl-6-[(1S)-1-methyl-3,4-dihydro-1H-isoquinolin-2-YL]pyrimidin-2-amine

C22H23FN4 (362.19066499999997)


C78276 - Agent Affecting Digestive System or Metabolism > C29701 - Anti-ulcer Agent

   

1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid

1,2,3,4-Tetrahydroisoquinoline-1-carboxylic acid

C10H11NO2 (177.0789746)


   

6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

6,7-DIMETHOXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID

C12H15NO4 (237.100103)


   

7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline

7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline

C9H9Cl2N (201.0112014)


   

8,9-Dihydroxy-1,5,6,10B-tetrahydropyrrolo[2,1-A]isoquinolin-3(2H)-one

8,9-Dihydroxy-1,5,6,10B-tetrahydropyrrolo[2,1-A]isoquinolin-3(2H)-one

C12H13NO3 (219.0895388)


   

Quinocarmycin analog

12-cyano-10-(hydroxymethyl)-8-methoxy-16-methyl-11,16-diazatetracyclo[11.2.1.0^{2,11}.0^{4,9}]hexadeca-4(9),5,7-triene-15-carboxylic acid

C19H23N3O4 (357.16884780000004)


D000970 - Antineoplastic Agents

   

Florbenazine

9-(3-fluoropropoxy)-10-methoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-ol

C21H32FNO3 (365.2366094)


   

2-[(3-Phenyl-5,6-dihydro-2h-1,2,4-oxadiazin-6-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

2-[(3-Phenyl-5,6-dihydro-2h-1,2,4-oxadiazin-6-yl)methyl]-1,2,3,4-tetrahydroisoquinoline

C19H21N3O (307.1684536)


   

2H-Benzo(a)quinolizin-2-ol, 2-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-3-(2-methylpropyl)-

2-ethyl-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-ol

C21H33NO3 (347.2460308000001)


   

1-(Naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

1-[(naphthalen-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

C20H19NO2 (305.14157140000003)


   

Methylsulfonyl 4-[(2-carbamimidoyl-3,4-dihydro-1H-isoquinolin-7-yl)oxymethyl]-1-pyridin-4-ylpiperidine-4-carboxylate

Methanesulphonyl 4-{[(2-carbamimidoyl-1,2,3,4-tetrahydroisoquinolin-7-yl)oxy]methyl}-1-(pyridin-4-yl)piperidine-4-carboxylic acid

C23H29N5O5S (487.18893040000006)


   

1,2,3,4-Tetrahydroisoquinolin-1-yl formate

1,2,3,4-Tetrahydroisoquinolin-1-yl formic acid

C10H11NO2 (177.0789746)


   

Soquinolol

5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde

C17H26N2O3 (306.19433260000005)


C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C72900 - Adrenergic Antagonist