1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline profile

1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline, also known as **β-carboline-3-carboxylic acid trichloroethyl ester (β-CCT)**, is a compound that has garnered considerable attention in research due to its potential role in various physiological and pathological processes.

Here's why it's important:

**1. Potential Link to Alzheimer's Disease:**

* β-CCT is a potent inhibitor of the enzyme **acetylcholinesterase (AChE)**, which breaks down acetylcholine, a neurotransmitter essential for memory and cognition.
* AChE inhibitors are used as treatments for Alzheimer's disease.
* Researchers are exploring whether β-CCT could be a novel therapeutic agent for Alzheimer's, potentially offering better efficacy or fewer side effects compared to current treatments.

**2. Potential Role in Epilepsy:**

* β-CCT has been shown to possess anticonvulsant activity in animal models.
* It is proposed to exert this effect by modulating the activity of GABAergic neurons, which are involved in inhibiting neuronal activity and preventing seizures.
* More research is needed to confirm its potential therapeutic value for epilepsy.

**3. Possible Involvement in Drug Addiction:**

* β-CCT has been implicated in the development of addiction, particularly to opioids.
* It is thought to interact with the reward pathways in the brain, contributing to the addictive properties of these substances.
* Understanding the role of β-CCT in addiction could lead to new strategies for preventing or treating drug dependence.

**4. Other Potential Applications:**

* β-CCT has also been investigated for its potential applications in other areas, such as:
* **Antimicrobial activity:** It has shown activity against certain bacteria and fungi.
* **Anti-inflammatory effects:** Studies suggest it may possess anti-inflammatory properties.
* **Neuroprotective effects:** Research suggests it might protect neurons from damage in various neurological conditions.

**Important Note:**

* While β-CCT shows promise in research, it's crucial to remember that it is **not a clinically approved drug**.
* Further research is needed to determine its safety and efficacy for human use.

**In summary, β-CCT is a fascinating molecule with a wide range of potential applications. Its ability to modulate various biological processes makes it a subject of ongoing investigation in fields ranging from neurology and pharmacology to microbiology. The results of this research could ultimately lead to new and innovative therapies for a variety of diseases and conditions.**

1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	119183
SCHEMBL ID	8322885
MeSH ID	M0184673

Synonym
1-tcmtc
EC-000.2076
6649-90-7
rac 1-trichloromethyl-1,2,3,4-tetrahydro-\|a-carboline
(r)-taclo
131384-80-0
1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline
1-(trichloromethyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole
1-TRICHLOROMETHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE (TACLO)
1h-pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-1-(trichloromethyl)-, (+-)-
1-(trichloromethyl)-2,3,4,9-tetrahydro-1h-pyrido(3,4-b)indole
FT-0675455
SCHEMBL8322885
FT-0675456
FT-0675457
DTXSID70897166
rac 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline
rac 1-trichloromethyl-1,2,3,4-tetrahydro- beta -carboline hydrochloride salt
taclo hcl

Excerpt	Reference	Relevance
" Hence, the plasma levels of TaClo were determined at various time-points in 18 healthy volunteers in two periods each during a bioavailability study of several chloral hydrate preparations."	( [The plasma level of the neurotoxin 1-trichloromethyl-1,2,4,5-tetrahydro-beta-carboline (TaClo) in man after oral administration of chloral hydrate]. Beuscher, N; Jeromin, J; Leuschner, J; Ritter, H; Schulz, HU; Schürer, M; Zimmermann, T, 1998)	0.3
" [3-14C]-TaClo was poorly absorbed systemically, as indicated by the very low plasma radioactivity levels."	( Synthesis of radiolabelled 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline (TaClo), a neurotoxic chloral-derived mammalian alkaloid, and its biodistribution in rats. Bringmann, G; Brückner, R; Feineis, D; God, R; Grote, C; Wesemann, W, 2006)	0.63

Excerpt	Relevance	Reference
" Although it is not clear if the clinically administered dosage of chloral hydrate or the relatively high environmental levels of trichloroethylene could lead to an onset of Parkinson's disease, the spontaneous in vivo formation of TaClo and its pro-apoptotic properties, as shown in this report, should be considered."	( 1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline-induced apoptosis in the human neuroblastoma cell line SK-N-SH. Akundi, RS; Bringmann, G; Clement, HW; Fiebich, BL; Hüll, M; Lieb, K; Macho, A; Muñoz, E, 2004)	1.77

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	12 (42.86)	18.2507
2000's	12 (42.86)	29.6817
2010's	4 (14.29)	24.3611
2020's	0 (0.00)	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	1 (3.45%)	5.53%
Reviews	3 (10.34%)	6.00%
Case Studies	1 (3.45%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (82.76%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
2,3-dihydroxybenzoic acid 2,3-dihydroxybenzoic acid: RN given refers to parent cpd. dihydroxybenzoic acid : Any member of the class of hydroxybenzoic acids carrying two phenolic hydroxy groups on the benzene ring and its derivatives.. 2,3-dihydroxybenzoic acid : A dihydroxybenzoic acid that is benzoic acid substituted by hydroxy groups at positions 2 and 3. It occurs naturally in Phyllanthus acidus and in the aquatic fern Salvinia molesta.	1.99	1	0	dihydroxybenzoic acid	human xenobiotic metabolite; plant metabolite
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	1.99	1	0	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
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.	3.79	3	0	catechols; dihydroxyphenylacetic acid	human metabolite
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.	1.99	1	0	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.	1.99	1	0	indole-3-acetic acids	drug metabolite; human metabolite; mouse metabolite
chloral hydrate [no description available]	4.08	3	1	aldehyde hydrate; ethanediol; organochlorine compound	general anaesthetic; mouse metabolite; sedative; xenobiotic
oxidopamine Oxidopamine: A neurotransmitter analogue that depletes noradrenergic stores in nerve endings and induces a reduction of dopamine levels in the brain. Its mechanism of action is related to the production of cytolytic free-radicals.. oxidopamine : A benzenetriol that is phenethylamine in which the hydrogens at positions 2, 4, and 5 on the phenyl ring are replaced by hydroxy groups. It occurs naturally in human urine, but is also produced as a metabolite of the drug DOPA (used for the treatment of Parkinson's disease).	1.99	1	0	benzenetriol; catecholamine; primary amino compound	drug metabolite; human metabolite; neurotoxin
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	1.99	1	0	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
apomorphine Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.	1.98	1	0	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
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	2.4	2	0	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
trichloroacetaldehyde trichloroacetaldehyde : An organochlorine compound that consists of acetaldehyde where all the methyl hydrogens are replaced by chloro groups.	2.01	1	0	aldehyde; organochlorine compound	mouse metabolite
trichloroethylene Trichloroethylene: A highly volatile inhalation anesthetic used mainly in short surgical procedures where light anesthesia with good analgesia is required. It is also used as an industrial solvent. Prolonged exposure to high concentrations of the vapor can lead to cardiotoxicity and neurological impairment.. triol : A chemical compound containing three hydroxy groups.	2.01	1	0	chloroethenes	inhalation anaesthetic; mouse metabolite
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	2.07	1	0	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.07	1	0	xanthene
resazurin resazurin: used as indicator in detection of hyposulfite (sulfoxylate); in food research (reductase test); structure	2.07	1	0	phenoxazine
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.	1.99	1	0	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.39	2	0	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
hydroxyl radical Hydroxyl Radical: The univalent radical OH. Hydroxyl radical is a potent oxidizing agent.	6.99	1	0	oxygen hydride; oxygen radical; reactive oxygen species
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	2.07	1	0	amidobenzoic acid
cytochrome c-t Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.	2.93	1	0

Condition	Relationship Strength	Studies
Disease Exacerbation [description not available]	2.15	1
Idiopathic Parkinson Disease [description not available]	4.04	5
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	3.88	4
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)	4.04	5
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.21	1
Innate Inflammatory Response [description not available]	2.21	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.21	1
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.15	1
Autosomal Dominant Juvenile Parkinson Disease [description not available]	2.01	1
Parkinsonian Disorders A group of disorders which feature impaired motor control characterized by bradykinesia, MUSCLE RIGIDITY; TREMOR; and postural instability. Parkinsonian diseases are generally divided into primary parkinsonism (see PARKINSON DISEASE), secondary parkinsonism (see PARKINSON DISEASE, SECONDARY) and inherited forms. These conditions are associated with dysfunction of dopaminergic or closely related motor integration neuronal pathways in the BASAL GANGLIA.	2.01	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.4	2
Atherosclerotic Parkinsonism [description not available]	1.98	1
Parkinson Disease, Secondary Conditions which feature clinical manifestations resembling primary Parkinson disease that are caused by a known or suspected condition. Examples include parkinsonism caused by vascular injury, drugs, trauma, toxin exposure, neoplasms, infections and degenerative or hereditary conditions. Clinical features may include bradykinesia, rigidity, parkinsonian gait, and masked facies. In general, tremor is less prominent in secondary parkinsonism than in the primary form. (From Joynt, Clinical Neurology, 1998, Ch38, pp39-42)	1.98	1

1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline

Description

Cross-References

Synonyms (19)

Research Excerpts

Bioavailability

Dosage Studied

Research

Studies (28)

Market Indicators

Research Demand Index: 10.87

Study Types