Page last updated: 2024-12-08

1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid, (s)-isomer

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

## 1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid, (S)-isomer: An intriguing molecule

**1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acid (THβC) is a heterocyclic compound with a complex structure, known to exist in two isomeric forms: (S)-THβC and (R)-THβC.** The (S)-isomer is the focus of this discussion.

**Importance in Research:**

(S)-THβC has attracted significant research interest for its potential roles in:

**1. Neurological and Psychiatric Disorders:**

* **Alzheimer's disease:** Studies suggest (S)-THβC might act as a neuroprotective agent against amyloid-β toxicity, a key player in Alzheimer's.
* **Parkinson's disease:** Some research points to its potential to protect dopaminergic neurons, which are vulnerable in Parkinson's disease.
* **Depression:** (S)-THβC might act as a selective serotonin reuptake inhibitor (SSRI), similar to common antidepressant medications.
* **Anxiety:** Preliminary evidence suggests potential anxiolytic effects of (S)-THβC.

**2. Chemical Biology and Medicinal Chemistry:**

* **Drug development:** Its unique structure and biological activity make (S)-THβC an interesting starting point for designing novel drugs.
* **Understanding biological processes:** Investigating (S)-THβC can contribute to a better understanding of the complex interplay between neurotransmitters and receptors.

**3. Food Chemistry and Toxicology:**

* **Food safety:** (S)-THβC is a byproduct of the Maillard reaction, a crucial process in food browning and flavor development.
* **Potential toxicity:** Understanding its formation and potential toxicity in foods is crucial for ensuring food safety.

**However, it's crucial to note that research on (S)-THβC is still in its early stages:**

* **Limited clinical data:** Most of the evidence comes from in vitro and animal studies. More research is needed to understand its efficacy and safety in humans.
* **Potential side effects:** Its precise mechanism of action and potential side effects are not fully understood.

**Overall, 1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, (S)-isomer, holds promise as a potential therapeutic agent and a tool for understanding complex biological processes. However, extensive research is needed to translate its potential into real-world applications and ensure its safety for human use.**

lycoperodine-1: from Cirsium setosum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID449440
CHEMBL ID155546
SCHEMBL ID416557
MeSH IDM0323553

Synonyms (34)

Synonym
(s)-(-)-2,3,4,9-tetrahydro-1h-pyrido(3,4-b)indole-3-carboxylic
BIDD:GT0550
cyclomethyltryptophan
42438-90-4
l-1,2,3,4-tetrahydronorharman-3-carboxylic acid
CHEMBL155546
(3s)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole-3-carboxylic acid
AKOS004907297
(3s)-1h,2h,3h,4h,9h-pyrido[3,4-b]indole-3-carboxylic acid
(s)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole-3-carboxylic acid
A15567
AKOS015856022
SCHEMBL416557
l-1,2,3,4-tetrahydronorharmane-3-carboxylic acid
(3s)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
(3s)-1,2,3,4-tetrahydro-9h-pyrido[3,4-b]indole-3-carboxylic acid
FSNCEEGOMTYXKY-JTQLQIEISA-N
AC-25326
mfcd00272641
(-)-(3s)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
tnca, >=98% (hplc)
3s_2349_tetrahydro_1h_pyrido_34b_indole_carboxylic_acid
(3s)-2,3,4,9-tetrahydro-1h-beta-carboline-3-carboxylic acid
h-tpi-oh;l-1,2,3,4-tetrahydro--carboline-3-carboxylic acid;l-tryptoline-3-carboxylic acid;l-1,2,3,4-tetrahydro-9h-pyrido[3,4-b]indole-3-carboxylic acid
h-tpi-oh
Q27466042
PS-12531
DTXSID40962491
lycoperodine-1
(s)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole-3-carboxylicacid
CS-0082781
EN300-312396
(s)-1,2,3,4-tetrahydronorharmane-3-carboxylic acid
Z1508915935
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID388927Inhibition of platelet-activating factor-induced platelet aggregation in pig blood2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
(3S)-N-(L-Aminoacyl)-1,2,3,4-tetrahydroisoquinolines, a class of novel antithrombotic agents: synthesis, bioassay, 3D QSAR, and ADME analysis.
AID473123Antiplatelet aggregation activity against arachidonic acid-induced pig platelet aggregation after 5 mins by aggregometer2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
A class of 3S-2-aminoacyltetrahydro-beta-carboline-3-carboxylic acids: their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency.
AID473125Antiplatelet aggregation activity against thrombin-induced pig platelet aggregation after 5 mins by aggregometer2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
A class of 3S-2-aminoacyltetrahydro-beta-carboline-3-carboxylic acids: their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency.
AID165509Tested in vitro for maximal rate of platelet aggregation induced by adenosine diphosphate (10 e5 mol/L) at a dose of 10 e6 mol/L in rabbit blood2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID630252Inhibition of TNF-alpha-induced NFkappaB activation in human HEK293 cells at 50 uM after 6 hrs by luciferase assay relative to control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
AID190471Tested for the effect on the dry thrombus weight at a dose of 5 uM/kg in male wistar anesthetized rat2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID473131Antithrombotic activity in Wistar rat arterioveinos cannula model assessed as reduction of thrombus weight at 5 umol/kg, iv2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
A class of 3S-2-aminoacyltetrahydro-beta-carboline-3-carboxylic acids: their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency.
AID388925Inhibition of adenosine diphosphate-induced platelet aggregation in pig blood2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
(3S)-N-(L-Aminoacyl)-1,2,3,4-tetrahydroisoquinolines, a class of novel antithrombotic agents: synthesis, bioassay, 3D QSAR, and ADME analysis.
AID200412Tested for the effect of compound on the adhesion of high pulmonary metastatic SACC cell line SACC-LM and platelets at 5 mg/mL2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID388926Inhibition of arachidonic acid-induced platelet aggregation in pig blood2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
(3S)-N-(L-Aminoacyl)-1,2,3,4-tetrahydroisoquinolines, a class of novel antithrombotic agents: synthesis, bioassay, 3D QSAR, and ADME analysis.
AID630247Inhibition of aromatase at 50 uM after 10 mins preincubation by plate reader relative to control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
AID165508Tested in vitro for maximal rate of platelet aggregation induced by adenosine diphosphate (10 e5 mol/L) at a dose of 10 e5 mol/L in rabbit blood2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID630244Induction of quinone reductase 1 activity in mouse Hepa-1c1c7 cells at 50 uM by MTT assay relative to untreated control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
AID165512Tested in vitro for the maximal rate of platelet aggregation induced by platelet activating factor (10 e-7 mol/L) at a dose of 10 e6 mol/L in rabbit blood2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID388928Inhibition of thrombin-induced platelet aggregation in pig blood2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
(3S)-N-(L-Aminoacyl)-1,2,3,4-tetrahydroisoquinolines, a class of novel antithrombotic agents: synthesis, bioassay, 3D QSAR, and ADME analysis.
AID165513Tested in vitro for the maximal rate of platelet aggregation induced by platelet activating factor (10 e-7 mol/L) at a dose of 10 e7 mol/L in rabbit blood2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID165511Tested in vitro for the maximal rate of platelet aggregation induced by platelet activating factor (10 e-7 mol/L) at a dose of 10 e5 mol/L in rabbit blood2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID630249Inhibition of iNOS-mediated nitric oxide production in LPS-stimulated mouse RAW 264.7 cells at 50 uM pretreated 15 mins before LPS challenge measured after 20 hrs relative to control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
AID165510Tested in vitro for maximal rate of platelet aggregation induced by adenosine diphosphate (10 e5 mol/L) at a dose of 10 e7 mol/L in rabbit blood2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID190475Tested for the effect on the wet thrombus weight at a dose of 5 umol/kg in male wistar anesthetized rat2002Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4
Synthesis and antithrombotic activity of carbolinecarboxyl RGD sequence.
AID630250Inhibition of iNOS-mediated nitric oxide production in LPS-stimulated mouse RAW 264.7 cells assessed as cell survival at 50 uM pretreated 15 mins before LPS challenge measured after 20 hrs relative to control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
AID630253Inhibition of TNF-alpha-induced NFkappaB activation in human HEK293 cells assessed as cell survival at 50 uM after 6 hrs by luciferase assay relative to control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
AID473122Antiplatelet aggregation activity against platelet-activating factor-induced pig platelet aggregation after 5 mins by aggregometer2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
A class of 3S-2-aminoacyltetrahydro-beta-carboline-3-carboxylic acids: their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency.
AID473124Antiplatelet aggregation activity against ADP-induced pig platelet aggregation after 5 mins by aggregometer2010Journal of medicinal chemistry, Apr-22, Volume: 53, Issue:8
A class of 3S-2-aminoacyltetrahydro-beta-carboline-3-carboxylic acids: their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency.
AID1167629Antioxidant activity assessed as ratio of trolox equivalents of ABTS radical scavenging activity after 6 mins2014Bioorganic & medicinal chemistry, Nov-01, Volume: 22, Issue:21
Design, synthesis and evaluation of novel tacrine-(β-carboline) hybrids as multifunctional agents for the treatment of Alzheimer's disease.
AID630245Induction of quinone reductase 1 activity in mouse Hepa-1c1c7 cells assessed as cell survival at 50 uM by MTT assay relative to control2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis, and biological evaluation of callophycin A and analogues as potential chemopreventive and anticancer agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's4 (66.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.43

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.43 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]