Tryptoline

Names

[ Name ]:
Tryptoline

[Synonym ]:
2,3,4,9-Tetrahydro-1H-β-carboline
Tetrahydro-b-carboline
Tetrahydro-β-carboline
1,2,3,4-Tetrahydro-b-carboline
2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-
MFCD00004954
1,2,3,4-Tetrahydro-9H-Pyrido[3,4-B]Indole
Tetrahydro-beta-carboline
Triptoline
Tryptoline

Biological Activity

[Description]:

Tetrahydro-β-carboline (Tryptoline) is a metabolite of tryptamine, also is a competitive serotonin reuptake inhibitor with an Ki value of 6.1 µM[1].

[Related Catalog]:

Research Areas >> Metabolic Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

serotonin:6.1 μM (Ki)

[In Vivo]

Tetrahydro-β-carboline (20 µg; i.c.v.) increases the serotonin levels in the same part of the brain in rats[1]. Animal Model: 180-200g female Sprague-Dawley rats[1] Dosage: 20 µg Administration: Intraventricular injection Result: Increased of serotonin levels in the same part of the brain whereas the monoamine oxidase activity was not altered.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
351.6±32.0 °C at 760 mmHg

[ Melting Point ]:
206-208 °C(lit.)

[ Molecular Formula ]:
C₁₁H₁₂N₂

[ Molecular Weight ]:
172.226

[ Flash Point ]:
166.5±25.1 °C

[ Exact Mass ]:
172.100052

[ PSA ]:
27.82000

[ LogP ]:
1.33

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.670

[ Storage condition ]:
Refrigerator

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Fingerprint analysis of thermolytic decarboxylation of tryptophan to tryptamine catalyzed by natural oils.

J. Chromatogr. A. 1210(1) , 115-20, (2008)

A number of N,N-dialkylated tryptamines show psychoactive properties in man which resulted in a renewed interest in psychopharmacological research. Attempts to manufacture these derivatives are increa...

Biosynthetic gene cluster for the cladoniamides, bis-indoles with a rearranged scaffold.

PLoS ONE 6(8) , e23694, (2011)

The cladoniamides are bis-indole alkaloids isolated from Streptomyces uncialis, a lichen-associated actinomycete strain. The cladoniamides have an unusual, indenotryptoline structure rarely observed a...

A class of oral N-[(1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]- N'-(amino-acid-acyl)hydrazine: discovery, synthesis, in vitro anti-platelet aggregation/in vivo anti-thrombotic evaluation and 3D QSAR analysis.

Eur. J. Med. Chem. 46 , 3237-49, (2011)

The in vivo anti-thrombotic activities of amino acid modified tetrahydro-β-carbolines depended upon the proximity of the side chain of the amino acid residue to the carboline-cycle. Based on this prox...