Tryptoline

Tryptoline
Names
	Preferred IUPAC name 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole
	Other names Noreleagnine; Tetrahydronorharman; 2,3,4,9-Tetrahydro-1H-β-carboline
Identifiers
CAS Number	16502-01-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL269236 ;
ChemSpider	96979 ;
ECHA InfoCard	100.156.194
PubChem CID	107838;
UNII	65027TMI0H ;
CompTox Dashboard (EPA)	DTXSID10167835 ;
	InChI InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Key: CFTOTSJVQRFXOF-UHFFFAOYSA-N ; InChI=1/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Key: CFTOTSJVQRFXOF-UHFFFAOYAW;
	SMILES c1ccc2c(c1)c3c([nH]2)CNCC3;
Properties
Chemical formula	C11H12N2
Molar mass	172.226 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of beta-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.^[1]

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Tryptolines are competitive selective inhibitors of the enzyme monoamine oxidase type A (MAO-A). 5-Hydroxytryptoline and 5-methoxytryptoline (pinoline) are the most active monoamine oxidase inhibitors (MAOIs) with IC₅₀s of 0.5 μM and 1.5 μM respectively.^[2]

Tryptolines are also potent reuptake inhibitors of serotonin and epinephrine, with a significantly greater selectivity for serotonin.^[2]

In vivo formation of tryptolines has been a matter of controversy.^[2]

[1]
"Tryptoline". pubchem.ncbi.nlm.nih.gov.
[2]
Youdim, N.B.H.; Oppenheim, B. (April 1981). "The effect of tryptolines (1, 2, 3, 4-tetrahydro-β-carbolines) on monoamine metabolism and the platelet aggregation response in human platelets". Neuroscience. 6 (4): 801–810. doi:10.1016/0306-4522(81)90163-9. PMID 7242917. S2CID 37681465.

[pubchem-1] [1]
"Tryptoline". pubchem.ncbi.nlm.nih.gov.

[NBH.Youdim1981-2] [2]
Youdim, N.B.H.; Oppenheim, B. (April 1981). "The effect of tryptolines (1, 2, 3, 4-tetrahydro-β-carbolines) on monoamine metabolism and the platelet aggregation response in human platelets". Neuroscience. 6 (4): 801–810. doi:10.1016/0306-4522(81)90163-9. PMID 7242917. S2CID 37681465.

[1]

[2]

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Tryptoline

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Pharmacology

See also

References

Names

Preferred IUPAC name 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole
Other names Noreleagnine Tetrahydronorharman 2,3,4,9-Tetrahydro-1H-β-carboline
Identifiers
CAS Number	16502-01-5^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL269236^Y
ChemSpider	96979^Y
ECHA InfoCard	100.156.194
PubChem CID	107838
UNII	65027TMI0H^Y
CompTox Dashboard (EPA)	DTXSID10167835
InChI InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2^Y Key: CFTOTSJVQRFXOF-UHFFFAOYSA-N^Y InChI=1/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2 Key: CFTOTSJVQRFXOF-UHFFFAOYAW
SMILES c1ccc2c(c1)c3c([nH]2)CNCC3
Properties
Chemical formula	C₁₁H₁₂N₂
Molar mass	172.226 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references