tryptoline

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| verifiedrevid = 470618432

| ImageFile = Tryptoline.svg

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| PIN = 2,3,4,9-Tetrahydro-1H-pyrido[3,4-b]indole

| OtherNames = Noreleagnine
Tetrahydronorharman
2,3,4,9-Tetrahydro-1H-β-carboline

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 96979

| 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

| InChIKey = CFTOTSJVQRFXOF-UHFFFAOYAW

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 269236

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CFTOTSJVQRFXOF-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 16502-01-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 65027TMI0H

| PubChem = 107838

| SMILES = c1ccc2c(c1)c3c([nH]2)CNCC3

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|Section2={{Chembox Properties

| Formula = C11H12N2

| MolarMass = 172.226 g/mol

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Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of β-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.{{cite web |title=Tryptoline |url=https://pubchem.ncbi.nlm.nih.gov/compound/107838 |website=pubchem.ncbi.nlm.nih.gov}}

Pharmacology

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.{{cite journal |last1=Youdim |first1=N.B.H. |last2=Oppenheim |first2=B. |title=The effect of tryptolines (1, 2, 3, 4-tetrahydro-β-carbolines) on monoamine metabolism and the platelet aggregation response in human platelets |journal=Neuroscience |date=April 1981 |volume=6 |issue=4 |pages=801–810 |doi=10.1016/0306-4522(81)90163-9 |pmid=7242917 |s2cid=37681465 |url=https://doi.org/10.1016/0306-4522(81)90163-9|url-access=subscription }}

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

In-vivo formation of tryptolines has been a matter of controversy.

See also

References