N-Monoalkyltryptamines

Frovatriptan, sold under the brand name Frova among others, is a triptan medication developed by Vernalis for the treatment of migraine headaches and for short term prevention of menstrual migraine. The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.

Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a harmala alkaloid and β-carboline which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It is the partly hydrogenated form of harmine.

'''N-Methyltryptamine (NMT), also known as monomethyltryptamine''', is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

Panobinostat, sold under the brand name Farydak, is a medication used for the treatment of multiple myeloma. It is a hydroxamic acid and acts as a non-selective histone deacetylase inhibitor (pan-HDAC inhibitor).

Baeocystin, also known as norpsilocybin or '4-phosphoryloxy-N-methyltryptamine (4-PO-NMT'), is a zwitterionic alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms together with psilocybin, psilocin (4-HO-DMT), norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT). The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin (4-HO-NMT).

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.

'''N-Ethyltryptamine (NET), also abbreviated as NETP', is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N''-diethyltryptamine (DET).

Pinoline is a β-carboline and methoxylated tryptoline (5-methoxytryptoline) long claimed to be produced in the pineal gland during the metabolism of melatonin, however its pineal occurrence remains controversial. Its IUPAC name is 6-methoxy-1,2,3,4-tetrahydro-β-carboline, usually abbreviated as 6-MeO-THBC, and its more common name is a contraction of "pineal β-carboline". The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant, and as a monoamine oxidase A inhibitor.

Harmalol is a bioactive β-carboline and a member of the harmala alkaloids.

Bucindolol is a non-selective beta blocker with additional weak alpha-blocking properties and intrinsic sympathomimetic activity in some model systems but not in human hearts. It was under review by the FDA in the United States for the treatment of heart failure in 2009, but was rejected due to issues pertaining to integrity of data submitted.

Tetrahydroharmine (THH), also known as 7-methoxy-1,2,3,4-tetrahydroharman (7-MeO-THH), is a fluorescent indole alkaloid and β-carboline that occurs in the tropical liana species Banisteriopsis caapi.

Tetrahydroharman, or tetrahydroharmane, also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a β-carboline and general name for one of two isomers:

Tetrahydroharmol is a bioactive β-carboline and harmala alkaloid. It acts as a reversible inhibitor of monoamine oxidase A.

6-MeO-THH, also known as 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a pinoline) derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). It is mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved), stating that 6-MeO-THH is very similar to the other carbolines. The compound has been isolated from certain plants of the Virola family.

'''N-Methylserotonin, also known as norbufotenin or as 5-hydroxy-N-methyltryptamine (5-HO-NMT'), is a tryptamine alkaloid. Chemically, it is a derivative of serotonin in which a methyl group resides at its alkyl amine. It is also called Nω-methylserotonin (N''ω-methyl-5-hydroxytryptamine) to distinguish it from tryptamine-derived compounds in which a methyl group is bonded to the nitrogen atom of the indole group.

5-MeO-NBpBrT, also known as '5-methoxy-N-(4-bromobenzyl)tryptamine', is an N-substituted member of the 5-methoxytryptamine family of compounds. Like other such compounds, it acts as an antagonist for the serotonin 5-HT2A receptor, with a claimed 100-fold selectivity over the closely related serotonin 5-HT2C receptor. While N-benzyl substitution of psychedelic phenethylamines often results in potent serotonin 5-HT2A agonists, it had been thought that N-benzyltryptamines show much lower efficacy and are either very weak partial agonists or antagonists at the serotonin 5-HT2A receptor, though mor