5-Methoxytryptamines

Melatonin, an indoleamine, is a natural compound produced by various organisms, including bacteria and eukaryotes. Its discovery in 1958 by Aaron B. Lerner and colleagues stemmed from the isolation of a substance from the pineal gland of cows that could induce skin lightening in common frogs. This compound was later identified as a hormone secreted in the brain during the night, playing a crucial role in regulating the sleep-wake cycle, also known as the circadian rhythm, in vertebrates.

Ibogaine is a psychoactive indole alkaloid derived from plants such as Tabernanthe iboga, characterized by hallucinogenic and oneirogenic effects. Traditionally used by Central African foragers, it has undergone controversial research for the treatment of substance use disorders. Ibogaine exhibits complex pharmacology by interacting with multiple neurotransmitter systems, notably affecting opioid, serotonin, sigma, and NMDA receptors, while its metabolite noribogaine primarily acts as a serotonin reuptake inhibitor and κ-opioid receptor agonist.

5-MeO-DMT, also known as '5-methoxy-N,N-dimethyltryptamine, as well as O-methylbufotenin or mebufotenin', is an atypical psychedelic drug, entheogen, and alkaloid of the tryptamine and 5-methoxytryptamine families. It is found naturally in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad (Incilius alvarius, formerly Bufo alvarius). It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five

5-MeO-DiPT, also known as '5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and distinct effects from other serotonergic tryptamines, including some stimulant- and entactogen-like effects, robust tactile and sexual enhancement, and only light hallucinogenic effects. The drug is usually taken orally, but may also be used by other routes.

Metralindole (Inkazan) is a reversible inhibitor of monoamine oxidase A (RIMA) which was investigated in Russia as a potential antidepressant. It is structurally and pharmacologically related to pirlindole.

Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides, Tabernaemontana divaricata and Ervatamia yunnanensis. It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine. It has been demonstrated in animals to have similar anti-addictive properties to ibogaine itself. It also potentiates the effects of barbiturates. Under UV-A and UV-B light its crystals fluore

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.

Oxametacin (or oxamethacin) is a non-steroidal anti-inflammatory drug.

5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as 'α,O-dimethylserotonin (α,O-DMS or Alpha-O'), is a psychedelic drug of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT. The drug is said to be the most potent psychedelic of the simple indolealkylamines (i.e., tryptamines). It is taken orally and is used at doses of 2 to 4mg.

5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or '''O-methylserotonin and as mexamine', is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to occur naturally in the pineal gland of the brain. It is formed via O-methylation of serotonin or N''-deacetylation of melatonin.

Indorenate (TR-3369), is a tryptamine derivative which acts as an agonist at the 5-HT1A, 5-HT1B and 5-HT2C serotonin receptors. It has anxiolytic, antihypertensive and anorectic effects, predominantly through action at 5-HT1A, but with some contribution from the 5-HT1B and 5-HT2C subtypes, and possibly some other non-serotonergic targets also.

5-MeO-DALT, also known as '''N,N-diallyl-5-methoxytryptamine or as foxtrot''', is a psychedelic drug of the tryptamine and 5-methoxytryptamine families. It is taken orally.

5-MeO-MiPT, also known as '5-methoxy-N-methyl-N-isopropyltryptamine or by its nickname Moxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and unusual effects compared to other psychedelic tryptamines. At low doses, its effects include stimulation, tactile and sexual enhancement, some MDMA-like entactogenic effects, and introspective and mild perceptual changes with few or no psychedelic visuals or time dilation, whereas at higher doses, it produces 5-MeO-DMT-like classical psychedelic effects. It is usually taken orally or smoked.

5-MeO-DET, also known as '5-methoxy-N,N-diethyltryptamine' is a psychedelic drug of the tryptamine family related to 5-MeO-DMT. It is taken orally but can also be used parenterally.

5-MeO-pyr-T, also known as '5-methoxy-N,N-tetramethylenetryptamine or as 5-methoxy-3-(2-pyrrolidinoethyl)indole', is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and pyrrolidinylethylindole families. It is the 5-methoxy analogue of pyr-T and the derivative of 5-MeO-DMT and 5-MeO-DET in which their N,N-dialkyl groups have been cyclized into a pyrrolidine ring.

6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin. 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin through hydroxylation. Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors. It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin.

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.

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

'5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), also known as 7-Me-5-MeO-DMT', is a tryptamine derivative which acts as a partial agonist at the 5-HT2 serotonin receptors, with an EC50 of 63.9 nM and an efficacy of 66.2% at 5-HT2A (vs 5-HT), and weaker activity at 5-HT2B and 5-HT2C. In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite hi

5,6-MeO-MiPT, also known as '5,6-dimethoxy-N-methyl-N-isopropyltryptamine', is a chemical compound of the tryptamine family. It is the 5,6-dimethoxy derivative of methylisopropyltryptamine (MiPT) and is an analogue of 5-MeO-MiPT. In his 1991 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin listed the dose as greater than 75mg orally and the duration as unknown. The drug produced few to no effects at doses of up to 75mg orally. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MeO-MiPT. However, the drug has been found to have aboli

BW-723C86 is a tryptamine derivative drug which acts as a 5-HT2B receptor agonist. It has anxiolytic effects in animal studies, and is also used for investigating the function of the 5-HT2B receptor in a range of other tissues.