Science Fair Project Encyclopedia
Tryptamine
| Tryptamine | |
|---|---|
| Chemical name | 3-(2-Aminoethyl)indole |
| Chemical formula | 122 |
| Molecular mass | 160.22 g/mol |
| SMILES | NCCC1=CNC2=C1C=CC=C2 |
Tryptamine (3-(2-aminoethyl)indole) is a monoamine compound that is widespread in nature. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds including indole, beta-carboline and ergoline alkaloids and auxins.
Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are commonly used by humans for their psychoactive effects, which tend to be psychedelic in nature. Prominent examples include psilocybin (from "magic mushrooms") and DMT (from numerous plant sources, e.g. ayahuasca). Many synthetic tryptamines have also been made, including the migraine drug sumatriptan and its relatives. The table below lists some commonly encountered substituted tryptamines.
The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: ergoline alkaloids, LSD, ibogaine and yohimbine.
A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.
| Short Name | Rα | R4 | R5 | RN1 | RN2 | Full Name |
|---|---|---|---|---|---|---|
| AET | CH2CH3 | α-ethyltryptamine | ||||
| AMT | CH3 | α-methyltryptamine | ||||
| serotonin | OH | 5-hydroxytryptamine | ||||
| DET | CH2CH3 | CH2CH3 | N,N-diethyltryptamine | |||
| DiPT | CH(CH3)2 | CH(CH3)2 | N,N-diisopropyltryptamine | |||
| DMT | CH3 | CH3 | N,N-dimethyltryptamine | |||
| DPT | CH2CH2CH3 | CH2CH2CH3 | N,N-dipropyltryptamine | |||
| melatonin | OCH3 | O=CH-CH3 | 5-methoxy-N-acetyltryptamine | |||
| 5-MeO-AMT | CH3 | OCH3 | 5-methoxy-α-methyltryptamine | |||
| bufotenine | OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyltryptamine | ||
| ethocin | OH | CH2CH3 | CH2CH3 | 4-hydroxy-N,N-diethyltryptamine | ||
| iprocin | OH | CH(CH3)2 | CH(CH3)2 | 4-hydroxy-N,N-diisopropyltryptamine | ||
| 5-MeO-DIPT | OCH3 | CH(CH3)2 | CH(CH3)2 | 5-methoxy-N,N-diisopropyltryptamine | ||
| 5-MeO-DMT | OCH3 | CH3 | CH3 | 5-methoxy-N,N-dimethyltryptamine | ||
| miprocin | OH | CH(CH3)2 | CH3 | 4-hydroxy-N-isopropyl-N-methyltryptamine | ||
| psilocin | OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyltryptamine | ||
| psilocybin | OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyltryptamine | ||
| sumatriptan | SO2NHCH3 | CH3 | CH3 | 4-methylaminosulfonyl-N,N-dimethyltryptamine |
See also
External links
- lysergic book Describes Several Tryptamine Journeys
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