Tryptamine
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|- | Molar mass | 160.22 g/mol |- | align="center" cellspacing="3" style="border: 1px solid #C0C090; background-color: #F8EABA; margin-bottom: 3px;" colspan="2" | Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
[Chemical infoboxInfobox disclaimer and references] |- |}
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 psychotropic effects. Prominent examples include psilocybin (from "magic mushrooms") and DMT (from numerous plant sources, e.g. chacruna, often used in ayahuasca brews). 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 like 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-ethyl | ||||
| AMT | CH3 | α-methyl | ||||
| serotonin | OH | 5-hydroxy | ||||
| DET | CH2CH3 | CH2CH3 | N,N-diethyl | |||
| DiPT | CH(CH3)2 | CH(CH3)2 | N,N-diisopropyl | |||
| DMT | CH3 | CH3 | N,N-dimethyl | |||
| DPT | CH2CH2CH3 | CH2CH2CH3 | N,N-dipropyl | |||
| melatonin | OCH3 | O=CH-CH3 | 5-methoxy-N-acetyl | |||
| 5-MeO-AMT | CH3 | OCH3 | 5-methoxy-α-methyl | |||
| bufotenine | OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyl | ||
| ethocin | OH | CH2CH3 | CH2CH3 | 4-hydroxy-N,N-diethyl | ||
| iprocin | OH | CH(CH3)2 | CH(CH3)2 | 4-hydroxy-N,N-diisopropyl | ||
| 5-MeO-DIPT | OCH3 | CH(CH3)2 | CH(CH3)2 | 5-methoxy-N,N-diisopropyl | ||
| 5-MeO-DMT | OCH3 | CH3 | CH3 | 5-methoxy-N,N-dimethyl | ||
| Miprocin | OH | CH(CH3)2 | CH3 | 4-hydroxy-N-isopropyl-N-methyl | ||
| psilocin | OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyl | ||
| psilocybin | OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyl | ||
| sumatriptan | SO2NHCH3 | CH3 | CH3 | 5-methylaminosulfonyl-N,N-dimethyl | ||
See also
External links
- [Tryptamine FAQ]
- [Tryptamine Hallucinogens and Consciousness]
- [Lysergic book], describes several tryptamine journeys.
- [User-friendly info on Tryptamines], provided by the TRIP! Project, Toronto Canada.
- [Tryptamind Psychoactives], reference site on tryptamine and other psychoactives.
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
| Psychedelic tryptamines [http://encycl.opentopia.com/ edit] |
|---|
| 4-Acetoxy-DET | 4-Acetoxy-DIPT | α-ET | α-MT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | EIPT | Ethocin | Iprocin | MET | MIPT |5-MeO-α-ET | 5-MeO-α-MT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-DPT | 5-MeO-MIPT | Miprocin | Norbaeocystin | Psilocin | Psilocybin | |
| Tryptamines [http://encycl.opentopia.com/ edit] |
|---|
| 4-Acetoxy-DET > 4-Acetoxy-DIPT | 5-MeO-α-ET | 5-MeO-α-MT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-DPT | 5-MeO-MIPT | α-ET | α-MT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | EIPT | Ethocin | Ibogaine | Iprocin | MET | MIPT | Miprocin | Melatonin | NMT | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan |
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