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Encyclopedia > Tryptamine
Tryptamine
Chemical name 3-(2-Aminoethyl)indole
Chemical formula C10H12N2
Molecular mass 160.22 g/mol
SMILES NCCC1=CNC2=C1C=CC=C2
Chemical structure of Tryptamine

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.

General structure of substituted tryptamines
General structure of substituted tryptamines


Substituted tryptamines, tabulated by structure
Short Name Rα R4 R5 RN1 RN2 Full Name
serotonin OH 5-hydroxytryptamine
melatonin OCH3 O=CH-CH3 5-methoxy-N-acetyltryptamine
sumatriptan SO2NHCH3 CH3 CH3 4-methylaminosulfonyl-N,N-dimethyltryptamine
DMT CH3 CH3 N,N-dimethyltryptamine
DET CH2CH3 CH2CH3 N,N-diethyltryptamine
DPT CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
DiPT CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
bufotenine OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
5-MeO-DMT OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
5-MeO-DIPT OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine
psilocin OH CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
psilocybin OPO3H2 CH3 CH3 4-phosphoryloxy-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
miprocin OH CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
AMT CH3 α-methyltryptamine
AET CH2CH3 α-ethyltryptamine
5-MeO-AMT CH3 OCH3 5-methoxy-α-methyltryptamine

See also

External links

  • Tryptamine FAQ (http://www.erowid.org/psychoactives/faqs/faqs_tryptamine.shtml)


Tryptamines edit (http://en.wikipedia.org/w/index.php?title=Template:Tryptamines&action=edit)

{5-MeO-AMT} {5-MeO-DIPT} {5-MeO-DMT} {AET} {AMT} {Bufotenin} {DET} {DIPT} {DMT} {DPT} {Ethocin} {Iprocin} {Melatonin} {Psilocin} {Psilocybin} {Rizatriptan} {Serotonin} {Sumatriptan} {Tryptamine}

Hallucinogenic tryptamines edit (http://en.wikipedia.org/w/index.php?title=Template:Hallucinogenic_tryptamines&action=edit)

{5-MeO-AMT} {5-MeO-DIPT} {5-MeO-DMT} {AMT} {Bufotenin} {DET} {DIPT} {DMT} {DPT} {Ethocin} {Iprocin} {Psilocin} {Psilocybin}


  Results from FactBites:
 
Tryptamines (229 words)
However, the effects produced by consuming preparations of dried or brewed mushrooms are far less predictable and largely depend on the particular mushrooms used and the age and preservation of the extract.
There are many species of "magic" mushrooms that contain varying amounts of these tryptamines, as well as uncertain amounts of other chemicals.
As a consequence, the hallucinogenic activity, as well as the extent of toxicity produced by various plant samples, are often unknown.
  More results at FactBites »

 
 

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