Tryptamine

Tryptamine
IUPAC name

2-(1H-indol-3-yl)ethanamine
Identifiers
CAS number 61-54-1 Y
PubChem 1150
ChEMBL CHEMBL6640 N
IUPHAR ligand 125
Jmol-3D images Image 1
Properties
Molecular formula C10H12N2
Molar mass 160.22 g mol−1
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.[1]

Tryptamine is also the backbone for a group of compounds known collectively as tryptamines. This group includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.[2]

Contents

Plants containing tryptamine

Many if not all plants contain small amounts of tryptamine which is an intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid (heteroauxin).[3] Higher concentrations can be found in many Acacia species.

Tryptamine acts as a natural pesticide in plants.[4]

Tryptamine derivatives

The best-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 tables below list some commonly encountered substituted tryptamines.

The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: LSD, ibogaine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.


Selected Tryptamines (see also Table of naturally occurring tryptamines)
Short Name Origin Rα R4 R5 RN1 RN2 Full Name
Bufotenin Natural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
DMT Natural H H H CH3 CH3 N,N-dimethyltryptamine
Melatonin Natural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine
5-MeO-DMT Natural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
NMT Natural H H H H CH3 N-methyltryptamine
Psilocybin Natural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
Psilocin Natural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
Serotonin Natural H H OH H H 5-hydroxytryptamine
N-methylserotonin Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine
Tryptophan Natural COOH H H H H α-carboxyltryptamine
AET artificial CH2CH3 H H H H α-ethyltryptamine
AMT artificial CH3 H H H H α-methyltryptamine
DALT artificial H H H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine
DET artificial H H H CH2CH3 CH2CH3 N,N-diethyltryptamine
DiPT artificial H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
DPT artificial H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
5-MeO-AMT artificial CH3 H OCH3 H H 5-methoxy-α-methyltryptamine
5-MeO-DALT artificial H H OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine
4-HO-DET artificial H OH H CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine
O-Acetylpsilocin artificial 4-acetoxy-N,N-diethyltryptamine
4-HO-DIPT artificial H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT artificial H H OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine
4-HO-MiPT artificial H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
Sumatriptan artificial H H SO2NHCH3 CH3 CH3 5-methylaminosulfonyl-N,N-dimethyltryptamine
Zolmitriptan artificial
Short Name Origin Rα R4 R5 RN1 RN2 Full Name

Synthesis

The Abramovitch–Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamines starting from a beta-Carboline [5]

See also

References

  1. ^ Jones R.S. (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in neurobiology 19 (1–2): 117–139. doi:10.1016/0301-0082(82)90023-5. 
  2. ^ Effects of tryptamine mediated through 2 states of the 5-HT ...
  3. ^ Takahashi, Dean Nobutaka, Chemistry of Plant Hormones, CRC Press
  4. ^ MI Accumulation of Tryptamine in Barley Leaves Irradiated with UV light, Hisashi Mayagawa, Hiroshi Toda, Tetsu Tsurushima, Tamio Ueno, Jiko Shishiyama, Pesticide Research Institute, Faculty of Agriculture, Kyoto University, Kyoto 606-01, Japan, Bioscience, Biotechnology, Biochemistry, 58(9), 1723-1724, 1994
  5. ^ 880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and -carbolines R. A. Abramovitch and D. Shapiro J. Chem. Soc., 1956, 4589 - 4592, doi:10.1039/JR9560004589

External links

Psychedelics
5-HT2AR agonists
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
Miscellaneous
Others
Tryptamines

2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DiPT • 4-Acetoxy-DMT • 4-Acetoxy-MiPT • 4-AcO-MET • 4-HO-αMT • 4-HO-DiPT • 4-HO-MET • 4-MeO-DMT • 4-Methyl-αET • 4-Methyl-αMT • 4,5-DHP-DMT • 4,5-MDO-DMT • 4,5-MDO-DIPT • 5-Benzyloxytryptamine • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Ethoxy-αMT • 5-Fluoro-αMT • 5-HO-αMT • 5-HTP • 5-Ethoxy-DMT • 5-Ethyl-DMT • 5-Fluoro-DMT • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-7,N,N-TMT • 5-Methyl-αET • 5-MeO-αET  • 5-MeO-αMT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MALT • 5-MeO-MiPT • 5-MeO-NBpBrT • 5,7-Dihydroxytryptamine • 5-(Nonyloxy)tryptamine • 6-Fluoro-αMT • 7-Methyl-αET • 7-Methyl-DMT • αET • αMT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • DALT • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • EPT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Indorenate • Iprocin • MET • MiPT • MPT • Miprocin • Melatonin • MS-245 • NAS • NMT • Norbaeocystin • Normelatonin • Oxypertine • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine • Zolmitriptan
Amino acids
Endocannabinoids
Gasotransmitters
Monoamines
Purines

Adenosine · ADP · AMP · ATP
Trace amines

3-ITA · 5-MeO-DMT · Bufotenin · DMT · NMT · Octopamine · Phenethylamine · Synephrine · Thyronamine · Tryptamine · Tyramine
Others
See also Template:Neuropeptides

M: PNS

anat(h/r/t/c/b/l/s/a)/phys(r)/devp/prot/nttr/nttm/ntrp

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proc, drug(N1B)