Tryptamine

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Tryptamine
IUPAC name

2-(1H-Indol-3-yl)ethanamine

Identifiers
CAS number 61-54-1 YesY
PubChem 1150
ChEMBL CHEMBL6640 N
IUPHAR ligand 125
Jmol-3D images Image 1
Properties
Molecular formula C10H12N2
Molar mass 160.22 g mol−1
Appearance white to orange crystalline powder[1]
Melting point 113-116˚C[1]
Boiling point 137˚C[1]
Solubility in water negligible solubility in water[1]
Hazards
Flash point 185˚C[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which it derives its name. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.[2]

The tryptamine chemical structure is the backbone for a group of compounds termed collectively 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.[3]

Plants containing tryptamine

Many plants contain small amounts of tryptamine, for example, as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid.[4] Higher concentrations can be found in many Acacia species.

Role in vertebrates

Tryptamine acts as a serotonin releasing agent[5] and a serotonergic activity enhancer.[6] It is metabolised by MAO-A and MAO-B.[7]

Tryptamine derivatives

Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are sometimes used by humans and other animals, notably, the Jaguar, for their psychotropic effects. A Jaguar is seen eating yage (banisteriopsis caapi), a plant with high concentrations of the tryptamines harmine and harmaline, in an interesting clip borrowed from the "Peculiar Potions" episode of BBC's series "Weird Nature". Prominent examples of tryptamines include psilocybin (from "Psilocybin 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 tryptamines.

General structure of substituted tryptamines

The tryptamine structure, in particular its indole ring, may be 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
TryptamineNatural H H H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
BufoteninNatural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
Nω-methylserotonin (norbufotenin)Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine
SerotoninNatural H H OH H H 5-hydroxytryptamine
DMTNatural H H H CH3 CH3 N,N-dimethyltryptamine
MelatoninNatural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine
5-Bromo-DMTNatural H H Br CH3 CH3 5-bromo-N,N-dimethyltryptamine
5-MeO-DMTNatural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
5-MeO-NMTNatural H H OCH3 CH3 H 5-methoxy-N-methyltryptamine
NMTNatural H H H H CH3 N-methyltryptamine
NorbaeocystinNatural H OPO3H2 H H H 4-phosphoryloxy-tryptamine
BaeocystinNatural H OPO3H2 H CH3 H 4-phosphoryloxy-N-methyl-tryptamine
PsilocybinNatural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
PsilocinNatural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
TryptophanNatural COOH H H H H α-carboxyltryptamine
αET artificial CH2CH3 H H H H α-ethyltryptamine
αMT 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-αMT 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
4-AcO-DMT artificial H OCOCH3 H CH3 CH3 4-acetoxy-N,N-dimethyltryptamine
4-HO-MET artificial H OH H CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine
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 CH2SO2NHCH3 CH3 CH3 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine
Zolmitriptan artificial H H -(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine
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 β-carboline.[8]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 "http://www.chemicalbook.com/ProductChemicalPropertiesCB8192006_EN.htm"
  2. ↑ 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. 
  3. ↑ Jiang, Zhen; Mutch, Elaine; Blain, Peter G.; Williams, Faith M. (2006). "Conversion of trichloroethylene to chloral using occupationally relevant levels". Toxicology 226: 76. doi:10.1016/j.tox.2006.05.102. 
  4. ↑ Nobutaka Takahashi (1986). Chemistry of Plant Hormones. CRC Press. ISBN 9780849354700. 
  5. ↑ Wölfel, Reinhard; Graefe, Karl-Heinz (1992). "Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter". Naunyn-Schmiedeberg's Archives of Pharmacology 345 (2): 129–36. doi:10.1007/BF00165727. PMID 1570019. 
  6. ↑ Shimazu, S; Miklya, I (2004). "Pharmacological studies with endogenous enhancer substances: Beta-phenylethylamine, tryptamine, and their synthetic derivatives". Progress in neuro-psychopharmacology & biological psychiatry 28 (3): 421–7. doi:10.1016/j.pnpbp.2003.11.016. PMID 15093948. 
  7. ↑ Sullivan, James P.; McDonnell, Leonard; Hardiman, Orla M.; Farrell, Michael A.; Phillips, Jack P.; Tipton, Keith F. (1986). "The oxidation of tryptamine by the two forms of monoamine oxidase in human tissues". Biochemical Pharmacology 35 (19): 3255–60. doi:10.1016/0006-2952(86)90421-1. PMID 3094536. 
  8. ↑ Abramovitch, R. A.; Shapiro, D. (1956). "880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and ?-carbolines". Journal of the Chemical Society (Resumed): 4589. doi:10.1039/JR9560004589. 

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