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Tryptamine

HCID 1150
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
61-54-1
Standard SMILES
NCCc1c[nH]c2ccccc12
InChIKey
APJYDQYYACXCRM-UHFFFAOYSA-N
Molecular formula
C10H12N2
Average molar mass
160.22 g/mol
Monoisotopic mass
160.10004839

Overview

Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is a member of tryptamines, an aminoalkylindole, an indole alkaloid and an aralkylamino compound. It is a conjugate base of a tryptaminium.

Names & identifiers

Preferred name
Tryptamine
IUPAC
2-(1H-indol-3-yl)ethanamine
English name
Tryptamine
Molecular formula
C10H12N2
Molecular weight
160.22

Names & synonyms

tryptamine61-54-12-(1H-Indol-3-yl)ethanamine3-(2-aminoethyl)indole1H-Indole-3-ethanamine2-(3-Indolyl)ethylamine2-(1H-Indol-3-Yl)Ethan-1-AmineIndole, 3-(2-aminoethyl)-beta-(3-Indolyl)ethylamine422ZU9N5TVCHEBI:16765DTXSID2075340
Show more names
L-TRYPTAMINETRIPTAMINETRYPTAMINE CAS 61-54-12-(1H-indol-3-yl)ethan-1-aMine hydrochlorideb mk-2ryptamine
NSC-1652123-[2-Aminoethyl]indoleRefChem:900684DTXCID3042922200-510-5TryptaminIndol-3-ethylamine2-(Indol-3-yl)ethylamine

Database identifiers

CAS
61-54-1
PubChem CID
1150
DTXSID
DTXSID2075340
ChEMBL
CHEMBL6640
ChEBI
CHEBI:16765
UNII
422ZU9N5TV
EC Number
200-510-5

Properties

Computed structural propertiesFilling in

XLogP
1.6
Topological polar surface area
41.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
12
Formal charge
0
Complexity
147

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Tryptamines

Pharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesAngular frequency
LogP · 2 items

1.55

1.35

Melting Point114 - 119 °C
Physical DescriptionSolid
Collision Cross Section · 5 items

128.42 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

125.1 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

131.25 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

124.4 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

127.6 Ų [M+H]+

Physicochemical properties

Melting point
113 · 113-116 °C (lit.)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 1.9% (1 of 52) of reports.

Warning

H315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 52 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

REACH registered substance: 2-(indol-3-yl)ethylamine (EC: 200-510-5)

1H-Indole-3-ethanamine: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)

Safety data

F
8-23
wgk
3
rtecs
NL4020000
hs_code
29339990
risk_code
20/21/22-36/37/38-41-37/38-22
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
Xi
safety_code
24/25-36/37/39-36-26
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism
Applications · 4 items

DescriptionTryptamine is a monoamine alkaloid that can be synthesized by decarboxylation of the amino acid tryptophan. Notably, tryptamine can be found in fungi, plants, Amphibia, animals, and microbes. Tryptamine has an indole ring structure and a fused double ring that is composed of a benzene ring and a pyrrole ring, linked to an amino group by 2-carbon side chain. The indole ring is the vital nucleus of many complex natural products that have significance in drug discovery as well as some synthetic and non-synthetic drugs that are based on tryptamine skeleton. The chemical’s distinct structure is an approximation to the neurotransmitter serotonin as well-known drugs and hallucinogens. Tryptamine’s significance as psychedelic drugs, neuromodulator, and neurotransmitter is well understood due to its presence in mammalian brain in small amounts.

DescriptionTryptamine is an indole alkaloid and intermediate in the biosynthesis of serotonin and the phytohormone melatonin in plants. It increases the levels of the terpenoid indole alkaloids ajmalicine, strictosidine, and catharanthine in cultures of C. roseus. Tryptamine is also a product of tryptophan metabolism in mammals. Tryptamine derivatives have been synthetically produced as hallucinogenic drugs of abuse that act on the serotonergic system.

UsesTryptamine is a monoamine alkaloid found in plants. Tryptamine is commonly used in the preparation of biologically active compounds such as neurotransmitters and psychedelics.

General DescriptionTryptamines which are usually found in plants, fungi, animals, etc. are categorized under the monoamine alkaloids class of compounds.

Preparation methods · 1 item

Related reactions

319 records
New reaction record
HRID 11859 reaction equation
HRID 11859As reactantuspto-grants-2006_08
HRID 14717 reaction equation
HRID 14717As reactantuspto-grants-2010_06
HRID 27236 reaction equation
HRID 27236As reactantuspto-grants-1980_09
HRID 44137 reaction equation
HRID 44137As reactantuspto-grants-2013_09
HRID 54849 reaction equation
HRID 54849As reactantuspto-grants-1997_04
HRID 62586 reaction equation
HRID 62586As productuspto-grants-2016_09
HRID 64386 reaction equation
HRID 64386As reactantuspto-grants-2016_09
HRID 64391 reaction equation
HRID 64391As reactantuspto-grants-2016_09
Page 1 of 40

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Nikkaji
J4.816J
Boiling point
137 °C/0.15 · 137 °C/0.15 mmHg (lit.)
Density
0.9787 · 0.9787 (rough estimate)
refractive index
1.621 · 1.6210 (estimate)
Flash point
185 °C · 185 °C
storage temp.
2 · 2-8°C
solubility
1 g/L · water: soluble1g/L at 20°C
pka
10.2 · 10.2(at 25℃)
form
crystalline
color
white
PH
11.07 · 11.07 (10g/l, H2O, 24.7℃)
Water Solubility
negligible
Sensitive
Air Sensitive
Merck
14 · 14,9796
BRN
125513 · 125513
Major Application
cleaning productscosmeticsfood and beveragespersonal care
InChI
1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2
InChIKey
APJYDQYYACXCRM-UHFFFAOYSA-N
SMILES
NCCc1c[nH]c2ccccc12
CAS DataBase Reference
61 · 61-54-1(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
422 ZU9N5TV · 422ZU9N5TV
NIST Chemistry Reference
1 H-Indole-3-ethanamine · 1H-Indole-3-ethanamine(61-54-1)
EPA Substance Registry System
Tryptamine (61-54-1)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302-H317-H318
Precautionary statements
261 · P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
Hazard Codes
Xi
Risk Statements
20 · 20/21/22-36/37/38-41-37/38-22
Safety Statements
24 · 24/25-36/37/39-36-26
WGK Germany
3 · 3
RTECS
4020000 · NL4020000
F
8 · 8-23
HazardClass
IRRITANT
HS Code
28259080 · 28259080
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Sens. 1A
REACH Registrations
Active
Hazard statements
H302-H317-H318
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Skin Sens. 1A
Precautionary statements
P261-P264-P280-P301+P312-P302+P352-P305+P351+P338

PreparationTryptamine, a monoamine alkaloid containing an indole ring structure is derived by the decarboxylation of amino acid tryptophan.The synthesis of tryptamines is typically conducted following a classic route starting with a Mannich reaction of an indole heterocycle, followed by quaternization of the amine, nucleophilic substitution with highly toxic cyanide and final reduction.

Upstream & downstream products

Upstream raw materials

1H-Indole-3-propanoic acid, α-amino-2,3-dihydro-2-oxo-, (αS)-L-5-HydroxytryptophanL-KYNURENINE

Downstream products

Vinpocetine1,2,3,4-TETRAHYDRO-9H-PYRIDO[3,4-B]INDOLEN,N-DimethyltryptamineVincamineN-(p-Coumaroyl) Serotonin1-TRIFLUOROMETHYL-2,3,4,9-TETRAHYDRO-1H-B-CARBOLINEN-METHYL-N-ISOPROPYLTRYPTAMINE(MIPT)TETRAHYDROALSTONINE3-Ethylindole2-cyano-N-[2-(1H-indol-3-yl)ethyl]acetamideN-(2-INDOL-3-YLETHYL)(4-METHYLPHENYL)FORMAMIDEN-(2-INDOL-3-YLETHYL)-3-PHENYLPROP-2-ENAMIDE
Additional notes · 1 item

DefinitionChEBI: Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium.