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134228

Sigma-Aldrich

5-Methyltryptamine hydrochloride

98%

Synonym(s):

3-(2-Aminoethyl)-5-methylindole hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C11H14N2 · HCl
CAS Number:
Molecular Weight:
210.70
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

powder

mp

289-292 °C (dec.) (lit.)

solubility

H2O: soluble 50 mg/mL, clear, yellow

SMILES string

Cl.Cc1ccc2[nH]cc(CCN)c2c1

InChI

1S/C11H14N2.ClH/c1-8-2-3-11-10(6-8)9(4-5-12)7-13-11;/h2-3,6-7,13H,4-5,12H2,1H3;1H

InChI key

RBHDFGBPJGEYCK-UHFFFAOYSA-N

Application

5-Methyltryptamine hydrochloride was used to study the mechanism of metabolism of 9-methyl 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine in rats. It was used as internal standard in the determination of urinary metabolites of 5-methoxy-N,N-diisopropyltryptamine in humans. It was used as reactant in:
  • synthesis of kinesin spindle protein (KSP) inhibitors
  • intramolecular furan Diels-Alder reactions
  • Pictet-Spengler-like reactions
  • reactant in synthesis of kinesin spindle protein (KSP) inhibitors
  • reactant in intramolecular furan Diels-Alder reactions
  • reactant in Pictet-Spengler-like reactions

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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"Pictet-Spengler-like" Synthesis of Tetrahydro-beta-carbolines under Hydrolytic Conditions. Direct Use of Azalactones as Phenylacetaldehyde Equivalents.
James E. Audia et al.
The Journal of organic chemistry, 61(22), 7937-7939 (1996-11-01)
Fokas, D., et al.
Tetrahedron Letters, 44, 5137-5137 (2003)
Ruan, X., et al.
Huaxue Xuebao, 66, 1731-1731 (2008)
Characterization of eight biogenic indoleamines as substrates for type A and type B monoamine oxidase.
O Suzuki et al.
Biochemical pharmacology, 30(11), 1353-1358 (1981-06-01)
J Sallés et al.
Psychopharmacology, 154(2), 115-125 (2001-04-21)
One of the major pathways for neurotransmitter signaling involves phosphoinositide-specific and G-protein-dependent phospholipase C-beta (PLC-beta), which stimulates the formation of inositol 1,4,5-trisphosphate and diacylglycerol. Serotonergic and muscarinic-cholinergic signals in the brain are largely mediated through the hydrolysis of phosphoinositides by

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