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134228

Sigma-Aldrich

5-Methyltryptamine hydrochloride

98%

Synonym(s):

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

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250 MG
€74.80

About This Item

Empirical Formula (Hill Notation):
C11H14N2 · HCl
CAS Number:
1010-95-3
Molecular Weight:
210.70
EC Number:
213-777-8
MDL number:
MFCD00012683
UNSPSC Code:
12352100
PubChem Substance ID:
24848138
NACRES:
NA.22

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Assay

98%

form

powder

mp

289-292 °C (dec.) (lit.)

solubility

H2O: soluble 50 mg/mL, clear, yellow

functional group

amine

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[1]. It was used as internal standard in the determination of urinary metabolites of 5-methoxy-N,N-diisopropyltryptamine in humans[2]. It was used as reactant in:
  • synthesis of kinesin spindle protein (KSP) inhibitors[3]
  • intramolecular furan Diels-Alder reactions[4]
  • Pictet-Spengler-like reactions[5]
  • reactant in synthesis of kinesin spindle protein (KSP) inhibitors[3]
  • reactant in intramolecular furan Diels-Alder reactions[4]
  • reactant in Pictet-Spengler-like reactions[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBD5596V
S21034
06703JE
08721BW
06830LD

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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)
Ruan, X., et al.
Huaxue Xuebao, 66, 1731-1731 (2008)
Fokas, D., et al.
Tetrahedron Letters, 44, 5137-5137 (2003)
I Litosch et al.
The Journal of biological chemistry, 260(30), 16052-16055 (1985-12-25)
5-Methyltryptamine, through a GTP-dependent mechanism, stimulated breakdown of endogenous [3H]inositol-labeled phosphoinositides in membranes prepared from blowfly salivary gland homogenates through a phospholipase C exhibiting a pH optimum of approximately 7.0. Unlabeled membranes, prepared from salivary gland homogenates, hydrolyzed exogenous [3H]phosphatidylinositol
M A Wallace et al.
The Journal of pharmacology and experimental therapeutics, 255(3), 1296-1300 (1990-12-01)
Stimulation of phosphoinositide-specific phospholipase C (PLC) by muscarinic cholinergic and serotoninergic agonists was measured in rat brain cortical membranes by using exogenously supplied substrates. Serotonin, tryptamine, 5-fluorotryptamine and 5-methyltryptamine stimulated PLC with EC50 values of 1.7, 11.2, 15.0, and 29.4
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