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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:
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

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. 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

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Certificates of Analysis (COA)

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

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Ruan, X., et al.
Huaxue Xuebao, 66, 1731-1731 (2008)
"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)
A Sparatore et al.
European journal of drug metabolism and pharmacokinetics, 20(2), 135-144 (1995-04-01)
The metabolic fate of 9-methyl 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine (MIQ), a compound with promising pharmacological action on the CNS system, was investigated in the rat after an oral dose of 200 mg/kg, the maximal tolerated dose. Urine and feces were collected, exhaustively extracted
Tooru Kamata et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(2), 281-287 (2005-11-11)
The urinary metabolites of 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) in humans have been investigated by analyzing urine specimens from its users. For the unequivocal identification and accurate quantification of its major metabolites, careful analyses were conducted by gas chromatography/mass spectrometry, liquid chromatography/mass spectrometry
J Sallés et al.
Brain research. Molecular brain research, 20(1-2), 111-117 (1993-10-01)
The activation of phospholipase C (PLC) was examined in membranes of rat cerebral cortex simultaneously exposed to monoaminergic receptor and muscarinic receptor agonists after the treatment of membranes with two alkylating agents, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (100 microM EEDQ) and propylbenzilylcholine (10 nM
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