64226-27-3

Basic information

• Product Name: 6-Methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-aMine
• Synonyms: 6-Methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-aMine
• CAS NO: 64226-27-3
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.27894
• EINECS: -0
• Mol File: 64226-27-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-aMine(64226-27-3)
• EPA Substance Registry System: 6-Methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-aMine(64226-27-3)

Safety Data

• Hazardous Substances Data: 64226-27-3(Hazardous Substances Data)

Upstream product

• 97096-16-7 1,4-dioxaspiro[4.5]decan-8-amine 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 180918-12-1 4-oximinocyclohexanone ethylene ketal 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 96497-56-2 Methanesulfonic acid 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-3-yl ester 
• 20802-22-6 3-hydroxy-6-methoxy-1,2,3,4-tetrahydrocarbazole 
• 51145-59-6 3-benzoyloxy-6-methoxy-1,2,3,4-tetrahydro-carbazole 
• 23510-95-4 4-benzoyloxycyclohexanone 
• 99337-98-1 2-((1R,4R)-4-hydroxycyclohexyl) isoindoline-1,3-dione 
• 104618-32-8 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione 
• 27489-62-9 trans-4-hydroxycyclohexylamine 
• 147009-21-0 N-(6-methoxy-1,2,3,4-tetrahydrocarbazol-3-yl)phthalimide 
• 96497-57-3 3-Azido-6-methoxy-2,3,4,9-tetrahydro-1H-carbazole 

Downstream Products

• 1414848-20-6 C₂₅H₂₇F₃N₂O₅S 

Relevant articles and documents

N,N-Dimethyl-[9-(arylsulfonyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]amines as novel, potent and selective 5-HT6 receptor antagonists

The design, synthesis and SAR of novel tetrahydrocarbazole derivatives having 5-HT6 receptor antagonist activity is presented. The racemic compound 15e was found to possess desirable pharmacokinetic properties, adequate brain penetration and activity in animal models of cognition.

Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors

In humans, 5-HT1D serotonin receptors represent terminal autoreceptors, and there is some evidence that 5-HT1D ligands may be useful in the treatment of migraine. The most widely used 5-HT1D agonist is sumatriptan; however, this agent reportedly displays little selectivity for 5-HT1D versus 5-HT1A receptors. To identify novel serotonergic agents with enhanced 5-HT1D versus 5-HT1A selectivity, we attempted to take advantage of possible differences in the regions of bulk tolerance associated with the 5-position of the 5-HT binding sites for these two populations of receptors. Examination of a series of 5-(alkyloxy)tryptamine derivatives demonstrated that compounds with unbranched alkyl groups of up to eight carbon atoms bind with high affinity at human 5-HT1Dβ receptors (K(i) 300-fold). Branching of the alkyl chain, to 5-[(7,7-dimethylheptyl)oxy]tryptamine (15), results in an agent with somewhat lower affinity (5-HT1Dβ K(i) = 2.3 nM) but with greater (i.e., 400-fold) 5-HT1D versus 5-HT1A selectivity. Replacement of the oxygen atom of 10 with a methylene group (i.e., 20), replacement of the O-proximate methylene with a carbonyl group (i.e., ester 26), or cyclization of the aminoethyl moiety to a carbazole (e.g., 34, 36) or β- carboline (i.e., 37), result in reduced affinity and/or selectivity. None of the compounds examined displayed significant selectivity for 5-HT1Dβ versus 5-HT1Dα sites; nevertheless, compounds 10 (recently shown to behave as a 5- HT1D agonist) and 15 represent the most 5-HT1D versus 5-HT1A selective agents reported to date.

An Alternative Synthesis of 3-Amino-1,2,3,4-tetrahydrocarbazoles

3-Amino-1,2,3,4-tetrahydrocarbazoles are easily prepared from the readily available 3-hydroxy-1,2,3,4-tetrahydrocarbazoles by conversion of the latter to the p-toluene- or methanesulfonate ester, followed by nucleophilic displacement with azide ion.The resulting 3-azido-1,2,3,4-tetrahydrocarbazoles are then catalytically hydrogenated to their 3-amino counterparts.