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Tetrahydroisoquinoline information


Tetrahydroisoquinoline
Names
Preferred IUPAC name
1,2,3,4-Tetrahydroisoquinoline
Identifiers
CAS Number
  • 91-21-4 checkY
3D model (JSmol)
  • Interactive image
Abbreviations TIQ, THIQ
ChEMBL
  • ChEMBL14346 checkY
ChemSpider
  • 6779 checkY
ECHA InfoCard 100.001.864 Edit this at Wikidata
EC Number
  • 202-050-0
PubChem CID
  • 7046
RTECS number
  • NX4900000
UNII
  • 56W89FBX3E checkY
CompTox Dashboard (EPA)
  • DTXSID6026115 Edit this at Wikidata
InChI
  • InChI=1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2 checkY
    Key: UWYZHKAOTLEWKK-UHFFFAOYSA-N checkY
  • InChI=1/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
    Key: UWYZHKAOTLEWKK-UHFFFAOYAB
SMILES
  • c1ccc2c(c1)CCNC2
Properties
Chemical formula
C9H11N
Molar mass 133.19 g/mol
Appearance Deep yellow liquid
Density 1.05 g/mL
Melting point −30 °C (−22 °F; 243 K)
Boiling point 235 to 239 °C (455 to 462 °F; 508 to 512 K)
Hazards
GHS labelling:[1]
Pictograms
GHS05: CorrosiveGHS06: ToxicGHS08: Health hazard
Signal word
Danger
Hazard statements
H301, H310, H314, H332, H371, H412
Precautionary statements
P260, P261, P262, P264, P270, P271, P273, P280, P301+P310, P301+P330+P331, P302+P350, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P309+P311, P310, P312, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
Flash point 99 °C (210 °F; 372 K) (closed cup)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Tetrahydroisoquinoline (TIQ or THIQ) is an organic compound with the chemical formula C9H11N. Classified as a secondary amine, it is derived from isoquinoline by hydrogenation. It is a colorless viscous liquid that is miscible with most organic solvents. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs.[2][3]

  1. ^ "1,2,3,4-Tetrahydroisoquinoline". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  2. ^ Mitchenson, Andrew (2000). "Saturated nitrogen heterocycles". Journal of the Chemical Society, Perkin Transactions 1 (17): 2862–2892. doi:10.1039/A908537H.
  3. ^ Cite error: The named reference Scott was invoked but never defined (see the help page).

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Tetrahydroisoquinoline

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Tetrahydroisoquinoline (TIQ or THIQ) is an organic compound with the chemical formula C9H11N. Classified as a secondary amine, it is derived from isoquinoline...

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Isoquinoline

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aldehyde forms an imine, which undergoes a cyclization to form a tetrahydroisoquinoline instead of the dihydroisoquinoline. In enzymology, the (S)-norcoclaurine...

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Clazolam

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as isoquinazepon, is a drug which is a fused benzodiazepine and tetrahydroisoquinoline derivative. It was developed in the 1960s but was never marketed...

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Berberine

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the biosynthetic pathway, only the phenethylamine fragment of the tetrahydroisoquinoline ring system is formed via DOPA; the remaining carbon atoms come...

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Coclaurine

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harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine...

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Morphine

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disease. Morphine is biosynthesized in the opium poppy from the tetrahydroisoquinoline reticuline. It is converted into salutaridine, thebaine, and oripavine...

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Quetiapine

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Salsolinol

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Salsolinol has been used as a starting material to prepare some tetrahydroisoquinoline-based prospective drugs. Salsolinol is found in several edible plants...

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Ketamine

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LSD

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Erythravine

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Erythravine is a tetrahydroisoquinoline alkaloid found in the plant Erythrina mulungu and other species of the genus Erythrina. Some laboratory research...

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Phencyclidine

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Anhalidine

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Anhalidine is a naturally occurring tetrahydroisoquinoline based alkaloid which can be isolated from Lophophora williamsii; it has also been detected other...

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Risperidone

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Decahydroisoquinoline

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Decahydroisoquinoline can be formed by the hydrogenation of isoquinoline or tetrahydroisoquinoline. There are four stereoisomers of decahydroisoquinoline which differ...

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Doxacurium chloride

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action. Partial saturation of the benzylisoquinoline ring to the tetrahydroisoquinoline ring provided an even further increase in potency of the molecules...

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Dopamine

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Amitriptyline

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Haloperidol

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Levosulpiride

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Promethazine

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Phenylalanine

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Drotaverine

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IUPAC name (Z)-1-(3,4-diethoxybenzylidene)-6,7-diethoxy-1,2,3,4-tetrahydroisoquinoline CAS Number 14009-24-6 N PubChem CID 1712095 DrugBank DB06751 Y ChemSpider...

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Modafinil

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Aripiprazole

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Erythrina

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Erythravine is tetrahydroisoquinoline alkaloid from Erythrina mulungu, studied for possible anxiolytic properties....

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