Tetrahydroisoquinoline

Structural formula
General
Surname	Tetrahydroisoquinoline
other names	1,2,3,4-tetrahydroisoquinoline
Molecular formula	C 9 H 11 N
Brief description	light yellow liquid
External identifiers / databases
CAS number 91-21-4 EC number 202-050-0 ECHA InfoCard 100.001.864 PubChem 7046 Wikidata Q411677
properties
Molar mass	133.19 g mol −1
Physical state	liquid
density	1.05 g cm −3 (20 ° C)
Melting point	−30 ° C
boiling point	232-233 ° C
solubility	20 g / l in water
Refractive index	1.5668 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 302 + 352-304 + 340-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

As tetrahydroisoquinoline which is usually secondary amine 1,2,3,4-tetrahydroisoquinoline, respectively. This consists of a benzene ring to which piperidine is fused . Alternatively, 5,6,7,8-tetrahydroisoquinoline, which can be described as a pyridine with a fused-on cyclohexane ring , is also possible. The main body of tetrahydroisoquinoline is derived from the amino acid tyrosine .

properties

Tetrahydroisoquinoline has a flash point of 98 ° C.

synthesis

Tetrahydroisoquinoline can be synthesized from phenylethylamine and formaldehyde in an acidic environment with elimination of water with the help of the Pictet-Spengler reaction . By using substituted phenylethylamines or higher aldehydes , derivatives of tetrahydroisoquinoline are also accessible.

use

Some derivatives of tetrahydroisoquinoline have a pharmacological effect and are sometimes used as drugs:

• Muscle relaxants such as tubocurarine
• Antihypertensives such as ACE inhibitors quinapril HCl, or Quinapirilat and moexipril, and debrisoquine. These are all derivatives of 1,2,3,4-tetrahydroisoquinoline.
• Incontinence medicines such as solifenacin .

Tetrahydroisoquinoline alkaloids

• Hydrastine
• Laudanosine
• Noscapine
• Salsolinol

See also

• Tetrahydronaphthalene , an analogous ring system without a nitrogen atom
• Isoquinoline

Individual evidence

1. ↑ ^{a b c d e f g h} Datasheet Tetrahydroisoquinoline (PDF) from Merck , accessed on August 13, 2011.
2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-474.
3. ^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 1684, ISBN 978-0-911910-00-1 .
4. ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009), pp. 1172–1174, ISBN 978-3-13-558405-8 ; also online with biannual additions and updates.
5. ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009), pp. 912-913, ISBN 978-3-13-558405-8 ; also online with biannual additions and updates.
6. ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009), pp. 1271–1272, ISBN 978-3-13-558405-8 ; also online with biannual additions and updates.