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User:ChelseaThompson/sandbox

ChelseaThompson/sandbox
Names
IUPAC name
6-Methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole
Other names
6-MeO-THBC; 5-MeO-TLN; 6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole; pinoline; 6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline; 6-methoxy-1,2,3,4-tetrahydro-β-carboline; 6-methoxy-tetrahydronorharman; 6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline
Identifiers
  • Key: QYMDEOQLJUUNOF-UHFFFAOYSA-N
Properties
C12H14N2O
Molar mass 202.256 g/mol
Melting point 216 - 224 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pinoline is a methoxylated tryptoline that is produced in the pineal gland during the metabolism of melatonin. Its IUPAC name is 6-methoxy-1,2,3,4-tetrahydro-β-carboline, usually abbreviated as 6-MeO-THBC, and its more common name is a combination of "pineal beta-carboline".[1] The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant[2], and as a monoamine oxidase A inhibitor.[3]

Bausch & Lomb filed a patent for this molecule as a potential drug delivery device to treat various opthalmic disorders in 2006.[4]

Production in mammals edit

Main article: beta-carboline

Synthesis in the pineal gland, structurally related to melatonin, is a beta-carboline, what beta-carbolines do, how pinoline has been confirmed to play a role in those processes

Pinoline is synthesized in the pineal gland and can be synthesized from serotonin through the same 5-hydroxyindole-O-methyltransferase enzyme that is active in the production of melatonin. Pinoline can also be formed from melatonin using the aryl acylamidase enzyme. [5] Due to its structural relation to melatonin, pinoline has been studied in vitro and in vivo in many of the same bioactivities that melatonin participates in.

[1]. [3]

Reuptake inhibitor edit

Process edit

indication in the inhibition of the re-uptake of serotonin and norepinephrine once it inhibits the activity of monoamine oxidase A, creating a build-up of these neurotransmitters in the synapses, also reducing the uptake of serotonin in the CNS

[6]

Effects edit

a build-up of these neurotransmitters in synapses has shown anti-depressant effects; discuss studies that have shown the anti-depressant effects in rats

[7]

Antioxidant edit

most of the research surrounding this molecule have been in its antioxidant effects and how those effects compare to melatonin and other beta-carbolines

[8]

mention the significance of having antioxidants in the brain, csf, retinas; pinoline protects against glutamate, NO, OH

[9] [10]

the debate between the effects of pinoline versus melatonin in vivo and in vitro

[11]

Side effects edit

Acts much like melatonin, effects circadian rhythm, development of genital organs, might influence the periodicity of REM sleep

[12] [13]

in chronic doses, can reduce the weight of the pituitary gland, the ovaries, and the uterus; increase the weights of the adrenal glands.

[14]

See also edit

References edit

  1. ^ a b CALLAWAY, J.C., J. GYNTHER, A. Poso, J. VEPSALAINEN, M.M. AIRAKSINEN (1994) The Pictet-Spengler reaction and biogenic tryptamines: Formation of tetrahydro-P-carbolines at physiological pH. J. Heterocyclic Chem. 31: 431–435.
  2. ^ Schiller, Erich (2003). Free Radicals and Inhalation Pathology: Respiratory System, Mononuclear Phagocyte System, Hypoxia and Reoxygenation, Pneumoconioses, and Other Granulomatoses, Cancer (Google Books, page view). Springer. p. 107. ISBN 978-3-540-00201-7. Retrieved 2009-02-14. {{cite book}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  3. ^ a b Cite error: The named reference four was invoked but never defined (see the help page).
  4. ^ Bartels, S. P. (2006) U.S. Patent No. 20,060,292,202 Washington, DC: U.S.
  5. ^ HARDELAND, R., R.J. REITER, B. POEGGLER, D-X. TAN (1993) The significance of metabolism of the neurohormone melatonin: Antioxidative protection and formation of bioactive substances. Neurosci. Biobehav. Rev. 17: 347–357.
  6. ^ Pahkla, R., Zilmer, M., Kullisaar, T., Rago, L. (1998). "Comparison of the antioxidant activity of melatonin and pinoline in vitro". J. Pineal Research, 24, 96-101.
  7. ^ Pahkla, R., Kask, A., Rago, L. (1999). "Differential effects of beta-carbolines and antidepressants on rat exploratory activity in the elevated zero-maze". Pharmacology Biochemistry and Behavior, 65(4), 737-742.
  8. ^ Garcia, J. J., et al. (1999). J. of Bioenergetics and Biomembranes, 31(6), 609-615.
  9. ^ Herrera, F., et al. (2001). "Glutamate induces oxidative stress not mediated by glutamate receptors or cystine transporters: protective effect of melatonin and other antioxidants". J. Pineal Research, 31, 356-362.
  10. ^ Milano-Plano, S. et al. (2010). "Melatonin and structurally-related compounds protect synaptosomal membranes from free radical damage". International Journal of Molecular Sciences, 11, 312-328.
  11. ^ Pless, G., Frederiksen, T. J. P., Garcia, J. J., & Reiter, R. J. (1999). "Pharmacological aspects of N-acetyl-5-methoxytryptamine (melatonin) and 6-methoxy-1,2,3,4-tetrahydro-beta-carboline (pinoline) as antioxidants: Reduction of oxidative damage in brain region homogenates". Journal of Pineal Research, 26(4), 236-246. doi: 10.1111/j.1600-079X.1999.tb00589.x
  12. ^ Leino, M. et al. (1984). "Effects of melatonin and 6-MeOTHBC in light induced retinal damage: A computerized morphometric method". Life Sciences, 35, 1997-2001.
  13. ^ Rimon, R. et al. (1984). "Pinoline, a beta-carboline derivative in the serum and cerebrospinal fluid of patients with schizophrenia". Annals of Clinical Res., 15, 171-175.
  14. ^ Airaksinen, M. M., and Kari, I. (1981). J. Pineal Research. 3, 25-32.

Category:Beta-Carbolines Category:Phenol ethers

 

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