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
CAS Number	20315-68-8;
	InChI Key: QYMDEOQLJUUNOF-UHFFFAOYSA-N;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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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

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

Process

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

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

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

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]

References

^ ^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.
^ 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)
^ ^a ^b Cite error: The named reference four was invoked but never defined (see the help page).
^ Bartels, S. P. (2006) U.S. Patent No. 20,060,292,202 Washington, DC: U.S.
^ 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.
^ 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.
^ 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.
^ Garcia, J. J., et al. (1999). J. of Bioenergetics and Biomembranes, 31(6), 609-615.
^ 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.
^ 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.
^ 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
^ 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.
^ 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.
^ Airaksinen, M. M., and Kari, I. (1981). J. Pineal Research. 3, 25-32.

Category:Beta-Carbolines Category:Phenol ethers

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[Callaway-1] 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)

[four-3] 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.

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