Chemistry:Indorenate

Indorenate
Identifiers
	IUPAC name methyl 3-amino-2-(5-methoxy-1H-indol-3-yl)propanoate;
CAS Number	73758-06-2 ;
PubChem CID	71987;
ChemSpider	64989 ;
UNII	AV9L041QA4;
Chemical and physical data
Formula	C13H16N2O3
Molar mass	248.282 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(=O)C(CN)c1c[nH]c(ccc2OC)c1c2;
	InChI InChI=1S/C13H16N2O3/c1-17-8-3-4-12-9(5-8)11(7-15-12)10(6-14)13(16)18-2/h3-5,7,10,15H,6,14H2,1-2H3 ; Key:YFEDJMLMWJSRJJ-UHFFFAOYSA-N ;
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Short description: Chemical compound

Indorenate (TR-3369), is a tryptamine derivative which acts as an agonist at the 5-HT_1A, 5-HT_1B and 5-HT_2C serotonin receptors. It has anxiolytic, antihypertensive and anorectic effects, predominantly through action at 5-HT_1A, but with some contribution from the 5-HT_1B and 5-HT_2C subtypes, and possibly some other non-serotonergic targets also.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]

References

↑ "On the effects and mechanism of action of the antihypertensive agent TR 3369 (5-methoxytryptamine beta-methylcarboxylate) in spontaneously hypertensive rats". Journal of Cardiovascular Pharmacology 3 (6): 1306–11. 1981. doi:10.1097/00005344-198111000-00018. PMID 6173531.
↑ "Centrally acting hypotensive agents with affinity for 5-HT1A binding sites inhibit forskolin-stimulated adenylate cyclase activity in calf hippocampus". British Journal of Pharmacology 95 (3): 975–85. November 1988. doi:10.1111/j.1476-5381.1988.tb11728.x. PMID 3207999.
↑ "Behavioural actions of the serotonergic anxiolytic indorenate". Pharmacology Biochemistry and Behavior 37 (1): 83–8. September 1990. doi:10.1016/0091-3057(90)90045-J. PMID 1979877.
↑ "Effects of the intracerebroventricular administration of indorenate and fenfluramine on spontaneous behavior and food intake in rats". Proceedings of the Western Pharmacology Society 34: 465–8. 1991. PMID 1788330.
↑ "Discriminative stimulus properties of indorenate, a serotonin agonist". Journal of Psychiatry & Neuroscience 24 (2): 122–30. March 1999. PMID 10212554.
↑ "Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats". Journal of Psychopharmacology 15 (1): 29–36. March 2001. doi:10.1177/026988110101500106. PMID 11277605.
↑ "Full substitution of the discriminative cue of a 5-HT(1A/1B/2C) agonist with the combined administration of a 5-HT(1B/2C) and a 5-HT(1A) agonist". Behavioural Pharmacology 13 (4): 303–11. July 2002. doi:10.1097/00008877-200207000-00007. PMID 12218511.
↑ "Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors". Pharmacology Biochemistry and Behavior 74 (2): 371–80. January 2003. doi:10.1016/S0091-3057(02)01010-9. PMID 12479957.
↑ "Indorenate modifies a1-adrenergic and benzodiazepine receptor binding in the rat brain: an autoradiography study". The Journal of Pharmacy and Pharmacology 58 (9): 1243–8. September 2006. doi:10.1211/jpp.58.9.0011. PMID 16945183.

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Original source: https://en.wikipedia.org/wiki/Indorenate. Read more

[pmid6173531-1] "On the effects and mechanism of action of the antihypertensive agent TR 3369 (5-methoxytryptamine beta-methylcarboxylate) in spontaneously hypertensive rats". Journal of Cardiovascular Pharmacology 3 (6): 1306–11. 1981. doi:10.1097/00005344-198111000-00018. PMID 6173531.

[pmid3207999-2] "Centrally acting hypotensive agents with affinity for 5-HT1A binding sites inhibit forskolin-stimulated adenylate cyclase activity in calf hippocampus". British Journal of Pharmacology 95 (3): 975–85. November 1988. doi:10.1111/j.1476-5381.1988.tb11728.x. PMID 3207999.

[pmid1979877-3] "Behavioural actions of the serotonergic anxiolytic indorenate". Pharmacology Biochemistry and Behavior 37 (1): 83–8. September 1990. doi:10.1016/0091-3057(90)90045-J. PMID 1979877.

[pmid1788330-4] "Effects of the intracerebroventricular administration of indorenate and fenfluramine on spontaneous behavior and food intake in rats". Proceedings of the Western Pharmacology Society 34: 465–8. 1991. PMID 1788330.

[pmid10212554-5] "Discriminative stimulus properties of indorenate, a serotonin agonist". Journal of Psychiatry & Neuroscience 24 (2): 122–30. March 1999. PMID 10212554.

[pmid11277605-6] "Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats". Journal of Psychopharmacology 15 (1): 29–36. March 2001. doi:10.1177/026988110101500106. PMID 11277605.

[pmid12218511-7] "Full substitution of the discriminative cue of a 5-HT(1A/1B/2C) agonist with the combined administration of a 5-HT(1B/2C) and a 5-HT(1A) agonist". Behavioural Pharmacology 13 (4): 303–11. July 2002. doi:10.1097/00008877-200207000-00007. PMID 12218511.

[pmid12479957-8] "Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors". Pharmacology Biochemistry and Behavior 74 (2): 371–80. January 2003. doi:10.1016/S0091-3057(02)01010-9. PMID 12479957.

[pmid16945183-9] "Indorenate modifies a1-adrenergic and benzodiazepine receptor binding in the rat brain: an autoradiography study". The Journal of Pharmacy and Pharmacology 58 (9): 1243–8. September 2006. doi:10.1211/jpp.58.9.0011. PMID 16945183.

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Identifiers

IUPAC name methyl 3-amino-2-(5-methoxy-1H-indol-3-yl)propanoate
CAS Number	73758-06-2^Y
PubChem CID	71987
ChemSpider	64989^N
UNII	AV9L041QA4
Chemical and physical data
Formula	C₁₃H₁₆N₂O₃
Molar mass	248.282 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC(=O)C(CN)c1c[nH]c(ccc2OC)c1c2
InChI InChI=1S/C13H16N2O3/c1-17-8-3-4-12-9(5-8)11(7-15-12)10(6-14)13(16)18-2/h3-5,7,10,15H,6,14H2,1-2H3^N Key:YFEDJMLMWJSRJJ-UHFFFAOYSA-N^N
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