Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMARCKD)

• Drug Name: 5-METHOXYTRYPTAMINE Drug Info
• Synonyms: 5-METHOXYTRYPTAMINE; 608-07-1; 2-(5-Methoxy-1H-indol-3-yl)ethanamine; Mexamine; Methoxytryptamine; 3-(2-Aminoethyl)-5-methoxyindole; Mexamine base; 5MOT; 5-Mot; 1H-Indole-3-ethanamine, 5-methoxy-; 2-(5-Methoxyindol-3-yl)ethylamine; Meksamin; Meksamin (free base); 5-MeOT; O-Methylserotonin; 2-(5-Methoxy-1H-Indol-3-Yl)Ethan-1-Amine; NSC 56422; 5-MT; UNII-3VMW6141KC; INDOLE, 3-(2-AMINOETHYL)-5-METHOXY-; 5-methoxy-1H-indole-3-ethanamine; EINECS 210-153-7; Lopac-M-6628; 5-Methoxytryptamine, 97%; BRN 0145587; CHEMBL8165; 3VMW6141KC

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

• Cross-matching ID:
  PubChem CID: 1833
  ChEBI ID: CHEBI:2089
  CAS Number: CAS 608-07-1
  TTD Drug ID: DMARCKD

Molecule-Related Drug Atlas

Drug(s) Targeting 5-HT 6 receptor (HTR6)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
LU AE58054	DMWGRQD	Schizophrenia	6A20	Phase 3	[5]
SB-742457	DM6L4ZT	Alzheimer disease	8A20	Phase 3	[6]
AVN 211	DMVB4OS	Schizophrenia	6A20	Phase 2/3	[7]
SYN120	DMDF7XB	Parkinson disease	8A00.0	Phase 2	[8]
AVN 101	DMJFLBC	Alzheimer disease	8A20	Phase 2	[7]
SYN-120	DMPW0UL	Alzheimer disease	8A20	Phase 2	[9]
PF-05212377	DMPVQYR	Alzheimer disease	8A20	Phase 2	[10]
AVN 322	DMK2LGM	Cognitive impairment	6D71	Phase 2	[6]
SAM-531	DMHVJZ6	Alzheimer disease	8A20	Phase 2	[11]
SUVN-502	DMQD753	Alzheimer disease	8A20	Phase 2	[12]

Drug(s) Targeting 5-HT 2A receptor (HTR2A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Metergolin	DMJFP6G	Hyperprolactinaemia	5A60.1	Approved	[13]
ZOTEPINE	DMF3VXA	Anxiety disorder	6B00-6B0Z	Approved	[14]
Iloperidone	DM6AUFY	Schizophrenia	6A20	Approved	[15]
Flibanserin	DM70DTN	Depression	6A70-6A7Z	Approved	[16]
Lurasidone hydrochloride	DMCVPXO	Schizophrenia	6A20	Approved	[17]
Aniracetam	DMOIFW0	Cerebrovascular ischaemia	8B1Z	Approved	[18]
lumateperone tosylate	DMQ8HOJ	Schizophrenia	6A20	Approved	[19]
Sarpogrelate	DMGLP6S	Diabetic complication	5A2Y	Approved	[20]
Pimavanserin	DMR7IVC	Parkinson disease	8A00.0	Approved	[21]
Zicronapine	DMP8ESD	Schizophrenia	6A20	Phase 3	[22]

Drug(s) Targeting Long transient receptor potential channel 8 (TRPM8)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Menthol	DMG2KW7	Back pain	ME84.Z	Approved	[23]
D-3263	DM7V2OM	Solid tumour/cancer	2A00-2F9Z	Phase 1	[24]
PF-05105679	DM4QPT0	Pain	MG30-MG3Z	Phase 1	[25]
2-APB	DM9AKVR	Discovery agent	N.A.	Investigative	[26]
ACAA	DMACYPW	Discovery agent	N.A.	Investigative	[27]
icilin	DMYVOL9	Discovery agent	N.A.	Investigative	[28]
2-(5-fluoro-1H-indol-3-yl)ethanamine	DMHW5FT	Discovery agent	N.A.	Investigative	[4]
NADA	DM3ORGM	Discovery agent	N.A.	Investigative	[27]
2-(7-(benzyloxy)-1H-indol-3-yl)ethanamine	DMD2QVO	Discovery agent	N.A.	Investigative	[4]
linalool	DMGZQ5P	Discovery agent	N.A.	Investigative	[29]

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
5-HT 2A receptor (HTR2A)	TTJQOD7	5HT2A_HUMAN	Inhibitor	[2]
5-HT 6 receptor (HTR6)	TTJS8PY	5HT6R_HUMAN	Inhibitor	[3]
Long transient receptor potential channel 8 (TRPM8)	TTXDKTO	TRPM8_HUMAN	Inhibitor	[4]

References

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• [2] Central serotonin receptors as targets for drug research. J Med Chem. 1987 Jan;30(1):1-12.
• [3] Medicinal chemistry driven approaches toward novel and selective serotonin 5-HT6 receptor ligands. J Med Chem. 2005 Mar 24;48(6):1781-95.
• [4] 5-benzyloxytryptamine as an antagonist of TRPM8. Bioorg Med Chem Lett. 2010 Dec 1;20(23):7076-9.
• [5] Lu AE58054, a 5-HT6 antagonist, reverses cognitive impairment induced by subchronic phencyclidine in a novel object recognition test in rats. Int J Neuropsychopharmacol. 2010 Sep;13(8):1021-33.
• [6] 5-HT6 receptors and Alzheimer's disease. Alzheimers Res Ther. 2013; 5(2): 15.
• [7] Latrepirdine, a potential novel treatment for Alzheimer's disease and Huntington's chorea. Curr Opin Investig Drugs. 2010 January; 11(1): 80-91.
• [8] Therapeutic strategies for Parkinson disease: beyond dopaminergic drugs. Nat Rev Drug Discov. 2018 Nov;17(11):804-822.
• [9] The Serotonin-6 Receptor as a Novel Therapeutic Target. Exp Neurobiol. 2011 December; 20(4): 159-168.
• [10] PF-05212377 Alzheimer's Disease (Phase 2). Pfizer.
• [11] Activation of 5-HT6 receptors modulates sleep-wake activity and hippocampal theta oscillation. ACS Chem Neurosci. 2013 Jan 16;4(1):191-9.
• [12] Novel and Potent 5-Piperazinyl Methyl-N1-aryl Sulfonyl Indole Derivatives as 5-HT6 Receptor Ligands. ACS Med Chem Lett. 2010 October 14; 1(7): 340-344.
• [13] Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23.
• [14] Current and novel approaches to the drug treatment of schizophrenia. J Med Chem. 2001 Feb 15;44(4):477-501.
• [15] Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
• [16] Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
• [17] Mullard A: 2010 FDA drug approvals. Nat Rev Drug Discov. 2011 Feb;10(2):82-5.
• [18] Anxiolytic effects of aniracetam in three different mouse models of anxiety and the underlying mechanism. Eur J Pharmacol. 2001 May 18;420(1):33-43.
• [19] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
• [20] Beneficial effects of sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, supplemented with pioglitazone on diabetic model mice. Endocr Res. 2009;34(1-2):18-30.
• [21] Pimavanserin, a selective serotonin (5-HT)2A-inverse agonist, enhances the efficacy and safety of risperidone, 2mg/day, but does not enhance efficacy of haloperidol, 2mg/day: comparison with reference dose risperidone, 6mg/day.Schizophr Res.2012 Nov;141(2-3):144-52.
• [22] Clinical pipeline report, company report or official report of Lundbeck.
• [23] TRPV1-mediated itch in seasonal allergic rhinitis. Allergy. 2009 May;64(5):807-10.
• [24] Best of the 2009 AUA Annual Meeting: Highlights from the 2009 Annual Meeting of the American Urological Association, April 25-30, 2009, Chicago, IL. Rev Urol. 2009 Spring; 11(2): 82-107.
• [25] Inhibition of TRPM8 channels reduces pain in the cold pressor test in humans. J Pharmacol Exp Ther. 2014 Nov;351(2):259-69.
• [26] Effects of antagonists and heat on TRPM8 channel currents in dorsal root ganglion neuron activated by nociceptive cold stress and menthol. Neurochem Res. 2012 Feb;37(2):314-20.
• [27] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 500).
• [28] Evolution of thermal response properties in a cold-activated TRP channel. PLoS One. 2009 May 29;4(5):e5741.
• [29] Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Br J Pharmacol. 2004 Feb;141(4):737-45.